Fluorinated sugar analogues of potential anti-HIV-1 nucleosides Journal Article
| Authors: | Huang, J. T.; Chen, L. C.; Wang, L.; Kim, M. H.; Warshaw, J. A.; Armstrong, D.; Zhu, Q. Y.; Chou, T. C.; Watanabe, K. A.; Matulic-Adamic, J.; Su, T. L.; Fox, J. J.; Polsky, B.; Baron, P. A.; Gold, J. W. M.; Hardy, W. D.; Zuckerman, E. |
| Article Title: | Fluorinated sugar analogues of potential anti-HIV-1 nucleosides |
| Abstract: | In order to obtain agents with therapeutic indices superior to those of AZT, FLT, or D4T, several analogues of anti-HIV-1 nucleosides were synthesized. These include 2′,3′-dideoxy-2′,3′-difluoro-5-methyluridine (13), its arabino analogue 19, arabino-5-methylcytosine analogue 21, 3′-deoxy-2′,3′-didehydro-2′-fluorothymidine (25), 3′-azido- 2′,3′-dideoxy-2′-fluoro-5-methyluridine (29), 2′-azido-3′-fluoro-2′,3′-dideoxy-5-methyluridine (31), and 2′,3′-dideoxy-2′-fluoro-5-methyluridine (37). These new nucleosides were screened for their activity against HIV and feline TLV in vitro. None of the compounds showed significant activity. It is interesting to note that such a small modification in the sugar moiety of active anti-HIV nucleosides (i.e., displacement of hydrogen by fluorine) almost completely inactivate the agents. © 1991, American Chemical Society. All rights reserved. |
| Keywords: | human cell; nonhuman; animal cell; animal; cells, cultured; cytotoxicity; drug synthesis; structure-activity relationship; chemistry; antivirus agent; antiviral activity; human immunodeficiency virus 1; nucleoside; hiv-1; zidovudine; antiviral agents; mink; dideoxynucleosides; murine leukemia virus; human; priority journal; article; support, u.s. gov't, p.h.s.; organofluorine derivative |
| Journal Title: | Journal of Medicinal Chemistry |
| Volume: | 34 |
| Issue: | 5 |
| ISSN: | 0022-2623 |
| Publisher: | American Chemical Society |
| Date Published: | 1991-05-01 |
| Start Page: | 1640 |
| End Page: | 1646 |
| Language: | English |
| DOI: | 10.1021/jm00109a017 |
| PUBMED: | 2033590 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 27 September 2019 -- Source: Scopus |
