Synthesis and MMP-Inhibitory Activity of Gelastatin Analogues

✍ Scribed by Ju-Hee Cho; Soo Y. Ko; Eugene Oh; Jae C. Park; Ji U. Yoo

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: German
• Weight: 113 KB
• Volume: 85
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/1522-2675(200211)85:11<3994::aid-hlca3994>3.0.co;2-2

✦ Synopsis

Dedicated to Professor Dieter Seebach on the occasion of his 65th birthday

Gelastatin A and B, isolated from culture broth of Westerdykella multispora F 50733, have been reported to exhibit MMP-inhibitory activities at a sub-micromolar level. In an effort to exploit this lead, we synthesized gelastatin analogues in which the conjugated triene unit of natural gelastatins was replaced by the benzylidene group. The (Z)-isomeric synthetic benzylidene-gelastatin exhibited MMP-inhibitory activities comparable to those reported for the natural products. Therefore, this compound appears to be a viable lead in searching for therapeutically useful MMP inhibitors.