Dibasic benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors: 4. SAR studies on the conformationally restrictedC3-side chain of hydroxybenzo[b]thiophenes

Authors
Takeuchi, K Kohn, TJ Sall, DJ Denney, ML McCowan, JR Smith, GF Gifford-Moore, DS
Citation
K. Takeuchi et al., Dibasic benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors: 4. SAR studies on the conformationally restrictedC3-side chain of hydroxybenzo[b]thiophenes, BIOORG MED, 9(5), 1999, pp. 759-764
Citations number
11
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
9
Issue
5
Year of publication
1999
Pages
759 - 764
Database
ISI
SICI code
0960-894X(19990308)9:5<759:DBDAAN>2.0.ZU;2-0
Abstract
A novel series of benzo[b]thiophene diamine thrombin inhibitors with a conf ormationally restricted C3-side chain 3 was investigated. The constrained C 3-side chain by a cyclohexyl ring contributed to not only an additive but a lso a synergistic effect on the thrombin inhibitory activity. The SAR studi es resulted in the discovery of a potent thrombin inhibitor 27 that was ove r 750-fold more potent than the initial lead compound 1. (C) 1999 Elsevier Science Ltd. All rights reserved.