Nucleoside dimers analogs containing floxuridine and thymidine with unnatural linker groups: synthesis and cancer line studies. Part III

Abstract

Two series of novel fluorinated nucleosides dimers with an unnatural 1,2,3-triazole linkage were synthesized. The obtained molecules were prepared using “click” chemistry approach based on copper(I) catalyzed Huisgen azide–alkyne cycloaddition. It was performed between 3′- and 5′-azido-nucleosides as the azide components, and the 3′-O- and 5′-O-propargyl-nucleosides as the alkyne components. Based on analysis of the ³ Brunton, L. L.; Lazo, J. S.; Parker, K. L. (Eds.), Goodman & Gilman’s the Pharmacological Basis of Therapeutics, 11th ed.; McGraw-Hill, Medical Publishing Division: New York, NY, 2006. [Google Scholar]J_HH, ³ Brunton, L. L.; Lazo, J. S.; Parker, K. L. (Eds.), Goodman & Gilman’s the Pharmacological Basis of Therapeutics, 11th ed.; McGraw-Hill, Medical Publishing Division: New York, NY, 2006. [Google Scholar]J_H1′C2 and ³ Brunton, L. L.; Lazo, J. S.; Parker, K. L. (Eds.), Goodman & Gilman’s the Pharmacological Basis of Therapeutics, 11th ed.; McGraw-Hill, Medical Publishing Division: New York, NY, 2006. [Google Scholar]J_H1′C6 we estimated conformational preferences of sugar part and orientation around glycosidic bond. All described nucleosides dimers analogs were characterized by spectroscopic methods and evaluated for their in vitro cytotoxicity in three human cancer cell lines: cervical (HeLa), oral (KB) and breast (MCF-7).     

MOLECULAR MODELLING OF 2′-OH MEDIATED HYDROGEN BONDING IN RIBONUCLEOS(T)IDES BY NMR CONSTRAINED AM1 AND MMX CALCULATIONS

The intra- and intermolecular hydrogen bonding (ΔGº_298K ≈ 2, kcal mol^?1) of 2′-OH in nucleos(t)ides has been reported by the temperature- and concentration-dependent NMR study in conjunction with dihedral dependence of the NMR derived both endo (³ J _H,H)- and exocyclic (³ JH,OH) coupling constants, nOe contacts and lineshape analyses of hydroxyl protons for EtpA (1), 3′-dA (2), rA (3), 2′-dA (4) [Fig. 1] in DMSO-d ₆ at 500 MHz.

MOLECULAR MODELLING OF 2′-OH MEDIATED HYDROGEN BONDING IN RIBONUCLEOS(T)IDES BY NMR CONSTRAINED AM1 AND MMX CALCULATIONS

All authors

Parag Acharya, Irina Velikian, Sandipta Acharya & Jyoti Chattopadhyaya

https://doi.org/10.1081/NCN-100002521

Published online:

07 February 2007

Figure 1. The schematic representation of the bias of the dymanic two-state pseudorotational equilibrium between the North-type (N, C2′-exo -C3′-endo) and the South-type (S, C3′-exo-C2′-endo) [3a] Thibaudeau, C. and Chattopadhyaya, J. 1999. Stereoelectronic Effects in Nucleosides and Nucleotides and their Structural Implications Sweden: (ISBN 91-506-1351-0), Department of Bioorganic Chemistry, Uppsala University Press (fax: +4618554495). For review see: and references therein [Google Scholar] pseudorotamers of the sugar moeity for EtpA (1), 3′-dA (2), rA (3), 2′-dA (4) and torsion (Φ) around C2′/3′-O bond viz. Φ₁ = Φ_{H2′?C2′?O?H} and Φ₂ = Φ_{H3′?C3′?O?H} except in 1 where the torsion across C3′-O3′ bond is actually ?^? [C4′-C3′-O3′-P].     

3.

DNA binding,photocleavage, antimicrobial and cytotoxic properties of Ru(II) polypyridyl complexes containing BOPIP ligand, (BOPIP = {2-(4-(benzyloxy) phenyl)-1H-imidazo [4,5-f] [1,2]phenanthroline})     

Srinivas Gopu  Vuradi Ravi kumar  Kotha Laxma Reddy  Putta Venkat Reddy 《Nucleosides, nucleotides & nucleic acids》2019,38(5):349-373

A novel ligand BOPIP (BOPIP?=?{2-(4-(benzyloxy)phenyl)-1H-imidazo[4,5-f][1,10]phenanthroline}) and its mononuclear Ru(II) polypyridyl complexes [Ru(phen)₂ BOPIP]²⁺(1) (phen?=?1,10-Phenanthrolene), [Ru(bpy)₂ BOPIP]²⁺(2) (bpy?=?2,2′ bipyridyl), [Ru(dmb)₂ BOPIP]²⁺(3) (dmb?=?4, 4′ -dimethyl 2, 2′ -bipyridine), [Ru(Hdpa)₂ BOPIP]²⁺(4) (Hdpa?=?2,2′dipyridylamine) have been synthesized successfully and characterized by elemental analysis, UV-vis, IR, ¹H, ¹³ Gill, M. R.; Garcia-Lara, J.; Foster, S. J.; Smythe, C.; Battaglia, G.; Thomas, J. A. A Ruthenium(II) polypyridyl Complex for Direct Imaging of DNA Structure in Living Cells. Nat. Chem. 2009, 1, 662–667.[Crossref], [PubMed], [Web of Science ®] , [Google Scholar]C-NMR, and ESI-MS Spectroscopy. The interaction of these complexes with CT-DNA was studied using absorption, emission techniques, viscosity measurements and molecular docking studies. The docking study also supports the binding ability of complexes obtained through the absorption and emission techniques. These studies reveal that the Four Ru(II) polypyridyl complexes bind to DNA predominantly by intercalation. The Antimicrobial activity and cytotoxicity of these complexes are also reported.     

4.

Rnai Activity of Sirnas Modified with 2′-Aminoalkyl-Substituted Fluorinated Nucleobases     

Jens Haas  Thea Mueller-Kuller  Stefan Klein  Joachim W. Engels 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):865-868

We recently reported that a 1′-deoxy-1′-(4,6-difluoro-1H-benzimidazol-1-yl)-2′-(β-aminoethyl)-β-d-ribofuranose nucleoside appears to be a universal nucleoside which does not differentiate between the four natural nucleosides A, C, G, and U in duplexes. Moreover, ribozymes modified with this nucleoside analog showed a better or at least equal catalytic activity relative to Watson-Crick mismatches.^{[ 1} Klöpffer, A. E. and Engels, J. W. 2004. Synthesis of 2′-aminoalkyl substituted fluorinated nucleobases and their influence on the kinetic properties of hammerhead ribozymes. ChemBioChem, 5: 100–109.  [Google Scholar] ^] Due to these data, we investigated the ability of this compound to tolerate Watson-Crick mismatches in order to avoid HIV escape mutations in RNA interference. The influence of this nucleoside analog on siRNA efficiency was analyzed with a proven siRNA targeting GFP.     

