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1.
Julia Castro-pichel Ma. Teresa García-López Rosario Herranz Concepción Pérez 《Nucleosides, nucleotides & nucleic acids》2013,32(7):985-1000
Abstract 5′-O-[N-(Aminoacyl)sulfamoyl]-uridines and -thymidines 4a-12a and 4b-12b have been synthesized and tested against Herpes Simplex virus type 2 (HSV-2) and as cytostatics. Condensation of 2′,3′-O-isopropylidene-5′-O-sulfamoyluridine and 3′-O-acetyl-5′-O-sulfamoylthymidine with the N-hydroxysuccinimide esters of Boc-L-Ser(Bzl), (2R, 3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbuta-noic acid [(2R, 3S-N-Z-AHPBA], (2R, 3S) and (2S, 3R)-N-Boc-AHPBA gave 4a,b-7a,b, which after removal of the protecting groups provided 1Oa,b-12a,b. A study of the selective removal of the O-Bzl protecting group from the L-Ser derivatives 4a,b, without hydrogenation of the pyrimidine ring, has been carried out. Only the fully protected uridine derivatives 4a-7a did exhibit high anti-HSV-2 activity, and none of the synthesized compounds showed significant cytostatic activity against HeLa cells cultures. 相似文献
2.
J. Fuentes Mota P. Areces Bravo F. Rebolledo Vicente J. I. Fernández García-Hierro J. A. Galbis Pérez 《Nucleosides, nucleotides & nucleic acids》2013,32(2):115-121
Abstract Acid catalyzed isomerization of 1-aryl-(1,2-dideoxy-D-glycero-β-L-gluco-heptofuranose) [1,2-d]-2-imidazolines (4) yields 1-aryl-4-(D-galacto-pentitol-1-yl)imidazoles (8) which can be also obtained by reductive desulphuration of 1-aryl-2-benzylthio-4-(D-galacto-pentitol-1-yl)imidazoles (6). Compounds (4) were obtained by desulphuration with Raney nickel from 1-aryl-(1,2-dideoxy-D-glycero-β-L-gluco-heptofuranose) [1,2-d]-imidazolidine-2-thiones (1) or 1-aryl-2-benzylthio-(1,2-dideoxy-D-glycero-β-L-gluco-heptofuranose) [1,2-d]-2-imidazolines (2). 相似文献
3.
《Journal of Russian & East European Psychology》2013,51(4):13-22
The problem of the correlation of the electrical activity of various parts of the brain is closely linked with the problem of the functional connections between them. The investigation of such relationships using an index of synchronization of the alpha- or beta-rhythm in a human EEG based on calculations of the coincidence of the phases of oscillations for definite short periods of time has been carried out in a number of studies (Adrian and Yamagiwa [9], Cohn [16], Goodwin and Stein [19], Darrow et al. [17], Garoutte and Aird [18], Adamovich [1]). These investigations revealed a high degree of synchrony at symmetrical points of both hemispheres and a phase lag of alpha-waves in the frontal sections compared to the occipital. In recent years M. N. Livanov et al. [2, 6, 7] have been studying the synchronization of electrical activity of various areas of the cortex of the large hemispheres in man by means of encephaloscopy and subsequent data analysis on electronic computers. They have shown that the degree of synchronization of the EEG of the different sections of the cerebral cortex normally found in man varies significantly and changes under the influence of functional load and pharmacological tests. 相似文献
4.
