共查询到20条相似文献,搜索用时 15 毫秒
1.
Maqbool A. Siddiqui Harry Ford Jr. Clifford George Victor E. Marquez 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):235-250
Abstract A new chiral synthesis of the pseudosugar synthon (1R,2S,4R,5S)-1-[(benzyloxy)methyl]-2-tert-butyloxy-4-hydroxybicyclo[3.1.0]hexane (12) is reported. This compound was used as a template for the construction of carbocyclic nucleoside 4, a conformationally rigid analogue of 2′-deoxyaristeromycin. The X-ray structure and 1H NMR analysis confirmed the exclusive North [2′-exo (2E)] conformation of 4 which is vastly different from that of other non-rigid carbocyclic nucleosides. Compound 4 showed good in vitro antiviral activity against human cytomegalovirus and EBV with minimal cytotoxicity. 相似文献
2.
Tamer Nasr Yosuke Taniguchi Tomoko Takaki Hidenori Okamura Shigeki Sasaki 《Nucleosides, nucleotides & nucleic acids》2013,32(12):841-860
(1S,3S,4R)-1-Phenyl-1-thymidyl-3-hydroxy-4-hydroxymethylcyclopentane (10) and their analogs were synthesized, incorporated into the oligodeoxynucleotides, and their properties were evaluated for the formation of duplex and triplex DNA. The known chiral cyclopentanone derivative was converted into the corresponding ketimine sulfonamide derivative, which was subjected to a stereoselective PhLi addition. The formed sulfonamide was hydrolyzed to afford the primary amino group, on which the thymine moiety was built. The benzyl protecting groups were removed to form the nucleoside analog having a phenyl group and the thymine unit at the 1′ position of a carbocyclic skeleton (10). In the estimation of the oligodeoxynucleotides incorporating 10 for duplex and triplex formation, the carbocyclic nucleoside analog 10 did not show the stabilizing effect for duplex formation; on the other hand, it stabilized the triplex. Therefore, the skeleton of the phenyl-substituted carbocyclic nucleoside analog 10 may be a platform for the formation of stable triplex DNA. 相似文献
3.
James W. Leahy Stewart W. Schneller 《Nucleosides, nucleotides & nucleic acids》2013,32(5-6):1081-1082
Abstract The synthesis of the carbocyclic derivative of lin-benzo-2′,3′-dideoxyinosine has been accomplished as an example of a benzo-separated carbocyclic purine analogue. 相似文献
4.
Abstract The synthesis of (-)-3-[(1S,2S,3R,4R)-2,3-dihydroxy-4-(hydroxmethyl) cyclopentan-1-yl]-1H-pyrazolo[4,3-c]pyridme-4,6(5H,7H)-dione 3 was accomplished via enantiomerically pure carbocyclic 5-(β-D-ribofuranosyl)tetrazole 4. 相似文献
5.
M. Escobar F. Fernández X. García-Mera J. E. Rodriguez-Borges 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):625-626
Abstract Aminoalcohol precursor of carbocyclic analogues of nucleosides (±)-cis-3-aminomethyl-1-indanylmethanol was efficiently synthesized starting from benzonorbornadiene (5) previously prepared by addition of cyclopentadiene to 1-bromo-2-fluorobenzene. 相似文献
6.
Abstract The synthesis of carbocyclic nucleosides, cis-9-[4-(1,2-dihydroxyethyl)-cyclopent-2-enyl]guanine (3) and cis-2-amino-6-cyclopropylamino-9-[4-(1,2-dihydroxyethyl)-cyclopent-2-enyl]guanine (4), was achieved from cyclopentadiene (5) in five and six steps, respectively. This route involves a hetero Diels-Alder reaction and a Pd(0)-catalyzed coupling reaction. 相似文献
7.