5.

2′,3′-Dideoxynucleoside 5′-β,γ-(Difluoromethylene) Triphosphates With α-P-Thio or α-P-Seleno Modifications: Synthesis and Their Inhibition of HIV-1 Reverse Transcriptase     

Nicholas A. Boyle  Patrick Fagan  Jennifer L. Brooks  Marija Prhavc  John Lambert  P. Dan Cook 《Nucleosides, nucleotides & nucleic acids》2013,32(10-12):1651-1664

     

6.

Synthesis and antimicrobial activity of novel 1,4,5-triphenyl-1<Emphasis Type="Italic">H</Emphasis>-imidazol-[1,2,3]-triazole derivatives     

B.?Sathish?Kumar  B.?S.?Veena  P.?V.?Anantha LakshmiEmail author  L.?Kamala  E.?Sujatha 《Russian Journal of Bioorganic Chemistry》2017,43(5):589-594

Novel 1-phenyl-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole derivatives were synthesized by click chemistry reaction and screened for antimicrobial activity against grampositive and gram-negative bacterial and fungal species. All the compounds were characterized by ¹H and ¹³C NMR, IR, and mass spectral data. The results of antibacterial study indicated that 1-(4-nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole, 1-(4-(4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)phenyl)ethanone, 1-(2,6-dichloro-4-nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole, and 1-(2-methoxy-4-nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole showed appreciable antibacterial activity while 1-(4-fluorophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy) methyl)-1H-1,2,3-triazole, 1-(2,6-dichloro-4-nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole, and 1-(4-methoxyphenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole emerged as the most potential antifungal agents.     

7.

NOVEL SYNTHESIS OF seco TYPE OF ACYCLO C-NUCLEOSIDES OF 1,2,4-TRIAZOLE AND 1,2,4-TRIAZOLO[3,4-b][1,3,4]THIADIAZINE     

《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):103-116

The seco C-nucleosides 3-(1,2,3,4,5-penta-O-acetyl-D-gluco- and D- galacto-pentitol-1-yl)-1H-1,2,4-triazoles (8 and 9) were obtained in a one pot by deamination and dethiolation of 4-amino-3-(D-gluco- and D-galacto-pentitol-1-yl)-5-mercapto-1,2,4-triazoles (1 and 2), respectively, using sodium nitrite in orthophosphoric acid and subsequent acetylation. Condensation of 1, 2, and 4-amino-3-(D-glycero-D-gulo-hexitol-1-yl)-5-mercapto-1,2,4-triazole (12) with phenacylbromide (11) afforded the corresponding 3-(D-gluco-, D-galacto-pentitol-1-yl) and 3-(D-glycero-D-gulo-hexitol-1-yl)-6-phenyl-7H-1,2,4- triazolo[3,4-b][1,3,4] thiadiazines (15, 16, and 17). Acetylation of 15–17 gave the penta- and hexa-O-acetyl derivatives 18–20, respectively. The structures were confirmed by using ¹H, ¹³C, and 2D NMR spectra, DQFCOSY, HMQC, and HMBC experiments. The favored conformational structures were deduced from the vicinal coupling constants of the protons.     

8.

Synthesis and Biological Evaluation of Some Acyclic 4,6-Disubstituted 1H-Pyrazolo[3,4-d]pyrimidine Nucleosides     

《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):967-972

Abstract

The chemical synthesis and biological evaluation of some acyclic α-[6-(1′-carbamoylalkylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]thioalkylamide nucleosides are described.     

9.

Synthesis of Fused Cyclopropane-Containing Nucleosides by [1,2]-Hydride Shift Rearrangements and B-Elimination Reactions of Sulfonylated Ribonucleosides     

Masajiro Kawana  Hiroyoshi Kuzuhara 《Nucleosides, nucleotides & nucleic acids》2013,32(2-4):551-569

Abstract

(1′R, 3′S and R, 5′S)-4′-Oxo-2′-oxabicyclo[3.1.0]hexan-3′-yl pyrimidines and purines were synthesized from ribonucleosides in 2-5 steps. The configurations of the base moieties in the cyclopropano keto-nucleosides were determined by NOE difference spectroscopy.     

10.

Isatin 1,2,3-triazoles as potent inhibitors against caspase-3     

Jiang Y  Hansen TV 《Bioorganic & medicinal chemistry letters》2011,21(6):1626-1629

Sixteen disubstituted 1,2,3-triazoles were prepared using the Huisgen cycloaddition reaction and evaluated as inhibitors against caspase-3. The two most potent inhibitors were found to be (S)-1-((1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-1,2,3-triazol-4-yl)methyl)-5-((2-(methoxymethyl)pyrrolidin-1-yl)sulfonyl)indoline-2,3-dione (7f) and (S)-1-((1-benzyl-1H-1,2,3-triazol-5-yl)methyl)-5-((2-(methoxymethyl)pyrrolidin-1-yl)sulfonyl)indoline-2,3-dione (8g) with IC₅₀-values of 17 and 9 nM, respectively. Lineweaver-Burk plots revealed that these two triazoles show competitive inhibitory mechanism against caspase-3.     

11.

EFFICIENT SYNTHESIS OF FUSED ISOTHIAZOLO C-NUCLEOSIDES. III. SYNTHESIS OF 7-SUBSTITUTED ISOTHIAZOLO[4,5-d]PYRIMIDINE C-NUCLEOSIDES*     

《Nucleosides, nucleotides & nucleic acids》2013,32(3):229-241

The Divakar-Reese procedure has been successfully applied for transforming 7-oxo-isothiazolo[4,5-d]pyrimidine C-nucleosides (4a,b, 5a,b, 6a) via 1,2,4-triazol-1-yl intermediates (7a,b, 8a,b) into various 7-substituted C-nucle- osides 15a,b, 16a,b, 17a, 18a, 19a,b, 20a,b; their subsequent deprotection provides novel types of unusual C-glycosides 22b, 23a, 24a,b, 25b, 26b.