Jack D. Anderson Roland K. Robins Ganapathi R. Revankar 《Nucleosides, nucleotides & nucleic acids》2013,32(5):853-863
Abstract The synthesis of pyrazolo[3,4-d]pyrimidine ribonucleoside 3′, 5′-cyclic phosphates related to cAMP, cIMP and cGMP has been achieved for the first time. Phosphorylation of 4-amino-6-methylthio-1-β-D-ribo-furanosylpyrazolo[3,4-d]pyrimidine (1) with POCl3 in trimethyl phosphate gave the corresponding 5′-phosphate (2a). DCC mediated intramolecular cyclization of 2a gave the corresponding 3′, 5′-cyclic phosphate (3a), which on subsequent dethiation provided the cAMP analog 4-amino-1-β-D-ribofuranosylpyrazolo[3, 4-d]pyrimidine 3′, 5′-cyclic phosphate (3b). A similar phosphorylation of 6-methylthio-1-β-D-ribofuranosylpyrazolo[3, 4-d]pyrimidin-4(5H)-one (5), followed by cyclization with DCC gave the 3′, 5′-cyclic phosphate of 5 (9a). Dethiation of 9a with Raney nickel gave the cIMP analog 1-β-D-ribofuranosylpyrazolo[3, 4-d]pyrimidin-4(5H)-one 3′, 5′-cyclic phosphate (9b). Oxidation of 9a with m-chloroperoxy benzoic acid, followed by ammonolysis provided the cGMP analog 6-amino-1-β-D-ribofuranosylpyrazolo [3, 4-d] pyrimidin-4(5H)-one 3′, 5′-cyclic phosphate (7). The structural assignment of these cyclic nucleotides was made by UV and H NMR spectroscopic studies. 相似文献
5.
Mohammed A. E. Sallam 《Nucleosides, nucleotides & nucleic acids》2013,32(3):297-313
Abstract The C-nucleoside analogs 6,7-dimethyl-3-β-D-erythrofuranosyl-1-phenylpyrazolo[3,4-b]quinoxaline 4 and 3-β- D -erythrofuranosyl-1-p-fluorophenylpyrazolo[3,4-b]quinoxaline 8 were prepared by dehydration of the polyhydroxyalkyl chain of 6,7-dimethyl-1-phenyl-3-( D -arabino-tetritol-1-yl)-pyrazolo[3,4-b]quinoxaline 3 and 1-p-fluorophenyl-3-( D -arabino-tetritol-1-yl)-pyrazolo[3,4-b]quinoxaline 7, respectively. The structure and anomeric configuration of the products were determined by n.m.r. spectroscopy. The mass spectra and biological activities in connection with chemical constitution are discussed. 相似文献
6.
Tai-Shun Lin Shi-Ping Xu Mao-Chin Liu William R. Mancini 《Nucleosides, nucleotides & nucleic acids》2013,32(4):559-568
Abstract Optically pure (R)- and (S)-1-[[2-hydroxy-1-(aminomethyl) ethoxy]methyl]-5-benzyluracil [(R)-AHPBU and (S)-AHPBU, respectively], two potent uridine phosphorylase inhibitors, have been synthesized via multi-step syntheses starting from independent chiral compounds. The activity of (R)-AHPBU, (S)-AHPBU, and (R,S-AHPBU which have been previously synthesized, on the inhibition of uridine phosphorylase from Sarcoma-180 cells has been studied and compared. The K. values for (R,S)-, (R)- and (S)-AHPBU were determined to be 15·2.3, 17·2.7 and 16·2.0 nM, respectively. This indicates that (R) and (S) optical enantiomers have the same affinity for binding to uridine phosphorylase. These acyclic pyrimidine amino nucleoside analogues represent a new class of potent uridine phosphorylase inhibitors, which has a bulky hydrophobic substituent at the 5-position in the uracil base, yet has remarkably high water solubility. 相似文献
7.
Steven G. Wood N. Kent Dalley Rose D. George Roland K. Robins Ganapathi R. Revankar 《Nucleosides, nucleotides & nucleic acids》2013,32(2):187-194
Abstract The first chemical synthesis of 3-amino-1-β-D-ribofuranosyl-s-triazolo[5,1-c]-s-triazole (6) is described. Direct glycosylation of 3-amino-5(7)H-s-triazolo[5,1-c]-s-triazole (2) with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (3) in the presence of TMS-triflate gave 3-amino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-s-triazolo[5, 1-c]-s-triazole (4) which, on ammonolysis, gave 6. The absolute structure of 6 is determined by X-ray diffraction techniques employing Mo Kα radiation. The structure is solved by direct methods and refined to the R value of 0.044 by using a full-matrix least-squares method. The sugar of 6 has a 3T2 configuration. The torsion angles about the C5′–C4′ bond are both gauche and the torsion angle about the glycosidic bond is in the anti range. Each azole ring of the aglycon is planar and the dihedral angle between the planes of the rings is 3.6°. 相似文献
8.