Vishnumurthy R. Hegde Katherine L. Seley Xing Chen Stewart W. Schneller 《Nucleosides, nucleotides & nucleic acids》2013,32(8):1905-1910
Abstract The chiral synthesis of (1S,3S,4S)-1-(3,4-dihydroxycyclopent-1-yl)-1H?thymine (carbocyclic 5′-nor thymidine, 4) has been achieved in 5 steps from (+)-(lR,4S)-4-hydroxy-2-cyclopenten-1-yl acetate (5) and N3?benzoylthymine. Compound 4 is viewed as a monomeric building block for poly-T-like oligomers. 相似文献
8.
M. Isabel Nieto J. Manuel Blanco Olga Caamaño Franco Fernández Xerardo Garcia-mera Carmen Lopez 《Nucleosides, nucleotides & nucleic acids》2013,32(10):2253-2263
Abstract Six new carbocyclic nucleosides were prepared by mounting a purine (compounds 4–6), 8-azapurine (7 and 8) or undine (9) base on the ammo group of (1S,3R)-3-amino-2,2,3-trimethylcyclopentylmethanol (10). At subtoxic concentrations, compounds 5-9 showed at best marginal antiviral activity. 相似文献
9.
Tokumi Maruyama Yasuaki Hanai Yoshiko Sato 《Nucleosides, nucleotides & nucleic acids》2013,32(2-4):855-864
Abstract 9-Cyclobutyladenines bearing both methylene and hydroxymethyl groups, 3 and 4, were prepared by dehydration of carbocyclic oxetanocin A (1a). Introduction of a double bond into cyclobutane ring was achieved by allylic oxidation of N 6-benzoyl-9-[3-methylenecyclobutyl]adenine (12), which after several steps, afforded 9-[3-(hydroxy-methyl)-2-cyclobutenyl)adenine (5). 相似文献
10.
L. A. Agrofoglio F. Girard C. Demaison M-G. Lee P. Roingeard A. Fridland 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):601-602
Abstract The synthesis of several optically pure carbocyclic α-L-isomeric homonucleosides [3a-e, 6a,b, 7a,b, 10a-d] is reported. The (1R, 5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one 1 was used as a chiral starting material. 相似文献
11.
Ramakrishnamraju Samunuri 《Nucleosides, nucleotides & nucleic acids》2019,38(6):391-399
The need of long-term treatment for chronic HBV, emergence of drug-resistant viruses and inefficiency of currently approved therapies to eliminate covalently closed circular DNA (cccDNA), mandates identification of potent and selective inhibitors of HBV replication with novel mechanisms of action. Entecavir, a carbocyclic guanosine nucleoside analog, is the most potent inhibitor of HBV replication on the market. Moreover, the naturally occurring carbocyclic nucleosides aristeromycin are known for their wide range of antiviral activities.
In this research, we have utilized BINAP directed rhodium catalyzed reductive carbocyclization of 1,6-enynes (8a–b) through asymmetric hydrogenation which is an approach, not yet explored in carbocyclic sugar synthesis. Interestingly, we obtained exclusive anti-(9a) and Z-anti (9b) carbocyclic sugars. The new aristeromycin analogs (10a–b) with scaffold combination of entecavir and aristeromycin were then synthesized using the Mitsunobu reaction followed by deprotection. 相似文献
12.
《Nucleosides, nucleotides & nucleic acids》2013,32(9):1747-1755
Abstract Vinylogously extended deoxyeritadenine derivatives were synthesized as acyclic/carbocyclic analogues of the 6′-halo(homovinyl)adenosines, which are known to be potent inhibitors of S-adenosyl-L-homocysteine hydrolase. Swern oxidation of 9-[3-(t-butyldimethylsilyloxy)-4-hydroxybutyl]adenine (4) followed by Wittig olefination and desilylation gave access to ethyl 6-(adenin-9-yl)-4-hydroxy-2(E)-hexenoate (7) and 5-(adenin-9-yl)-1,1-dibromo-1-penten-3-ol (9). No inhibition of AdoHcy Hydrolase was observed with 7 and 9. 相似文献
13.
《Nucleosides, nucleotides & nucleic acids》2013,32(4-7):1137-1139
New carbocyclic nucleosides with purine (compounds 3a and 3b), and 8-azapurine (compounds 3c and 3d) as base were prepared and assayed for in vitro activity. 相似文献
14.