C-Nucleosides, possessing on its heterocyclic base other than naturally occuring oxo- or amino substituents, are important model compounds for biological or medicinal studies [2a] Hanessian, S. and Pernet, A. G. 1976. Adv. Carbohydr. Chem. Biochem., 32: 111–188. cf. [Google Scholar], [2b] Mizuno, Y. 1986. The Organic Chemistry of Nucleic Acids Amsterdam: Elsevier.  [Google Scholar], [2c] Huryn, D. M. and Okabe, M. 1992. Chem. Rev., 92: 1745–1768. [Crossref], [Web of Science ®] , [Google Scholar], [2d] Häbich, D. 1991. Chem. in uns. Zeit, 25: 295–307.  [Google Scholar], [2e] Uhlmann, E. and Peyman, A. 1990. Chem. Rev., 90: 543–584. [Crossref], [Web of Science ®] , [Google Scholar], [2f] Thuong, N. T. and Helene, C. 1993. Angew. Chem., 105: 697–723. [Crossref] , [Google Scholar], [2g] 1993. Angew. Chem. Int. Ed. Engl., 33: 666–690.  [Google Scholar], [2h] Yarchoan, R., Mitsuya, H., Zhomas, R. V., Pluda, J. M., Hartman, N. R., Perno, C. F., Marczyk, K. S., Allain, J. P., Johns, D. G. and Broder, S. 1989. Science, 245: 412–414. [Crossref], [PubMed], [Web of Science ®] , [Google Scholar], [2i] Tanaka, H., Baba, M., Hayakawa, H., Sakamaki, T., Miyasaka, T., Ubasawa, M., Takashima, H., Sekiya, E., Nitta, I., Shigeta, S., Walker, R. T., Balzarini, J. and De Clerq, E. 1991. J. Med. Chem., 34: 349–357. [Crossref], [PubMed], [Web of Science ®] , [Google Scholar] [3a] Koyama, G., Maeda, K., Umezawa, H. and Iitaka, Y. 1966. Tetrahedron Lett., : 597–602. Some C-glycosides with antibiotic, antiviral (HIV), and anticancer activities [Google Scholar], [3b] Hori, M., Wakashiro, T., Ito, E., Sawa, T., Takeuchi, T. and Umezawa, H. J. 1968. J. Antibiot., 21A: 264–270. [Chem. Abstr. 1968, 69, 11356j] [Google Scholar], [3c] Farkas, J. and ?orm. 1972. F. Collect. Czech. Chem. Commun., 37: 2798–2803.  [Google Scholar], [3d] Acton, E. M., Ryan, K. J., Henry, D. W. and Goodman, L. 1971. J. Chem. Soc., Chem. Commun., : 986–988.  [Google Scholar], [3e] Nakagawa, Y., Kano, H., Tsukuda, Y. and Koyama, H. 1967. Tetrahedron Lett., : 4105–4109.  [Google Scholar], [3f] Inoue, I. and Kuwaijama, I. 1980. J. Chem. Soc., Chem. Commun., : 251–253.  [Google Scholar], [3g] Buchanan, J. G., Stobie, A. and Wightman, R. H. 1980. ibid., : 916–917. [Crossref] , [Google Scholar], [3h] Hildebrand, S. and Leumann, C. 1996. Angew. Chem., 108: 2100–2102. Angew. Chem. Int. Ed. Engl. 1996, 35, 1968–1970 [Google Scholar]. We want to report on the synthesis of novel 7-substituted isothiazolo = [4,5-d]pyrimidine C-nucleosides. As we could show in previous papers [1] Wamhoff, H., Berressem, R. and Nieger, M. 1994. J. Org. Chem., 59: 1912–1917. Part 2 [Google Scholar], [4] Wamhoff, H., Berressem, R. and Nieger. 1993. M. J. Org. Chem., 58: 5181–5185.  [Google Scholar], there exists a simple approach to the protected C-glycosides 4–6.

     

12.

Oligonucleotides Containing Disaccharide Nucleosides: Synthesis,Physicochemical, and Substrate Properties     

《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1117-1118

Abstract

The efficient synthesis of oligonucleotides containing 2′-O-β-D-ribofuranosyl (and β-D-ribopyranosyl)nucleosides, 2′-O-α-D-arabinofuranosyl (and α-L-arabinofuranosyl)nucleosides, 2′-O-β-D-erythrofuranosylnucleosides, and 2′-O-(5′-amino-5-deoxy-β-D-ribofuranosyl)nucleosides have been developed.     

13.

Redefinition of the hypotrichous ciliate Uncinata,with descriptions of the morphology and phylogeny of three urostylids (Protista,Ciliophora)     

Xiaotian Luo  Feng Gao  Khaled A. S. Al-Rasheid  Alan Warren  Weibo Song 《分类学与生物多样性》2013,11(5):455-471

We investigated the morphology, morphogenesis and small subunit rRNA gene-based phylogeny of three marine urostylids, Uncinata gigantea Bullington, 1940 Bullington, W. E. (1940). Some ciliates from Tortugas. Papers from the Tortugas Laboratory, 32, 179–221. [Google Scholar], Holosticha heterofoissneri Hu & Song, 2001 Hu, X., & Song, W. (2001). Morphology and morphogenesis of Holosticha heterofoissneri n. sp. from the Yellow Sea, China (Ciliophora, Hypotrichida). Hydrobiologia, 448, 171–179. doi:10.1023/A:1017553406031.[Crossref], [Web of Science ®] , [Google Scholar], and Holosticha cf. heterofoissneri. The dorsal morphogenesis of Uncinata gigantea shows de novo formation of two groups of anlagen near the marginal rows. Holosticha cf. heterofoissneri demonstrates fragmentation of the first dorsal kinety anlage as in Holosticha heterofoissneri. Our population of H. heterofoissneri corresponds well with previously described populations in terms of its general morphology and ciliary pattern. Uncinata gigantea can be recognized by its large and highly contractile body, yellowish to brownish cell colour, two types of cortical granules, and 20–30 transversely oriented and densely arranged cirri in the left marginal row, which often overlie the buccal vertex. Based on the new data, especially infraciliature, the genus Uncinata is here redefined. Both the morphology and phylogenetic analyses suggest that the genus Uncinata should be classified within the family Urostylidae. In addition, both morphological and morphogenetic data suggest that Holosticha bradburyae Gong et al., 2001 Gong, J., Song, W., Hu, X., Ma, H., & Zhu, M. (2001). Morphology and infraciliature of Holosticha bradburyae n. sp. (Ciliophora, Hypotrichida) from the Yellow Sea, China. Hydrobiologia, 464, 63–69. doi:10.1023/A:1013901621439.[Crossref], [Web of Science ®] , [Google Scholar] should be transferred to Uncinata as U. bradburyae (Gong et al., 2001 Gong, J., Song, W., Hu, X., Ma, H., & Zhu, M. (2001). Morphology and infraciliature of Holosticha bradburyae n. sp. (Ciliophora, Hypotrichida) from the Yellow Sea, China. Hydrobiologia, 464, 63–69. doi:10.1023/A:1013901621439.[Crossref], [Web of Science ®] , [Google Scholar]) comb. nov., due to its possession of a characteristically prominent beak-like, leftwards curved projection and the developmental mode of the dorsal kineties. This assignment is supported by the phylogenetic analyses, which placed Uncinata gigantea in a clade with U. bradburyae (Gong et al., 2001 Gong, J., Song, W., Hu, X., Ma, H., & Zhu, M. (2001). Morphology and infraciliature of Holosticha bradburyae n. sp. (Ciliophora, Hypotrichida) from the Yellow Sea, China. Hydrobiologia, 464, 63–69. doi:10.1023/A:1013901621439.[Crossref], [Web of Science ®] , [Google Scholar]) comb. nov., and revealed only 1.13% (19 bp) difference in their SSU-rDNA gene sequence.     

