9-HYDROXYMETHYLCYCLOPROPYLIDENEMETHYLENYLADENINE - THE DESIGN, FACILESYNTHESIS, ISOMER SEPARATION AND ANTI-HIV-1 ACTIVITIES

Authors
CHENG CM SHIMO T SOMEKAWA K BABA M
Citation
Cm. Cheng et al., 9-HYDROXYMETHYLCYCLOPROPYLIDENEMETHYLENYLADENINE - THE DESIGN, FACILESYNTHESIS, ISOMER SEPARATION AND ANTI-HIV-1 ACTIVITIES, Tetrahedron, 54(10), 1998, pp. 2031-2040
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
10
Year of publication
1998
Pages
2031 - 2040
Database
ISI
SICI code
0040-4020(1998)54:10<2031:9-TDF>2.0.ZU;2-L
Abstract
9-Hydroxymethylcyclopropylidenemethylenyladenine was designed based on the analysis of the structure-activity relationship and synthesized b y coupling reaction of a vicinal dibromocyclopropane derivative with a denine. The cis/trans isomers and an enantiomer of the cis-isomer of t he cyclic alpha, beta-unsaturated nucleosides derived by reduction wer e separated by reverse phase HPLC and chiral HPLC, respectively. The c is-isomer was effective against HIV-1 and the (-)cis-isomer was highly effective with EC50 13 mu M. (C) 1998 Elsevier Science Ltd. All right s reserved.