共查询到20条相似文献,搜索用时 531 毫秒
1.
《Nucleosides, nucleotides & nucleic acids》2013,32(4-7):901-902
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 (6 and 7) were obtained in 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. 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. 相似文献
2.
Abstract 2′-Deoxy-5′-0-(4,4′-dimethoxytrityl)-5-methyl-N 4-(1-pyrenylmethyl)-α-cytidine (5) was prepared by reaction of 1-pyrenylmethylamine with an appropriate protected 4-(l,2,4-triazolyl)-α-thymidine derivative 3 which was synthesized from 5-O-DMT protected α-thymidine 1. Aminolysis of 3 afforded 3′-O-acetyl-2′-deoxy-5′-O-(4,4′-dimethoxytrityl)-5-methyl-α-cytidine (8). Benzoylation of 8 and removal of acetyl afforded N 4-benzoyl-2-deoxy-5–0-(4,4′-dimethoxytrityl)-5-methyl-α-cytidine (10). The amidites of compounds 5and 10 were prepared and used in α-oligonucleotide synthesis. DNA three-way junction (TWJ) is stabilized when an α-ODN is used for targeting the dangling flanks of the stem in a DNA hairpin. Further stabilization of the TWJ is observed when 5 is inserted into the α-ODN at the junction region. 相似文献
3.
Halise Inci Gul Kaan Kucukoglu Cem Yamali Sinan Bilginer Hafize Yuca Iknur Ozturk 《Journal of enzyme inhibition and medicinal chemistry》2016,31(4):568-573
In this study, 4-(2-substituted hydrazinyl)benzenesulfonamides were synthesized by microwave irradiation and their chemical structures were confirmed by 1H NMR, 13CNMR, and HRMS. Ketones used were: Acetophenone (S1), 4-methylacetophenone (S2), 4-chloroacetophenone (S3), 4-fluoroacetophenone (S4), 4-bromoacetophenone (S5), 4-methoxyacetophenone (S6), 4-nitroacetophenone (S7), 2-acetylthiophene (S8), 2-acetylfuran (S9), 1-indanone (S10), 2-indanone (S11). The compounds S9, S10 and S11 were reported for the first time, while S1–S8 was synthesized by different method than literature reported using microwave irradiation method instead of conventional heating in this study. The inhibitory effects of 4-(2-substituted hydrazinyl)benzenesulfonamide derivatives (S1–S11) against hCA I and II were studied. Cytosolic hCA I and II isoenzymes were potently inhibited by new synthesized sulphonamide derivatives with Kis in the range of 1.79?±?0.22–2.73?±?0.08?nM against hCA I and in the range of 1.72?±?0.58–11.64?±?5.21?nM against hCA II, respectively. 相似文献
4.
N. A. Shakil Manish K. Singh M. Sathiyendiran J. Kumar 《Archives Of Phytopathology And Plant Protection》2013,46(20):1958-1965
Microwave irradiation of 2-hydroxy chalcones under solvent-free conditions resulted in a “green-chemistry” procedure for the preparation of flavanones in good yields, using an unmodified household microwave oven and silica as solid support. By irradiation of 2-hydroxy chalcones with trifluoroacetic acid over silica gel, 11 known flavanones were prepared in high yields. The synthesised compounds were characterised using spectroscopic techniques, namely, 1H NMR, 13C NMR and IR, and screened for their antifungal activity in vitro against Sclerotium rolfsii and Rhizoctonia solani by poisoned food technique. The compounds tested were found to be more active against R. solani, whereas against S. rolfsii, moderate activity was observed, as evident from LC50 values. The most potent compound 2-(4-fluorophenyl)-2,3-dihydrochromen-4-one (4a) had LC50 value of 12.0 mg L?1 followed by 11, 11a, 3a, 9a, 8a, 10a and 10 having LC50 values 18.21, 18.3, 32.9, 50.7, 88.8, 118.8 and 119.7 mg L?1, respectively. 相似文献
5.
《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. 相似文献
6.