14.

Cooked Odor of Euphausia pacifica Hansen     

Kikue Kubota  Akio Kobayashi  Tei Yamanishi 《Bioscience, biotechnology, and biochemistry》2013,77(11):2753-2754

Quinoxaline and benzimidazole derivatives obtained from L-rhamnose and L-fucose under deoxygenated, weakly acidic, heated conditions were studied using GLC, HPLC, and NMR.

Four quinoxalines and one benzimidazole were obtained from L-rhamnose (RHA-I, II, III, III′, and IV) and L-fucose (FUA-I, II, III, IV, and V) in an acidic solution (MeOH-AcOH-H₂I = 8 : 1 : 2) at 80°C. The total yield of the products as sugar was about 80% from either rhamnose or fucose.

The structure of RHA-I was (2′S)-2-methyl-3-(2′-hydroxypropyl)quinoxaline; RHA-II, (2′R,3′S)-2-(2′,3′-dihydroxybutyl)quinoxaline; RHA-III, (1′S,2′S,3′S)-2-(1′2′3′-trihydroxybutyl)quinoxaline[2-(L-arabino-1′,2′,3′-trihydroxybutyl)quinoxaline]; RHA-III′, 2-(L-ribo-1′,2′,3′-trihydroxybutyl)quinoxaline; and RHA-IV, 2-(L-manno-1′,2′,3′,4′-tetrahydroxypentyl)-benzimidazole, and the structure of FUA-I was the same as RHA-I; FUA-II, (2′S, 3′S)-2-(2′, 3′-dihydroxybutyl)quinoxaline; FUA-III, (1′R, 2′R, 3′S)-2-(1′,2′,3′-trihydroxybutyl)quinoxaline [2-(L-xylo-1′,2′,3′-trihydroxybutyl)quinoxaline; FUA-IV, 2-(L-lyxo-1′,2′,3′-trihydroxybutyl)-quinoxaline; and FUA-V, 2-(L-galacto-1′,2′,3′,4′-tetrahydroxypentyl)benzimidazole. These results suggest no significant difference for the pathways of quinoxaline and benzimidazole formation between L-rhamnose and L-fucose. Possible pathways are proposed for each sugar.     

15.

Synthesis, crystal structure, solution behavior and catalytic activity of a palladium(II)-allyl complex containing a 2-pyridyl-1,2,3-triazole bidentate ligand     

E. Amadio  A. Scrivanti  G. Chessa  U. Matteoli  A. Dolmella 《Inorganica chimica acta》2011,370(1):388-12124

The synthesis and characterization of the cationic complex [Pd(η³-C₃H₅)(2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)pyridine)](BF₄) (2) are reported. The solid-state structure of 2 has been unambiguously confirmed by single-crystal X-ray diffraction analysis. ¹H NMR spectroscopy reveals that in solution complex 2 is dynamic and that syn-syn, anti-anti exchange of the allyl protons occurs. Complex 2 exhibits good activity in the Suzuki-Miyaura coupling of aryl bromides with phenyl boronic acid.     

16.

An annotated checklist of Iranian aquatic Polyphaga: Georissidae,Helophoridae, Hydrochidae,Spercheidae, Curculionidae and Erirhinidae (Insecta: Coleoptera)     

Mustafa C. Darilmaz  Hadi Ostovan  Hassan Ghahari  Robert B. Angus 《水生昆虫》2013,35(4):389-406

Abstract

The checklist comprises all species of six families of Iranian aquatic Polyphaga (Coleoptera). In total, 43 species/subspecies within the families, Georissidae (one species), Helophoridae (25 species and two subspecies), Hydrochidae (three species), Spercheidae (one species), Curculionidae (nine species) and Erirhinidae (two species) are listed for the fauna of Iran. Helophorus (Rhopalohelophorus) nanus Sturm, 1836 Sturm, J. (1836), Deulschlands Fauna in Abbildungen nach der Natur mit Beschreibungen. V. Abtheilung. Die Inseclen. Zehntes Bändchen. Käfer, Nürnberg: J. Sturm, 108 pp., pl. 216–227. (also under title: Deutschlands Insecten, Käfer). [Google Scholar] (Helophoridae) is recorded for the first time from Iran. We also present two additional species lists: one with incorrect records (one species) and the other with unidentified species.     

17.

The genera Stegastopsis Kraatz, 1865 and Orostegastopsis Koch, 1962 with description of O. planioculata sp. n. from Oman (Coleoptera: Tenebrionidae: Tentyriini)     

Martin Lillig 《Zoology in the Middle East.》2013,59(4):345-352

The first Asian member of Orostegastopsis Koch, 1962 Koch, C. (1962): Vierter taxonomischer Beitrag zur Kenntnis der Tenebrioniden Somalias: Über die von Prof. G. Scortecci 1953 und 1957 in der Migiurtinia-Provinz gesammelten Arten. 1. Teil. Atti della Società Italiana di Scienze Naturali, 51, 237–270. [Google Scholar] is described and figured: O. planioculata sp. n., which can be easily distinguished from the two Somalian species O. scorteccii Koch, 1962 Koch, C. (1962): Vierter taxonomischer Beitrag zur Kenntnis der Tenebrioniden Somalias: Über die von Prof. G. Scortecci 1953 und 1957 in der Migiurtinia-Provinz gesammelten Arten. 1. Teil. Atti della Società Italiana di Scienze Naturali, 51, 237–270. [Google Scholar] and O. kaszabi (Bremer, 1985 Bremer, H. J. (1985): Eine neue Stegastopsis-Art (Coleopt., Tenebrionidae, Tentyriini) aus Somalia. Entomologische Blätter, 81, 59–61. [Google Scholar]) comb. nov. by the shallow eyes. According to the shape of the clypeus, Stegastopsis kaszabi Bremer, 1985 Bremer, H. J. (1985): Eine neue Stegastopsis-Art (Coleopt., Tenebrionidae, Tentyriini) aus Somalia. Entomologische Blätter, 81, 59–61. [Google Scholar] is transferred from the genus Stegastopsis Kraatz to the genus Orostegastopsis Koch as was already indicated by Bremer (1985 Bremer, H. J. (1985): Eine neue Stegastopsis-Art (Coleopt., Tenebrionidae, Tentyriini) aus Somalia. Entomologische Blätter, 81, 59–61. [Google Scholar]) who treated Orostegastopsis as a subgenus of Stegastopsis: Orostegastopsis kaszabi (Bremer, 1985 Bremer, H. J. (1985): Eine neue Stegastopsis-Art (Coleopt., Tenebrionidae, Tentyriini) aus Somalia. Entomologische Blätter, 81, 59–61. [Google Scholar]) comb. nov. Keys to the species of Stegastopsis and Orostegastopsis are given.     

