ISSN:
0170-2041
Keywords:
Thymidine derivatives
;
Azides
;
HIV
;
Carbohydrates
;
Nucleosides
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Compound 15 - the 2′-azido analog of the anti-HIV compound 2′,3′-didehydro-2′,3′-dideoxythymidine - was synthesized. Treatment of 5′-O-trityl-β-D-ribofuranosylthymine (1) with DAST or MSTF gave the 2,2′-anhydro derivative 2. The latter and its 3′-O-benzoate 3 were used for the synthesis of the 2′-azido-2′-deoxy derivatives 4 and 5. Two routes to the synthesis of 15 from 5 were investigated. (i) Treatment of 5 with DAST gave a mixture of the 5′-O-trityl derivatives 12 and 13 as well as 1-(2-azido-2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)thymine (16) along with 2,3′-anhydro derivative 14 (2%). Detritylation of the mixture yielded 15 (39%) and 16 (12%). (ii) Mesylation of 5 gave 17 which yielded 15 upon saponification and detritylation. Compound 15 showed moderate inhibitory activity against HIV-1 and HIV-2 in MT-4 cells.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930185
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