Khaled F. Debbabi Hamed M. Al-Saidi Enas H. Aljuhani Shimaa M. Abd El-Gilil 《Journal of enzyme inhibition and medicinal chemistry》2016,31(6):7-19
AbstractThis article describes the synthesis of some novel heterocyclic sulfonamides having biologically active thiophene 3, 4, 5, 6, coumarin 8, benzocoumarin 9, thiazole 7, piperidine 10, pyrrolidine 11, pyrazole 14 and pyridine 12, 13. Starting with 4-(1-(2-(2-cyanoacetyl)hydrazono)ethyl)-N-ethyl-N-methylbenzenesulfonamide (2), which was prepared from condensation of acetophenone derivative 1 with 2-cyanoacetohydrazide. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1H NMR, 13C NMR, 19F NMR and MS spectral data. All the newly synthesized heterocyclic sulfonamides were evaluated as in-vitro anti-breast cancer cell line (MCF7) and as in-vitro antimicrobial agents. Compounds 8, 5 and 11 were more active than MTX reference drug and compounds 12, 7, 4, 14, 5 and 8 were highly potent against Klebsiella pneumonia. Molecular operating environment performed virtual screening using molecular docking studies of the synthesized compounds. The results indicated that some prepared compounds are suitable inhibitor against dihydrofolate reductase (DHFR) enzyme (PDBSD:4DFR) with further modification. 相似文献
7.
E. Charles Kerr E Bruce Eaton L. Thomas Netzel 《Nucleosides, nucleotides & nucleic acids》2013,32(5-6):851-866
Abstract Syntheses of two analogs of deoxyuridine with N,N-dialkylaniline chromophores are reported. 5-[3-(N-methylphenylamino)propanoyl]-2′-deoxyuridine (1) and 5-[2-(4-N,N-dimethylaminophenyl)ethyl)]-2′-deoxyuridine (2) are prepared by palladium-mediated coupling. Preparation of 2 was facilitated by in situ transient O4-trimethylsilyl protection during alkynylation which suppressed secondary cyclization of the coupling adduct. 相似文献
8.
Halise Inci Gul Cem Yamali Fatma Yesilyurt Hiroshi Sakagami Kaan Kucukoglu Ilhami Gulcin 《Journal of enzyme inhibition and medicinal chemistry》2017,32(1):369-374
In this study, 4-[5-(4-hydroxyphenyl)-3-aryl-4,5-dihydro-1H-pyrazol-1-yl]benzenesulfonamide derivatives (8-14) were synthesized for the first time by microwave irradiation and their chemical structures were confirmed by 1H NMR, 13C NMR and HRMS. Cytotoxic activities and inhibitory effects on carbonic anhydrase I and II isoenzymes of the compounds were investigated. The compounds 9 (PSE?=?4.2), 12 (PSE?=?4.1) and 13 (PSE?=?3.9) with the highest potency selectivity expression (PSE) values in cytotoxicity experiments and the compounds 13 (Ki?=?3.73?±?0.91?nM toward hCA I) and 14 (Ki?=?3.85?±?0.57?nM toward hCA II) with the lowest Ki values in CA inhibition studies can be considered as leader compounds for further studies. 相似文献
9.
Krystyna Lesiak Kyoichi A. Watanabe Krzysztof W. Pankiewicz 《Nucleosides, nucleotides & nucleic acids》2013,32(9-11):1857-1860
Abstract 2-(4-Nitrophenylethyl) methylenebis(phosphonate) (1) has been prepared by reaction of 2-(4-nitrophenyl)ethyl alcohol with methylenebis(phosphonyl) tetrachloride. Compound 1 was treated with diisopropylcarbodiimide (DIC) to give bicyclic intermediate 2, which in reaction with suitably protected 2′-deoxynucleosides 3 gave P1,P2-disubstituted methylenebis(phosphonate)s 4. Removal of the nitrophenylethyl group by β-elimination with DBU afforded the corresponding 2′-deoxynucleoside 5′-methylenebis(phosphonate) analogues 5. 相似文献
10.
Sergey N. Mikhailov Ekaterina V. Efimtseva Sergey V. Meshkov Earl R. Kern 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):615-623
Abstract New nucleoside analogues on the basis of 4(R), 5(R)-dihydroxymethy1-2-methyl-1,3-dioxoiane have been prepared. Alkylation of thymine, adenine and N2 -palmitoyl-guanine with 2-bromomethyl-4(R),5(R)-dibenzyloxymethyl-1,3-dioxolane followed by separation of regio isomers by adsorption chromatography and deprotection yielded the desired chiral nucleoside analogues. The structures of thus prepared compounds were confirmed by UV and PMR spectroscopy. The obtained compounds 11 have no anti-HIV and ant i herpetic activity and are not cytotoxic. 相似文献
11.
E. S. H. El Ashry A. A. Kassem H. Abdel-Hamid F. F. Louis Sh. A. N. Khattab M. R. Aouad 《Nucleosides, nucleotides & nucleic acids》2013,32(5):437-451
Regioselective alkylation of 5-(3-chlorobenzo[b]thien-2-yl)-4H-1,2,4-triazole (1) with hydroxy alkylating agents 2, 3, 13, and the 2,3-O-isopropylidene-1-O-(p-tolylsulfonyl)-glycerol (10) afforded the corresponding S-alkylated derivatives 6, 7, 11, and 14 under both conventional and microwave irradiation conditions; bentonite as a solid support gave better results, with no change in regioselectivity. A facile intramolecular dehydrative ring closure of 6, 7, 11, and 14 using K2CO3 in DMF afforded the corresponding fused triazolo-thiazines and thiazolo-triazole 17–19. The isopropylidenes and acetyl derivatives of the products were prepared. 相似文献
12.