18.

New records of Hydrochus Leach, 1817 (Coleoptera: Hydrochidae) from Iran     

Hiva Nasserzadeh  Manfred A. Jäch  Jalal Shirazi 《水生昆虫》2013,35(4):370-374

Abstract

Hydrochus ignicollis Motschulsky, 1860 Motschulsky, V. de (1860), ‘Coléoptères rapportés de la Sibérie orientale et notamment des pays situés sur les bords du fleuve Amour par MM. Schrenck, Maack, Ditmar, Voznessenski etc.’, in Reisen und Forschungen im Amur - Lande in den Jahren 1854–1856 im Auftrage der Kaiserl. Akademie der Wissenschaften zu St. Petersburg ausgeführt und in Verbindung mit mehreren Gelehrten herausgegeben. Band II. ed. L. Schrenck , Zweite Lieferung . Coleopteren, St. Petersburg: Eggers und Comp., pp. 80–257, pls. VI–XI. [Google Scholar] is recorded from Iran (Gilan Province) for the first time. In addition, new Iranian provincial records are provided for two species: H. nodulifer Reitter, 1897 Reitter, E . (1897), ‘Dreißig neue Coleopteren aus russisch Asien und der Mongolei’, Deutsche Entomologische Zeitschrift , 1897(2), 209–228. [Google Scholar] (Zanjan Province) and H. farsicus Hidalgo-Galiana, Jäch, and Ribera, 2010 Hidalgo-Galiana, A. , Jäch, M.A. , and Ribera, I . (2010), ‘ Hydrochus farsicus sp. n. from Iran and Notes on other Palearctic Species of the Genus (Coleoptera: Hydrophiloidea: Hydrochidae)’, Zootaxa , 2344, 61–64.[Crossref] , [Google Scholar] (Kohgiluyeh and Boyer-Ahmad Province). Photographs of the habitus, the male genitalia and the habitat of H. ignicollis are provided.     

19.

Diversity of the karyorelictid ciliates: Remanella (Protozoa,Ciliophora, Karyorelictida) inhabiting intertidal areas of Qingdao,China, with descriptions of three species     

Yuan Xu  Miao Miao  Alan Warren  Weibo Song 《分类学与生物多样性》2013,11(2):207-219

     

20.

6-Azathymidine-4′-thionucleosides: synthesis and antiviral evaluation     

Malina Jasamai  Jan Balzarini  Claire Simons 《Journal of enzyme inhibition and medicinal chemistry》2013,28(1):56-61

The synthesis of dideoxy-6-azathymidine 4′-thionucleoside 1-(2,3-dideoxy-4-thio-β-D-erythro-pentofuranosyl)-(6-azathymidine) (2), and the L-nucleoside, 1-(4-thio-β-L-erythro-pentofuranosyl)-(6-azathymidine) (3) and their evaluation against a wide panel of antiviral assays are described. The L-thionucleoside (3) was devoid of antiviral activity. The dideoxy-thionucleoside (2) was moderately active against vaccinia virus (VV) and the herpes simplex virus strains HSV-1 (strain KOS) and HSV-2 (strain G) (MIC 12 μM) and retained inhibitory activity vs a thymidine kinase-deficient strain HSV-1/TK^–, suggesting that (2) is not dependent on viral TK-catalysed phosphorylation for antiviral activity and/or may use an alternative metabolic activation pathway.     

DNA binding,photocleavage, antimicrobial and cytotoxic properties of Ru(II) polypyridyl complexes containing BOPIP ligand, (BOPIP = {2-(4-(benzyloxy) phenyl)-1H-imidazo [4,5-f] [1,2]phenanthroline})

A novel ligand BOPIP (BOPIP?=?{2-(4-(benzyloxy)phenyl)-1H-imidazo[4,5-f][1,10]phenanthroline}) and its mononuclear Ru(II) polypyridyl complexes [Ru(phen)₂ BOPIP]²⁺(1) (phen?=?1,10-Phenanthrolene), [Ru(bpy)₂ BOPIP]²⁺(2) (bpy?=?2,2′ bipyridyl), [Ru(dmb)₂ BOPIP]²⁺(3) (dmb?=?4, 4′ -dimethyl 2, 2′ -bipyridine), [Ru(Hdpa)₂ BOPIP]²⁺(4) (Hdpa?=?2,2′dipyridylamine) have been synthesized successfully and characterized by elemental analysis, UV-vis, IR, ¹H, ¹³ Gill, M. R.; Garcia-Lara, J.; Foster, S. J.; Smythe, C.; Battaglia, G.; Thomas, J. A. A Ruthenium(II) polypyridyl Complex for Direct Imaging of DNA Structure in Living Cells. Nat. Chem. 2009, 1, 662–667.[Crossref], [PubMed], [Web of Science ®] , [Google Scholar]C-NMR, and ESI-MS Spectroscopy. The interaction of these complexes with CT-DNA was studied using absorption, emission techniques, viscosity measurements and molecular docking studies. The docking study also supports the binding ability of complexes obtained through the absorption and emission techniques. These studies reveal that the Four Ru(II) polypyridyl complexes bind to DNA predominantly by intercalation. The Antimicrobial activity and cytotoxicity of these complexes are also reported.     

Rnai Activity of Sirnas Modified with 2′-Aminoalkyl-Substituted Fluorinated Nucleobases

We recently reported that a 1′-deoxy-1′-(4,6-difluoro-1H-benzimidazol-1-yl)-2′-(β-aminoethyl)-β-d-ribofuranose nucleoside appears to be a universal nucleoside which does not differentiate between the four natural nucleosides A, C, G, and U in duplexes. Moreover, ribozymes modified with this nucleoside analog showed a better or at least equal catalytic activity relative to Watson-Crick mismatches.^{[ 1} Klöpffer, A. E. and Engels, J. W. 2004. Synthesis of 2′-aminoalkyl substituted fluorinated nucleobases and their influence on the kinetic properties of hammerhead ribozymes. ChemBioChem, 5: 100–109.  [Google Scholar] ^] Due to these data, we investigated the ability of this compound to tolerate Watson-Crick mismatches in order to avoid HIV escape mutations in RNA interference. The influence of this nucleoside analog on siRNA efficiency was analyzed with a proven siRNA targeting GFP.     

Synthesis and antimicrobial activity of novel 1,4,5-triphenyl-1<Emphasis Type="Italic">H</Emphasis>-imidazol-[1,2,3]-triazole derivatives

Novel 1-phenyl-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole derivatives were synthesized by click chemistry reaction and screened for antimicrobial activity against grampositive and gram-negative bacterial and fungal species. All the compounds were characterized by ¹H and ¹³C NMR, IR, and mass spectral data. The results of antibacterial study indicated that 1-(4-nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole, 1-(4-(4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)phenyl)ethanone, 1-(2,6-dichloro-4-nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole, and 1-(2-methoxy-4-nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole showed appreciable antibacterial activity while 1-(4-fluorophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy) methyl)-1H-1,2,3-triazole, 1-(2,6-dichloro-4-nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole, and 1-(4-methoxyphenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole emerged as the most potential antifungal agents.     