B. Azmy P. Fernández-resa P. Goya R. Nieves C. Ochoa M. Stud 《Nucleosides, nucleotides & nucleic acids》2013,32(4):325-337
Abstract Synthesis of methyl, glucosyl and ribosyl derivatives of 7-amino-2H, 4H-[1, 2, 3]triazolo [4, 5-c] [1, 2, 6] thiadiazine 5, 5-dioxide (1a) and 7-amino-4H- [1, 2, 5] thiadiazolo [3, 4-c][1, 2, 6] thiadiazine 5, 5-dioxide (2a) is described. The structures of the glycosyl derivatives are discussed on the basis of their PMR- and UV-spectroscopic data. 相似文献
9.
Najim A. Al-Masoudi Wolfgang Pfleiderer Wasfi A. Al-Masoudi 《Nucleosides, nucleotides & nucleic acids》2013,32(7):675-685
Abstract Reactjon of (2-acetoxyethoxy)methyl bromide with the silylated lumazine bases (1-6) in the presence of n-Bu4NI leads to the formation of the nucleosides 8, 10, 12, 14, 16 and 18 respectively. Deacetylation with methanolic ammonia afforded the free nucleosides 9, 11, 13, 15, 17 and 19, respectively, in good yields. Structural proofs of the newly synthesized compounds are based on elemental analyses, UV and 1H-NMR spactra. None of the acyclic nucleosides exhibited antiviral activity against HSV-1 in vitro. 相似文献
10.
Abstract Three new appropriately protected phosphoramidites have been synthesized. Two of them (1 and 2) are isosteric to that of inosine (3) [1], one is a derivative of 1′3-propanediol (4). Whereas the inosine isosteres contain an ambiguous base recognizing adenine, guanine as well as cytosine residues in double stranded DNA-fragments the 1,3-propanediol unit can be seen as a simple nucleoside substitute in a DNA chain. It contains only those structural elements necessary to form the sugar/phosphate backbone, without supplying the DNA with either a base [21 or a 2′-deoxyribofuranosyl moiety. 相似文献
11.
Kandasamy Ramasamy Roland K. Robins Ganapathi R. Revankar 《Nucleosides, nucleotides & nucleic acids》2013,32(3):385-392
Abstract A synthesis of 2,4-dideazaribavirin ( 2 ), brunfelsamidine ribonucleoside ( 8c ) and certain related derivatives are described for the first time using the stereospecific sodium salt glycosylation procedure. Glycosylation of the sodium salt of pyrrole-3-carbonitrile ( 4 ) with 1-chloro-2, 3-O-t-isopropylidene-5-O-t-butyldimethylsilyl-α-D-ribofuranose ( 5 ) gave exclusively the corresponding blocked nucleoside ( 6 ) with β-anomeric configuration, which on deprotection provided 1-β-D-ribofuranosylpyrrole-3-carbonitrile ( 7 ). Functional group tranformation of 7 gave 2 , 8c and related 3-substituted pyrrole ribonucleosides. These compounds are devoid of any significant antiviral/antitumor activity invitro. 相似文献
12.
《Journal of Russian & East European Psychology》2013,51(3-4):90-94
It is well known to all those acquainted with D. N. Uznadze's theory of set [ustanovka] (1) that this theory was meant to answer the question of "the character and inner structure of human activity" [11; 79]. But, as A. T. Bochorishvili correctly noted, we do not yet have "clarity in basic concepts. … Soviet psychology cannot yet go so far as to speak of the content of the basic concept of the psychology of set, of the content of set itself" [5: 15]. As a panacea for overcoming these differences of opinion, Bochorishvili proposes that we "widely and actively develop investigations of the theoretical bases of the psychology of set as D. N. Uznadze understood if" (ibid.). 相似文献
13.