H. A. El-Sayed A. H. Moustafa A. Z. Haikal I. M. Abdou E. S. H. El-Ashry 《Nucleosides, nucleotides & nucleic acids》2013,32(9):1061-1071
Reaction of ethyl 4-thioxo-3,4-dihydropyrimidine-5-carboxylate derivatives 1a,b and ethyl 4-oxo-3,4-dihydropyrimidine-5-carboxylate 1c with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide in KOH or TEA afforded ethyl 2-aryl-4-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosylthio or/ oxy)-6-methylpyrimidine-5-carboxylate 6a-c. The glucosides 6a and 6b were obtained by the reaction of 1a and 1b with peracetylated glucose3 under MW irradiation. Mercuration of 1a followed by reaction with acetobromoglucose gave the same product 6a. The reaction of 1a-c with peracetylated ribose 4 under MW irradiation gave ethyl 2-aryl-4-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosylthio)-6-methylpyrimidine-5-carboxylate 8a–c. The deprotection of 6a–c and 8a–c in the presence of methanol and TEA/H2O afforded the deprotected products 7a–c and 9a–c. The structure were confirmed by using 1H and 13CNMR spectra. Selected members of these compounds were screened for antimicrobial activity. 相似文献
13.
Daniel E. Morrison Fatiah Issa Mohan Bhadbhade Ludwig Groebler Paul K. Witting Michael Kassiou Peter J. Rutledge Louis M. Rendina 《Journal of biological inorganic chemistry》2010,15(8):1305-1318
The preparation of boronated triaryl and tetraaryl phosphonium salts of the type [PPh3CH2R]Br [R is 4-boronophenyl (1), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)phenyl (2), 3-boronophenyl (3), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)phenyl (4), 2-boronophenyl (5), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)phenyl (6), and closo-1,2-carboran-1-yl (7)] is described. These compounds were prepared by the reaction of triphenylphosphine with benzylic bromides or 1-bromomethyl-closo-1,2-carborane in acetonitrile solution at 85 °C. The zwitterionic nido-7,8-carborane derivative PPh3CH2C2B9H11 (8) was prepared by treatment of 7 with cesium fluoride in refluxing ethanol. All compounds were fully characterized by multinuclear (1H, 11B, 13C, and 31P) 1D- and 2D-NMR spectroscopy, electrospray ionization mass spectrometry, and elemental analysis, and single-crystal X-ray
structures were determined for compounds 1, 3, 7, and 8. The cytotoxicities and boron uptake of selected derivatives were investigated in vitro using human glioblastoma (T98G) and
canine kidney tubule (MDCK II) cells. The zwitterionic species 8 was found to be the least cytotoxic agent while also delivering the greatest amount of boron to the T98G cells, peaking at
9.15 ± 2.65 μg B/mg protein. 相似文献
14.
《Nucleosides, nucleotides & nucleic acids》2013,32(9):1735-1750
A series of 3-alkyl-5-((Z))-arylidene-2-thiohydantoins 4a-l were synthesized from the direct condensation of the aromatic aldehydes with 3-alkyl-2-thiohydantoins 3a-c, which in turn were prepared from the reaction of glycine (1) and alkyl isothiocyanates 2a-c. The alkylation of 4a-l with methylthioethyl chloride gave 5-((Z))-arylidene-3-alkyl-S-(2-methylthioethyl)-2-thiohydantoins 5a-e. S-Glucosylation took place on the reaction of 4a-l with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide under anhydrous alkaline conditions. These structures have been confirmed from a model study of the coupling of 4a with methylthioethyl chloride and α-D-glucose pentaacetate, respectively under Lewis acid conditions. 相似文献
15.