NOVEL SYNTHESIS OF seco TYPE OF ACYCLO C-NUCLEOSIDES OF 1,2,4-TRIAZOLE AND 1,2,4-TRIAZOLO[3,4-b][1,3,4]THIADIAZINE

The seco C-nucleosides 3-(1,2,3,4,5-penta-O-acetyl-D-gluco- and D- galacto-pentitol-1-yl)-1H-1,2,4-triazoles (8 and 9) were obtained in a one pot by deamination and dethiolation of 4-amino-3-(D-gluco- and D-galacto-pentitol-1-yl)-5-mercapto-1,2,4-triazoles (1 and 2), respectively, using sodium nitrite in orthophosphoric acid and subsequent acetylation. Condensation of 1, 2, and 4-amino-3-(D-glycero-D-gulo-hexitol-1-yl)-5-mercapto-1,2,4-triazole (12) with phenacylbromide (11) afforded the corresponding 3-(D-gluco-, D-galacto-pentitol-1-yl) and 3-(D-glycero-D-gulo-hexitol-1-yl)-6-phenyl-7H-1,2,4- triazolo[3,4-b][1,3,4] thiadiazines (15, 16, and 17). Acetylation of 15–17 gave the penta- and hexa-O-acetyl derivatives 18–20, respectively. The structures were confirmed by using ¹H, ¹³C, and 2D NMR spectra, DQFCOSY, HMQC, and HMBC experiments. The favored conformational structures were deduced from the vicinal coupling constants of the protons.     

Synthesis and Biological Evaluation of Some Acyclic 4,6-Disubstituted 1H-Pyrazolo[3,4-d]pyrimidine Nucleosides

Abstract

The chemical synthesis and biological evaluation of some acyclic α-[6-(1′-carbamoylalkylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]thioalkylamide nucleosides are described.     

Synthesis of Fused Cyclopropane-Containing Nucleosides by [1,2]-Hydride Shift Rearrangements and B-Elimination Reactions of Sulfonylated Ribonucleosides

Abstract

(1′R, 3′S and R, 5′S)-4′-Oxo-2′-oxabicyclo[3.1.0]hexan-3′-yl pyrimidines and purines were synthesized from ribonucleosides in 2-5 steps. The configurations of the base moieties in the cyclopropano keto-nucleosides were determined by NOE difference spectroscopy.     

Isatin 1,2,3-triazoles as potent inhibitors against caspase-3

Sixteen disubstituted 1,2,3-triazoles were prepared using the Huisgen cycloaddition reaction and evaluated as inhibitors against caspase-3. The two most potent inhibitors were found to be (S)-1-((1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-1,2,3-triazol-4-yl)methyl)-5-((2-(methoxymethyl)pyrrolidin-1-yl)sulfonyl)indoline-2,3-dione (7f) and (S)-1-((1-benzyl-1H-1,2,3-triazol-5-yl)methyl)-5-((2-(methoxymethyl)pyrrolidin-1-yl)sulfonyl)indoline-2,3-dione (8g) with IC₅₀-values of 17 and 9 nM, respectively. Lineweaver-Burk plots revealed that these two triazoles show competitive inhibitory mechanism against caspase-3.     

EFFICIENT SYNTHESIS OF FUSED ISOTHIAZOLO C-NUCLEOSIDES. III. SYNTHESIS OF 7-SUBSTITUTED ISOTHIAZOLO[4,5-d]PYRIMIDINE C-NUCLEOSIDES*

The Divakar-Reese procedure has been successfully applied for transforming 7-oxo-isothiazolo[4,5-d]pyrimidine C-nucleosides (4a,b, 5a,b, 6a) via 1,2,4-triazol-1-yl intermediates (7a,b, 8a,b) into various 7-substituted C-nucle- osides 15a,b, 16a,b, 17a, 18a, 19a,b, 20a,b; their subsequent deprotection provides novel types of unusual C-glycosides 22b, 23a, 24a,b, 25b, 26b.

C-Nucleosides, possessing on its heterocyclic base other than naturally occuring oxo- or amino substituents, are important model compounds for biological or medicinal studies [2a] Hanessian, S. and Pernet, A. G. 1976. Adv. Carbohydr. Chem. Biochem., 32: 111–188. cf. [Google Scholar], [2b] Mizuno, Y. 1986. The Organic Chemistry of Nucleic Acids Amsterdam: Elsevier.  [Google Scholar], [2c] Huryn, D. M. and Okabe, M. 1992. Chem. Rev., 92: 1745–1768. [Crossref], [Web of Science ®] , [Google Scholar], [2d] Häbich, D. 1991. Chem. in uns. Zeit, 25: 295–307.  [Google Scholar], [2e] Uhlmann, E. and Peyman, A. 1990. Chem. Rev., 90: 543–584. [Crossref], [Web of Science ®] , [Google Scholar], [2f] Thuong, N. T. and Helene, C. 1993. Angew. Chem., 105: 697–723. [Crossref] , [Google Scholar], [2g] 1993. Angew. Chem. Int. Ed. Engl., 33: 666–690.  [Google Scholar], [2h] Yarchoan, R., Mitsuya, H., Zhomas, R. V., Pluda, J. M., Hartman, N. R., Perno, C. F., Marczyk, K. S., Allain, J. P., Johns, D. G. and Broder, S. 1989. Science, 245: 412–414. [Crossref], [PubMed], [Web of Science ®] , [Google Scholar], [2i] Tanaka, H., Baba, M., Hayakawa, H., Sakamaki, T., Miyasaka, T., Ubasawa, M., Takashima, H., Sekiya, E., Nitta, I., Shigeta, S., Walker, R. T., Balzarini, J. and De Clerq, E. 1991. J. Med. Chem., 34: 349–357. [Crossref], [PubMed], [Web of Science ®] , [Google Scholar] [3a] Koyama, G., Maeda, K., Umezawa, H. and Iitaka, Y. 1966. Tetrahedron Lett., : 597–602. Some C-glycosides with antibiotic, antiviral (HIV), and anticancer activities [Google Scholar], [3b] Hori, M., Wakashiro, T., Ito, E., Sawa, T., Takeuchi, T. and Umezawa, H. J. 1968. J. Antibiot., 21A: 264–270. [Chem. Abstr. 1968, 69, 11356j] [Google Scholar], [3c] Farkas, J. and ?orm. 1972. F. Collect. Czech. Chem. Commun., 37: 2798–2803.  [Google Scholar], [3d] Acton, E. M., Ryan, K. J., Henry, D. W. and Goodman, L. 1971. J. Chem. Soc., Chem. Commun., : 986–988.  [Google Scholar], [3e] Nakagawa, Y., Kano, H., Tsukuda, Y. and Koyama, H. 1967. Tetrahedron Lett., : 4105–4109.  [Google Scholar], [3f] Inoue, I. and Kuwaijama, I. 1980. J. Chem. Soc., Chem. Commun., : 251–253.  [Google Scholar], [3g] Buchanan, J. G., Stobie, A. and Wightman, R. H. 1980. ibid., : 916–917. [Crossref] , [Google Scholar], [3h] Hildebrand, S. and Leumann, C. 1996. Angew. Chem., 108: 2100–2102. Angew. Chem. Int. Ed. Engl. 1996, 35, 1968–1970 [Google Scholar]. We want to report on the synthesis of novel 7-substituted isothiazolo = [4,5-d]pyrimidine C-nucleosides. As we could show in previous papers [1] Wamhoff, H., Berressem, R. and Nieger, M. 1994. J. Org. Chem., 59: 1912–1917. Part 2 [Google Scholar], [4] Wamhoff, H., Berressem, R. and Nieger. 1993. M. J. Org. Chem., 58: 5181–5185.  [Google Scholar], there exists a simple approach to the protected C-glycosides 4–6.

