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

• Published in: Heteroatom chemistry Vol. 13; no. 1; pp. 77 - 83
• Main Authors: Wang, Lijuan J., Grapperhaus, Margaret L., Pitzele, Barnett S., Hagen, Timothy J., Fok, Kam F., Scholten, Jeffrey A., Spangler, Dale P., Toth, Mihaly V., Jerome, Gina M., Moore, William M., Manning, Pamela T., Sikorski, James A.
• Format: Journal Article
• Language: English
• Published: New York John Wiley & Sons, Inc 2002
• ISSN: 1042-7163; 1098-1071
• DOI: 10.1002/hc.1109

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