Syntheses of new conformationally constrained S-[2-[(1-iminoethyl)amino] ethyl]homocysteine derivatives as potential nitric oxide synthase inhibitors

✍ Scribed by Lijuan J. Wang; Margaret L. Grapperhaus; Barnett S. Pitzele; Timothy J. Hagen; Kam F. Fok; Jeffrey A. Scholten; Dale P. Spangler; Mihaly V. Toth; Gina M. Jerome; William M. Moore; Pamela T. Manning; James A. Sikorski

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 158 KB
• Volume: 13
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.1109

✦ Synopsis

Abstract

The efficient syntheses of two new types of conformationally constrained S‐[2‐[(1‐iminoethyl)amino]ethyl]homocysteine derivatives, 1‐amino‐3‐[2[(1‐iminoethyl)amino]ethylthio]cyclobutane carboxylic Acid (5) and (4S)‐4‐[[2‐[(1‐Iminoethyl)amino]ethyl]thio]‐L‐proline (6), are reported. These molecules represent the first attempts to probe conformational constraint near the α‐amino acid moiety of known homocysteine‐based inhibitors of nitric oxide synthase. Targets 5 and 6 were evaluated as potential inhibitors of the three human isoforms of nitric oxide synthase. © 2002 John Wiley & Sons, Inc. Heteroatom Chem 13:77–83, 2002; DOI 10.1002/hc.1109