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

doi:10.7164/antibiotics.49.1149

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 journal › Article › peer-review

30 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 language	English
Pages (from-to)	1149-1156
Number of pages	8
Journal	Journal of Antibiotics
Volume	49
Issue number	11
DOIs	https://doi.org/10.7164/antibiotics.49.1149
Publication status	Published - 1996
Externally published	Yes

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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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.",

author = "Rika Obata and Toshiaki Sunazuka and Yumiko Kato and Hiroshi Tomoda and Yoshihiro Harigaya and Satoshi Omura",

year = "1996",

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language = "English",

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journal = "Journal of Antibiotics",

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T1 - Chemical modification and structure-activity relationships of pyripyropenes. 2. 1,11-cyclic analogs

AU - Obata, Rika

AU - Sunazuka, Toshiaki

AU - Kato, Yumiko

AU - Tomoda, Hiroshi

AU - Harigaya, Yoshihiro

AU - Omura, Satoshi

PY - 1996

Y1 - 1996

N2 - 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.

AB - 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.

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UR - https://www.scopus.com/pages/publications/0029857704#tab=citedBy

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M3 - Article

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SN - 0021-8820

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JO - Journal of Antibiotics

JF - Journal of Antibiotics

IS - 11

ER -

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

Abstract

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