M. I. Nieto J. M. Blanco O. CaamañTo F. Fernández X. García-Mera J. Balzarini 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1255-1266
Abstract Six new carbocyclic nucleosides were prepared by mounting a purine (compounds 5–7), 8-azapurine (compounds 9 and 10) or pyrimidine (compound 13) base on the amino group of (1R,cis)-3-(aminornethyl)-1,2,2-trimethylcyclopentylmethanol (2). The antiviral activity of compounds 5–7, 10 and 13, and their cytostatic activity, were evaluated. At subtoxic concentrations, the compounds showed no or marginal antiviral activity. Compound 5 showed moderate inhibition on tumor cell proliferation. 相似文献
15.
《Nucleosides, nucleotides & nucleic acids》2013,32(11):1995-2001
Abstract An efficient synthesis of 5′-nor carbocyclic ribavirin (4) is described in 13 steps from conveniently available (+)-(1R,4S)-4-hydroxy-2-cyclopenten-1-yl acetate (6). Compound 4 was evaluated against the following viruses: herpes simplex type 1 and 2, vaccinia, cowpox, smallpox, Ebola, hepatitis B, hepatitis C, adenovirus type 1, influenza A (H1N1 and H3N2), influenza B, parainfluenza type 3, Pichinde, Punta Toro A, respiratory syncytial, rhinovirus type 2, Venezuelan equine encephalitis, yellow fever, and West Nile. No activity was found nor was there any cytotoxicity to the viral host cells. 相似文献
16.
Yoshio Taniyama Tsunehiko Fukuda Ryuji Marumoto 《Nucleosides, nucleotides & nucleic acids》2013,32(2-4):529-549
Abstract Treating carbocyclic N1-methoxymethyl-inosine and -2′-deoxyinosine with 1N-NaOH/aq.EtOH gave carbocyclic 5-amino-4-imidazolecarboxamide riboside and 2′-deoxyriboside, respectively. Reactions of both the useful key intermediates with benzoylisothiocyanate afforded the corresponding 5-(N-benzoylisothiocarbamoyl) derivatives. Methylation of the sulfhydryl groups, followed by treatment with NaOH, led to the purine ring-closure (guanine, isoguanine, and 3-methylxanthine) reaction. The conformational difference between 2′-deoxyguanosine and carbocyclic 2′-deoxyguanosine is also discussed. 相似文献
17.
Isabel Nieto M. José Figueira J. Manuel Blanco Olga Caamaño Franco Fernández Erik De Clercq 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):641-642
Abstract New carbocyclic nucleosides with purine (compounds 2a-2c), 8-azapurine (compounds 2d and 2e) or pyrimidine (compound 3) as base were prepared and assayed for in vitro activity. 相似文献
18.
Anne Popescu Anna-Britta Hörnfeldt Salo Gronowitz Nils Gunnar Johansson 《Nucleosides, nucleotides & nucleic acids》2013,32(8):1639-1657
Abstract Some carbocyclic uridines and cytidines have been dihydroxylated in an osmium catalyzed reaction. Besides the nucleoside analogues, the anti forms, the diastereomeric syn forms were formed. These could be separated and tested with regard to antiviral activity. 相似文献
19.
Victor E. Marquez Abdallah Ezzitouni Maqbool A. Siddiqui Pamela Russ Hisafumi Ikeda Clifford George 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1431-1434
Abstract A conformational analysis of carbocyclic nucleosides built on a rigid bicyclo[3.1.0]hexane template (1–4, Northern and 5–8 Southern) showed that the Northern conformation prefers an anti glycosyl torsion angle whereas the Southern conformation favors the syn range. Antiviral activity was mostly associated with the Northern conformers. 相似文献
20.
《Nucleosides, nucleotides & nucleic acids》2013,32(4-7):1127-1128
Seven new carbocyclic nucleosides derived from indan (1a–g) were efficiently prepared from 1,2-indanedimethanol vía Mitsunobu reaction with 6-chloroadenine and subsequent introduction of the appropriate substituent. 相似文献