Synthesis and anti-HIV activity of 2'-deoxy-2'-fluoro-4'-C-ethynyl nucleoside analogs.
Publication
, Journal Article
Wang, Q; Li, Y; Song, C; Qian, K; Chen, C-H; Lee, K-H; Chang, J
Published in: Bioorg Med Chem Lett
July 15, 2010
Based on the favorable antiviral profiles of 4'-substituted nucleosides, novel 1-(2'-deoxy-2'-fluoro-4'-C-ethynyl-beta-D-arabinofuranosyl)-uracil (1a), -thymine (1b), and -cytosine (2) analogs were synthesized. Compounds 1b and 2 exhibited potent anti-HIV-1 activity with IC(50) values of 86 and 1.34 nM, respectively, without significant cytotoxicity. Compound 2 was 35-fold more potent than AZT against wild-type virus, and also retained nanomolar antiviral activity against resistant strains, NL4-3 (K101E) and RTMDR. Thus, 2 merits further development as a novel NRTI drug.
Duke Scholars
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Published In
Bioorg Med Chem Lett
DOI
EISSN
1464-3405
Publication Date
July 15, 2010
Volume
20
Issue
14
Start / End Page
4053 / 4056
Location
England
Related Subject Headings
- Virus Replication
- Medicinal & Biomolecular Chemistry
- Humans
- HIV-1
- Deoxyribonucleosides
- Cell Line
- Anti-HIV Agents
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 1115 Pharmacology and Pharmaceutical Sciences
Citation
APA
Chicago
ICMJE
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Wang, Q., Li, Y., Song, C., Qian, K., Chen, C.-H., Lee, K.-H., & Chang, J. (2010). Synthesis and anti-HIV activity of 2'-deoxy-2'-fluoro-4'-C-ethynyl nucleoside analogs. Bioorg Med Chem Lett, 20(14), 4053–4056. https://doi.org/10.1016/j.bmcl.2010.05.090
Wang, Qiang, Yanfeng Li, Chuanjun Song, Keduo Qian, Chin-Ho Chen, Kuo-Hsiung Lee, and Junbiao Chang. “Synthesis and anti-HIV activity of 2'-deoxy-2'-fluoro-4'-C-ethynyl nucleoside analogs.” Bioorg Med Chem Lett 20, no. 14 (July 15, 2010): 4053–56. https://doi.org/10.1016/j.bmcl.2010.05.090.
Wang Q, Li Y, Song C, Qian K, Chen C-H, Lee K-H, et al. Synthesis and anti-HIV activity of 2'-deoxy-2'-fluoro-4'-C-ethynyl nucleoside analogs. Bioorg Med Chem Lett. 2010 Jul 15;20(14):4053–6.
Wang, Qiang, et al. “Synthesis and anti-HIV activity of 2'-deoxy-2'-fluoro-4'-C-ethynyl nucleoside analogs.” Bioorg Med Chem Lett, vol. 20, no. 14, July 2010, pp. 4053–56. Pubmed, doi:10.1016/j.bmcl.2010.05.090.
Wang Q, Li Y, Song C, Qian K, Chen C-H, Lee K-H, Chang J. Synthesis and anti-HIV activity of 2'-deoxy-2'-fluoro-4'-C-ethynyl nucleoside analogs. Bioorg Med Chem Lett. 2010 Jul 15;20(14):4053–4056.
Published In
Bioorg Med Chem Lett
DOI
EISSN
1464-3405
Publication Date
July 15, 2010
Volume
20
Issue
14
Start / End Page
4053 / 4056
Location
England
Related Subject Headings
- Virus Replication
- Medicinal & Biomolecular Chemistry
- Humans
- HIV-1
- Deoxyribonucleosides
- Cell Line
- Anti-HIV Agents
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 1115 Pharmacology and Pharmaceutical Sciences