Zhi-Xian Wang Weili Duan Leonard I. Wiebe Erik De Clercq Jan Balzarini Edward E. Knaus 《Nucleosides, nucleotides & nucleic acids》2013,32(9):1397-1411
Abstract A group of 1-[(2-hydroxyethoxy)methyl]- (12) and 1-[(1,3-dihydroxy-2-propoxy)methyl]- (13) derivatives of 2,4-difluorobenzene possessing a variety of C-5 substituents (R = Me, H, I, NO2) were designed with the expectation that they may serve as acyclic 5-substituted-2′-deoxyuridine (thymidine) mimics. Compounds 12 and 13 (R = Me, H, I) were inactive as anticancer agents (C50 = 10?3 to 10?4 M range), whereas the 5-nitro compounds (12d, 13d) exhibited weak-to-moderate cytotoxicity (CC50 = 10?5 to 10?6 M range) against a variety of cancer cell lines. All compounds prepared (12a-d, 13a-d) were inactive as antiviral agents in a broad-spectrum antiviral screen that also included the human immunodeficiency virus (HIV-1 and HIV-2) and herpes simplex virus (HSV-1 and HSV-2). 相似文献
16.
《Journal of enzyme inhibition and medicinal chemistry》2013,28(4):561-568
A series of 2-{4-[4-(2,5-disubstituted thiazolyl)phenylethyl] piperazin-1-yl}-1,8-naphthyridine-3-carbonitriles were synthesized in an effort to prepare novel atypical antipsychotic agents. The compounds were synthesized either by microwave irradiation technique or by conventional synthesis and were characterized by spectral data (IR, 1H NMR, and MS) and the purity was ascertained by microanalysis. The D2 and 5-HT2A affinity of the synthesized compounds was screened in vitro by radioligand displacement assays on membrane homogenates isolated from rat striatum and rat cortex, respectively. Furthermore, all the synthesized compounds were screened for their in vivo pharmacological activity in Swiss albino mice. The D2 antagonism studies were performed using climbing mouse assay model and 5-HT2A antagonism studies were performed using quipazine-induced head twitches in mice. It was observed that none of the new chemical entities exhibited catalepsy and 10f is the most active among the synthesized compounds with 5-HT2A/D2 ratio of 1.1286 although the standard drug risperidone exhibited 5-HT2A/D2 ratio of 1.0989. 相似文献
17.
《Nucleosides, nucleotides & nucleic acids》2013,32(9):1655-1670
The target compounds 5-[N-(6-amino-hexyl)-acrylamide]-2′,3′-didehydro-2′,3′-dideoxy-uridine (12) and 5-{N-[5-(methoxycarbonyl)-pentyl]-acrylamide}-2′,3′-didehydro-2′,3′-dideoxy-uridine (15) were prepared by the palladium acetate-triphenylphosphine-catalyzed reaction of the 5′-O-acetyl-5-iodo-d4T analogue (3). These compounds 12 and 15 can be used to prepare nucleotide probes carrying fluorescent labels and were nevertheless screened for their anti-HIV activity. The biological data demonstrated that none of them were active against HIV-1. 相似文献
18.
《Journal of enzyme inhibition and medicinal chemistry》2013,28(4):485-491
A series of 4-thiazolidinones bearing a sulfonamide group (4a–w) were prepared by cyclizing various 5-bromo-2-methoxy-N’-[(1E)-arylmethylene/arylethylidene]benzenesulfonohydrazides. All the compounds were characterized by IR, 1H NMR, and elemental analysis. The compounds were tested for their anticonvulsant activity utilizing MES and scPTZ animal models. The majority of the compounds exhibited significant activity against both animal models; however, compounds 4c, 4m, and 4o displayed promising activity and could be considered as leads for further investigations. 相似文献
19.
《Journal of enzyme inhibition and medicinal chemistry》2013,28(5):944-953
A new series of four biologically active triazole derived Schiff base ligands (L1–L4) and their cobalt(II), nickel(II), copper(II) and zinc(II) complexes (1–16) have been synthesized and characterized. The ligands were prepared by the condensation reaction of 3-amino-5-methylthio-1H-1,2,4-triazole with chloro-, bromo- and nitro-substituted 2-hydroxybenzaldehyde in an equimolar ratio. The antibacterial and antifungal bioactivity data showed the metal(II) complexes to be more potent antibacterial and antifungal than the parent Schiff bases against one or more bacterial and fungal species. 相似文献
20.
SYNTHESIS AND STRUCTURE DETERMINATION OF SOME OXADIAZOLE-2-THIONE AND TRIAZOLE-3-THIONE GALACTOSIDES
《Nucleosides, nucleotides & nucleic acids》2013,32(9):1671-1682
The syntheses of 5-pyridyl-3((β-D-galactopyranosyl)-1,3,4-oxadiazole-2-thiones 3a–3c and 5-pyridyl-2((β-D-galactopyranosyl)-4-benzyl-1,2,4-triazole-3-thiones 6a–6c are reported. The existence of N-galactosides – not S-galactosides – was proven by IR and 15N NMR spectroscopy. The structures of the final products and the intermediates were elucidated by IR, 1H, 13C and 15N NMR spectroscopy and mass spectrometry. 相似文献