4,1-Benzoxazepinone analogues of efavirenz (Sustiva (TM)) as HIV-1 reversetranscriptase inhibitors

Authors
Cocuzza, AJ Chidester, DR Cordova, BC Klabe, RM Jeffrey, S Diamond, S Weigelt, CA Ko, SS Bacheler, LT Erickson-Viitanen, SK Rodgers, JD
Citation
Aj. Cocuzza et al., 4,1-Benzoxazepinone analogues of efavirenz (Sustiva (TM)) as HIV-1 reversetranscriptase inhibitors, BIOORG MED, 11(11), 2001, pp. 1389-1392
Citations number
11
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
11
Issue
11
Year of publication
2001
Pages
1389 - 1392
Database
ISI
SICI code
0960-894X(20010604)11:11<1389:4AOE((>2.0.ZU;2-X
Abstract
A series of 4,1-benzoxazepinone analogues of efavirenz (Sustiva(TM)) as pot ent NNRTIs has been discovered. The cis-3-alkylbenzoxazepinones are more po tent then the trans isomers and can be synthesized preferentially by a nove l stereoselective cyclization. The best compounds are potent orally bioavai lable inhibitors of both wild-type HIV-1 and its clinically relevant K103N mutant virus, but are highly protein-bound in human plasma. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights res erved.