James L. Kelley James A. Linn Lilia Beauchamp Peter Collins J. W. T. Selway Karen K. Biron 《Nucleosides, nucleotides & nucleic acids》2013,32(4):475-489
Abstract The synthesis and antiherpetic activity of 9-[[[2-hydroxy-1-(hydroxymethyl)ethyl]thio]methy1]guanine (4) and 1-[[[2-hydroxy-1-(hydroxymethyl)ethyl]thio]methy]cytosine (6), the side-chain thio analogues of ganciclovir (3) and BW A1117U (5), are described. The sidechain synthon 1,3-bis(benzyloxy)-2-[(chloromethyl)thio]propane (11) was prepared in four steps from 1,3-bis(benzyloxy)-2-propanol (7). Alkylation of 2-amino-6-chloro-9H-purine with 11 provided the intermediate 9-substituted-2-amino-6-chloropurine 12, which was conveniently converted to 4 in two steps. Reaction of a fivefold excess of cytosine with 11 provided the desired 1-isomer 14, which was debenzylated to give 6. In contrast with ganciclovir (3) and BW A1117U (5), neither 4 nor 6 had significant in vitro activity against human cytomegalovirus. 相似文献
14.
Abdullah Hijazi 《Nucleosides, nucleotides & nucleic acids》2013,32(5):529-537
Abstract The fusion reaction between 2-trifluoromethylnaphth[2,3-d]imidazole (1) and 1-0-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (2) leads to 2,3′,5′-tri-O-benzoyl-1-β-D-ribofuranosylnaphth[2,3-d]imidazole (3). Debenzoylation of (3) gives the corresponding nucleoside 1-β-D-ribofuranosyl -2-trifluoromethylnaphth[2,3-d]imidazole (4). Structural proofs are based on elementary analysis, UV-and 1H-NMR spectra. 相似文献
15.
Jiří žemlička 《Nucleosides, nucleotides & nucleic acids》2013,32(3):245-264
Abstract New analogues of antiviral agents 9-(2, 3-dihy-droxyproply) adenine (DHPA, 1a.) and 9-(2-hydroxyethoxymethyl) guanine (acyclovir, Ib) - compounds Ic and Id were prepared and their biological activity was investigated. Racemic 1, 2, 4-butanetriol (2) was converted to the corresponding benzylidene derivative (3a) by acetalation with benzalde-hyde and triethyl orthoformate. Acetal 3a and p-toluene- sul-fonyl chloride in pyridine gave the corresponding p-toluenes fonate 3b. Alkylation of adenine 5a via sodium salt of 5a with 3b in dimethylformamide or in the presence of tetra-n-butylammonium fluoride in tetrahydrofuran gave intermediate 6a. Reaction of 2-amino-6-chloropurine (5b) with 3b effected by K2CO3 in dimethylsulfoxide gave compound 6b and a smaller amount of 7-alkylated proauct 7. A similar transformation catalyzed by tetra-n-butylammonium fluoride afforded only intermediate 5b. Acid-catalyzed de-protection (hydrolysis) of 6b and 6a gave the title compounds Ic and Id. The S-enantiomer of Ic was deaminated with adenosine deaminase. Our results argue against the presence of a methyl group-binding site of adenosine deaminase. Compounds Ic and Id exhibited little or no activity in antiviral assays with several DNA and RNA viruses. 相似文献
16.
M. Bueno Martínez E. Román Galán J. A. Galbis Pérez 《Nucleosides, nucleotides & nucleic acids》2013,32(2):227-244
Abstract Fusion of 2-trimethylsilylpyridine and tetra-O-acetyl-aldehydo-D-xylose or 2,3:4,5-di-O-isopropylidene-aldehydo-L-arabinose led, after removing of the protecting groups, to 2-(pentitol-1-yl)pyridines of D-gulo and D-ido or L-manno configurations. Dehydration of the sugar-chain with D-gulo and D-ido configurations gave the corresponding 2′,5′-anhydro derivatives, whereas 2-(5-O-isopropyl-L-manno-pentitol-1-yl)-pyridine was the only compound formed by dehydration of the sugar-chain with L-manno configuration. Structural proofs are based on 1H and 13C NMR spectra. 相似文献
17.
