Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues

Authors
Singh, SB Graham, PL Reamer, RA Cordingley, MG
Citation
Sb. Singh et al., Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues, BIOORG MED, 11(24), 2001, pp. 3143-3146
Citations number
14
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
11
Issue
24
Year of publication
2001
Pages
3143 - 3146
Database
ISI
SICI code
0960-894X(200112)11:24<3143:DTSH3I>2.0.ZU;2-V
Abstract
2-Methoxystypandrone, a naphthoquinone. was isolated from a Chinese herb Po lygonum cuspidatum by bioassay guided fractionation using HRV 3C-protease a ssay. It showed an IC50 value of 4.6 muM and is moderately selective. A new 10-step, total synthesis of 2-methoxystypandrone was accomplished in 45% o verall yield using a Diels-Alder approach. Several analogues of this compou nd were prepared. Isolation, synthesis and HRV 3C-protease structure activi ty relationships of these compounds have been described. (C) 2001 Elsevier Science Ltd. All rights reserved.