     

Oligonucleotides Containing Disaccharide Nucleosides: Synthesis,Physicochemical, and Substrate Properties

Abstract

The efficient synthesis of oligonucleotides containing 2′-O-β-D-ribofuranosyl (and β-D-ribopyranosyl)nucleosides, 2′-O-α-D-arabinofuranosyl (and α-L-arabinofuranosyl)nucleosides, 2′-O-β-D-erythrofuranosylnucleosides, and 2′-O-(5′-amino-5-deoxy-β-D-ribofuranosyl)nucleosides have been developed.     

Redefinition of the hypotrichous ciliate Uncinata,with descriptions of the morphology and phylogeny of three urostylids (Protista,Ciliophora)

We investigated the morphology, morphogenesis and small subunit rRNA gene-based phylogeny of three marine urostylids, Uncinata gigantea Bullington, 1940 Bullington, W. E. (1940). Some ciliates from Tortugas. Papers from the Tortugas Laboratory, 32, 179–221. [Google Scholar], Holosticha heterofoissneri Hu & Song, 2001 Hu, X., & Song, W. (2001). Morphology and morphogenesis of Holosticha heterofoissneri n. sp. from the Yellow Sea, China (Ciliophora, Hypotrichida). Hydrobiologia, 448, 171–179. doi:10.1023/A:1017553406031.[Crossref], [Web of Science ®] , [Google Scholar], and Holosticha cf. heterofoissneri. The dorsal morphogenesis of Uncinata gigantea shows de novo formation of two groups of anlagen near the marginal rows. Holosticha cf. heterofoissneri demonstrates fragmentation of the first dorsal kinety anlage as in Holosticha heterofoissneri. Our population of H. heterofoissneri corresponds well with previously described populations in terms of its general morphology and ciliary pattern. Uncinata gigantea can be recognized by its large and highly contractile body, yellowish to brownish cell colour, two types of cortical granules, and 20–30 transversely oriented and densely arranged cirri in the left marginal row, which often overlie the buccal vertex. Based on the new data, especially infraciliature, the genus Uncinata is here redefined. Both the morphology and phylogenetic analyses suggest that the genus Uncinata should be classified within the family Urostylidae. In addition, both morphological and morphogenetic data suggest that Holosticha bradburyae Gong et al., 2001 Gong, J., Song, W., Hu, X., Ma, H., & Zhu, M. (2001). Morphology and infraciliature of Holosticha bradburyae n. sp. (Ciliophora, Hypotrichida) from the Yellow Sea, China. Hydrobiologia, 464, 63–69. doi:10.1023/A:1013901621439.[Crossref], [Web of Science ®] , [Google Scholar] should be transferred to Uncinata as U. bradburyae (Gong et al., 2001 Gong, J., Song, W., Hu, X., Ma, H., & Zhu, M. (2001). Morphology and infraciliature of Holosticha bradburyae n. sp. (Ciliophora, Hypotrichida) from the Yellow Sea, China. Hydrobiologia, 464, 63–69. doi:10.1023/A:1013901621439.[Crossref], [Web of Science ®] , [Google Scholar]) comb. nov., due to its possession of a characteristically prominent beak-like, leftwards curved projection and the developmental mode of the dorsal kineties. This assignment is supported by the phylogenetic analyses, which placed Uncinata gigantea in a clade with U. bradburyae (Gong et al., 2001 Gong, J., Song, W., Hu, X., Ma, H., & Zhu, M. (2001). Morphology and infraciliature of Holosticha bradburyae n. sp. (Ciliophora, Hypotrichida) from the Yellow Sea, China. Hydrobiologia, 464, 63–69. doi:10.1023/A:1013901621439.[Crossref], [Web of Science ®] , [Google Scholar]) comb. nov., and revealed only 1.13% (19 bp) difference in their SSU-rDNA gene sequence.     

Cooked Odor of Euphausia pacifica Hansen

Quinoxaline and benzimidazole derivatives obtained from L-rhamnose and L-fucose under deoxygenated, weakly acidic, heated conditions were studied using GLC, HPLC, and NMR.

Four quinoxalines and one benzimidazole were obtained from L-rhamnose (RHA-I, II, III, III′, and IV) and L-fucose (FUA-I, II, III, IV, and V) in an acidic solution (MeOH-AcOH-H₂I = 8 : 1 : 2) at 80°C. The total yield of the products as sugar was about 80% from either rhamnose or fucose.

The structure of RHA-I was (2′S)-2-methyl-3-(2′-hydroxypropyl)quinoxaline; RHA-II, (2′R,3′S)-2-(2′,3′-dihydroxybutyl)quinoxaline; RHA-III, (1′S,2′S,3′S)-2-(1′2′3′-trihydroxybutyl)quinoxaline[2-(L-arabino-1′,2′,3′-trihydroxybutyl)quinoxaline]; RHA-III′, 2-(L-ribo-1′,2′,3′-trihydroxybutyl)quinoxaline; and RHA-IV, 2-(L-manno-1′,2′,3′,4′-tetrahydroxypentyl)-benzimidazole, and the structure of FUA-I was the same as RHA-I; FUA-II, (2′S, 3′S)-2-(2′, 3′-dihydroxybutyl)quinoxaline; FUA-III, (1′R, 2′R, 3′S)-2-(1′,2′,3′-trihydroxybutyl)quinoxaline [2-(L-xylo-1′,2′,3′-trihydroxybutyl)quinoxaline; FUA-IV, 2-(L-lyxo-1′,2′,3′-trihydroxybutyl)-quinoxaline; and FUA-V, 2-(L-galacto-1′,2′,3′,4′-tetrahydroxypentyl)benzimidazole. These results suggest no significant difference for the pathways of quinoxaline and benzimidazole formation between L-rhamnose and L-fucose. Possible pathways are proposed for each sugar.     