Bozenna Golankiewicz Joanna Zeidler Erik De Clercq 《Nucleosides, nucleotides & nucleic acids》2013,32(4):663-678
Abstract C-acyclic nucleoside analogues of inosine and guanosine 8-[(RS)-2,3-dihydroxypropyl] imidazo [1,5-a]-1,3,5-triazin-4 (3H)-ones 6a, c, d were synthesized. The route involved the cyclization-rearrangement of 5-acylamino-5-allyl-6-amino-4,5-dihydropyrimidin-4-ones 4a-c to 8-allylimidazo [1,5-a]-1,3,5-triazin-4 (3H) ones 5a-c. 5a was transformed selectively into 5d by reductive desulfurization with highly deactivated Raney nickel. The poorly soluble compounds 5b and 5c were converted to N-2-acetylated 5f and 5g. Osmium tetroxide hydroxylation of 5d, f, g gave 6a, c, d. None of the newly synthesized C-acyclic nucleoside derivatives showed an appreciable antiviral or antitumor cell activity. 相似文献
18.
Tomokazu Sugawara Toyoaki Ishikura Tokuo Itoh Yoshihisa Mizuno 《Nucleosides, nucleotides & nucleic acids》2013,32(3):239-251
Abstract 9-β-D-Arabinofuranosyldeazaadenines [1-deaza-araA (4a) and 3-deaza-araA (4b)] were prepared from 6-chloro-β-D-ribofuranosyl-1- (6a) and -3-deazapurine (6b), respectively. Synthesis of 2′-deoxy-1-deaza-adenosine (5a) from 1-deazaadenosine (6c) is also described. 相似文献
19.
Abstract The fusion reaction between 1-trimethylsilyl-naphth[2,3-d]imidazole (3) and its 2-methyl derivative (4) with 2, 3, 5-tri-O-benzoyl-1-bromo-D-ribofuranose (6) leads to anomeric mixtures of the corresponding 2', 3', 5'-tri-O-benzoyl-1α- and β-D-ribofuranosylnaphth[2,3-d]imidazoles (7, 11 and 13). Separation of the anomers was achieved by chromatographical means and debenzoylation yielded the corresponding nucleosides (8, 12 and 10, 14). Structural proofs are based on elementary analysis, UV- and 1H-NMR spectra. 相似文献
20.
Naeem B. Hanna Krishna G. Upadhya Charles R. Petrie Roland K. Robins Ganapathi R. Revankar 《Nucleosides, nucleotides & nucleic acids》2013,32(4):343-362
Abstract The synthesis of several 5′-substituted derivatives of ribavirin (1) and tiazofurin (3) are described. Direct acylation of 1 with the appropriate acyl chloride in pyridine-DMF gave the corresponding 5′-O-acyl derivatives (4a-h). Tosylation of the 2′, 3′-O-isopropylidene-ribavirin (6) and tiazofurin (11) with p-toluenesulfonyl chloride gave the respective 5′-O-p-tolylsulfonyl derivatives (7a and 12a), which were converted to 5′-azido-5′-deoxy derivatives (7b and 12b) by reacting with sodium/lithium azide. Deisopropylidenation of 7b and 12b, followed by catalytic hydrogenation afforded 1-(5-amino-5-deoxy-β-D)-ribofuranosyl)-1, 2, 4-triazole-3-carboxamide (10b) and 2 - (5 -amino- 5-deoxy- β-D-ribofuranosyl) thiazole-4-carboxamide (16), respectively. Treatment of 6 with phthalimide in the presence of triphenylphosphine and diethyl azodicarboxylate furnished the corresponding 5′-deoxy-5′-phthaloylamino derivative (9). Reaction of 9 with n-butylamine and subsequent deisopropylidenation provided yet another route to 10b. Selective 5′-thioacetylation of 6 and 11 with thiolacetic acid, followed by saponification and deisopropylidenation afforded 5′-deoxy-5′-thio derivatives of 1-β-D-ribofuranosyl-1, 2, 4-triazole-3-carboxamide (8a) and 2-β-D-ribofuranosylthiazole-4-carboxamide (15), respectively. 相似文献