Chemical modification and structure-activity relationships of pyripyropenes. 2. 1,11-cyclic analogs

Rika Obata, Toshiaki Sunazuka, Yumiko Kato, Hiroshi Tomoda, Yoshihiro Harigaya, Satoshi Omura

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A series of 1,11-cyclic analogs of pyripyropene A were prepared. Replacement of the 1,11-acyl groups of pyripyropenes with 1,11-cyclic acetals effectively improved in vitro acyl CoA:cholesterol acyltransferase (ACAT) inhibitory activity. Especially noteworthy is benzylidene acetal analog 35, the most potent inhibitor (IC50 = 5.6 nM) among the derivatives prepared so far, which showed 16 times more potent inhibitory activity than pyripyropene A.

Original languageEnglish
Pages (from-to)1149-1156
Number of pages8
JournalJournal of Antibiotics
Volume49
Issue number11
Publication statusPublished - 1996
Externally publishedYes

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Acetals
Structure-Activity Relationship
Sterol O-Acyltransferase
Inhibitory Concentration 50
pyripyropene A
In Vitro Techniques

ASJC Scopus subject areas

  • Pharmacology
  • Molecular Medicine

Cite this

Obata, R., Sunazuka, T., Kato, Y., Tomoda, H., Harigaya, Y., & Omura, S. (1996). Chemical modification and structure-activity relationships of pyripyropenes. 2. 1,11-cyclic analogs. Journal of Antibiotics, 49(11), 1149-1156.

Chemical modification and structure-activity relationships of pyripyropenes. 2. 1,11-cyclic analogs. / Obata, Rika; Sunazuka, Toshiaki; Kato, Yumiko; Tomoda, Hiroshi; Harigaya, Yoshihiro; Omura, Satoshi.

In: Journal of Antibiotics, Vol. 49, No. 11, 1996, p. 1149-1156.

Research output: Contribution to journalArticle

Obata, R, Sunazuka, T, Kato, Y, Tomoda, H, Harigaya, Y & Omura, S 1996, 'Chemical modification and structure-activity relationships of pyripyropenes. 2. 1,11-cyclic analogs', Journal of Antibiotics, vol. 49, no. 11, pp. 1149-1156.
Obata R, Sunazuka T, Kato Y, Tomoda H, Harigaya Y, Omura S. Chemical modification and structure-activity relationships of pyripyropenes. 2. 1,11-cyclic analogs. Journal of Antibiotics. 1996;49(11):1149-1156.
Obata, Rika ; Sunazuka, Toshiaki ; Kato, Yumiko ; Tomoda, Hiroshi ; Harigaya, Yoshihiro ; Omura, Satoshi. / Chemical modification and structure-activity relationships of pyripyropenes. 2. 1,11-cyclic analogs. In: Journal of Antibiotics. 1996 ; Vol. 49, No. 11. pp. 1149-1156.
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