Synthesis, crystal structure, solution behavior and catalytic activity of a palladium(II)-allyl complex containing a 2-pyridyl-1,2,3-triazole bidentate ligand

The synthesis and characterization of the cationic complex [Pd(η³-C₃H₅)(2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)pyridine)](BF₄) (2) are reported. The solid-state structure of 2 has been unambiguously confirmed by single-crystal X-ray diffraction analysis. ¹H NMR spectroscopy reveals that in solution complex 2 is dynamic and that syn-syn, anti-anti exchange of the allyl protons occurs. Complex 2 exhibits good activity in the Suzuki-Miyaura coupling of aryl bromides with phenyl boronic acid.     

An annotated checklist of Iranian aquatic Polyphaga: Georissidae,Helophoridae, Hydrochidae,Spercheidae, Curculionidae and Erirhinidae (Insecta: Coleoptera)

Abstract

The checklist comprises all species of six families of Iranian aquatic Polyphaga (Coleoptera). In total, 43 species/subspecies within the families, Georissidae (one species), Helophoridae (25 species and two subspecies), Hydrochidae (three species), Spercheidae (one species), Curculionidae (nine species) and Erirhinidae (two species) are listed for the fauna of Iran. Helophorus (Rhopalohelophorus) nanus Sturm, 1836 Sturm, J. (1836), Deulschlands Fauna in Abbildungen nach der Natur mit Beschreibungen. V. Abtheilung. Die Inseclen. Zehntes Bändchen. Käfer, Nürnberg: J. Sturm, 108 pp., pl. 216–227. (also under title: Deutschlands Insecten, Käfer). [Google Scholar] (Helophoridae) is recorded for the first time from Iran. We also present two additional species lists: one with incorrect records (one species) and the other with unidentified species.     

The genera Stegastopsis Kraatz, 1865 and Orostegastopsis Koch, 1962 with description of O. planioculata sp. n. from Oman (Coleoptera: Tenebrionidae: Tentyriini)

The first Asian member of Orostegastopsis Koch, 1962 Koch, C. (1962): Vierter taxonomischer Beitrag zur Kenntnis der Tenebrioniden Somalias: Über die von Prof. G. Scortecci 1953 und 1957 in der Migiurtinia-Provinz gesammelten Arten. 1. Teil. Atti della Società Italiana di Scienze Naturali, 51, 237–270. [Google Scholar] is described and figured: O. planioculata sp. n., which can be easily distinguished from the two Somalian species O. scorteccii Koch, 1962 Koch, C. (1962): Vierter taxonomischer Beitrag zur Kenntnis der Tenebrioniden Somalias: Über die von Prof. G. Scortecci 1953 und 1957 in der Migiurtinia-Provinz gesammelten Arten. 1. Teil. Atti della Società Italiana di Scienze Naturali, 51, 237–270. [Google Scholar] and O. kaszabi (Bremer, 1985 Bremer, H. J. (1985): Eine neue Stegastopsis-Art (Coleopt., Tenebrionidae, Tentyriini) aus Somalia. Entomologische Blätter, 81, 59–61. [Google Scholar]) comb. nov. by the shallow eyes. According to the shape of the clypeus, Stegastopsis kaszabi Bremer, 1985 Bremer, H. J. (1985): Eine neue Stegastopsis-Art (Coleopt., Tenebrionidae, Tentyriini) aus Somalia. Entomologische Blätter, 81, 59–61. [Google Scholar] is transferred from the genus Stegastopsis Kraatz to the genus Orostegastopsis Koch as was already indicated by Bremer (1985 Bremer, H. J. (1985): Eine neue Stegastopsis-Art (Coleopt., Tenebrionidae, Tentyriini) aus Somalia. Entomologische Blätter, 81, 59–61. [Google Scholar]) who treated Orostegastopsis as a subgenus of Stegastopsis: Orostegastopsis kaszabi (Bremer, 1985 Bremer, H. J. (1985): Eine neue Stegastopsis-Art (Coleopt., Tenebrionidae, Tentyriini) aus Somalia. Entomologische Blätter, 81, 59–61. [Google Scholar]) comb. nov. Keys to the species of Stegastopsis and Orostegastopsis are given.     

New records of Hydrochus Leach, 1817 (Coleoptera: Hydrochidae) from Iran

Abstract

Hydrochus ignicollis Motschulsky, 1860 Motschulsky, V. de (1860), ‘Coléoptères rapportés de la Sibérie orientale et notamment des pays situés sur les bords du fleuve Amour par MM. Schrenck, Maack, Ditmar, Voznessenski etc.’, in Reisen und Forschungen im Amur - Lande in den Jahren 1854–1856 im Auftrage der Kaiserl. Akademie der Wissenschaften zu St. Petersburg ausgeführt und in Verbindung mit mehreren Gelehrten herausgegeben. Band II. ed. L. Schrenck , Zweite Lieferung . Coleopteren, St. Petersburg: Eggers und Comp., pp. 80–257, pls. VI–XI. [Google Scholar] is recorded from Iran (Gilan Province) for the first time. In addition, new Iranian provincial records are provided for two species: H. nodulifer Reitter, 1897 Reitter, E . (1897), ‘Dreißig neue Coleopteren aus russisch Asien und der Mongolei’, Deutsche Entomologische Zeitschrift , 1897(2), 209–228. [Google Scholar] (Zanjan Province) and H. farsicus Hidalgo-Galiana, Jäch, and Ribera, 2010 Hidalgo-Galiana, A. , Jäch, M.A. , and Ribera, I . (2010), ‘ Hydrochus farsicus sp. n. from Iran and Notes on other Palearctic Species of the Genus (Coleoptera: Hydrophiloidea: Hydrochidae)’, Zootaxa , 2344, 61–64.[Crossref] , [Google Scholar] (Kohgiluyeh and Boyer-Ahmad Province). Photographs of the habitus, the male genitalia and the habitat of H. ignicollis are provided.     

6-Azathymidine-4′-thionucleosides: synthesis and antiviral evaluation

The synthesis of dideoxy-6-azathymidine 4′-thionucleoside 1-(2,3-dideoxy-4-thio-β-D-erythro-pentofuranosyl)-(6-azathymidine) (2), and the L-nucleoside, 1-(4-thio-β-L-erythro-pentofuranosyl)-(6-azathymidine) (3) and their evaluation against a wide panel of antiviral assays are described. The L-thionucleoside (3) was devoid of antiviral activity. The dideoxy-thionucleoside (2) was moderately active against vaccinia virus (VV) and the herpes simplex virus strains HSV-1 (strain KOS) and HSV-2 (strain G) (MIC 12 μM) and retained inhibitory activity vs a thymidine kinase-deficient strain HSV-1/TK^–, suggesting that (2) is not dependent on viral TK-catalysed phosphorylation for antiviral activity and/or may use an alternative metabolic activation pathway.