Enantio- and diastereoselective total synthesis of EI-1941-1, -2, and -3, inhibitors of interleukin-1β converting enzyme, and biological properties of their derivatives

Mitsuru Shoji, Takao Uno, Hideaki Kakeya, Rie Onose, Isamu Shiina, Hiroyuki Osada, Yujiro Hayashi

研究成果: Article査読

27 被引用数 (Scopus)

抄録

The first asymmetric total synthesis of EI-1941-1, -2, and -3, inhibitors of the interleukin-1β converting enzyme (ICE), has been accomplished, starting from a chiral epoxy iodoquinone 11, a key intermediate in our total synthesis of epoxyquinols A and B. Despite a failure to synthesize the inhibitors by our postulated biosynthetic route, we were able to diastereoselectively synthesize them via an intramolecular carboxypalladation with the key steps being a 6-endo cyclization mode followed by β-hydride elimination. The investigation of the biological properties of EI-1941-1, -2, and -3 and their derivatives disclosed them to be potent and effective ICE inhibitors with less cytotoxicity than EI-1941-1 and -2 in a cultured cell system.

本文言語English
ページ(範囲)9905-9915
ページ数11
ジャーナルJournal of Organic Chemistry
70
24
DOI
出版ステータスPublished - 2005 11月 25

ASJC Scopus subject areas

  • 有機化学

フィンガープリント

「Enantio- and diastereoselective total synthesis of EI-1941-1, -2, and -3, inhibitors of interleukin-1β converting enzyme, and biological properties of their derivatives」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル