Synthesis and structure-activity relationship of pyripyropene A derivatives as potent and selective acyl-CoA:cholesterol acyltransferase 2 (ACAT2) inhibitors: part 2

Masaki Ohtawa; Hiroyuki Yamazaki; Daisuke Matsuda; Taichi Ohshiro; Lawrence L Rudel; Satoshi Ōmura; Hiroshi Tomoda; Tohru Nagamitsu

doi:10.1016/j.bmcl.2013.02.088

Synthesis and structure-activity relationship of pyripyropene A derivatives as potent and selective acyl-CoA:cholesterol acyltransferase 2 (ACAT2) inhibitors: part 2

Bioorg Med Chem Lett. 2013 May 1;23(9):2659-62. doi: 10.1016/j.bmcl.2013.02.088. Epub 2013 Mar 6.

Authors

Masaki Ohtawa¹, Hiroyuki Yamazaki, Daisuke Matsuda, Taichi Ohshiro, Lawrence L Rudel, Satoshi Ōmura, Hiroshi Tomoda, Tohru Nagamitsu

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Tokyo 108 8641, Japan.

PMID: 23535327
DOI: 10.1016/j.bmcl.2013.02.088

Abstract

Synthesis and structure-activity relationships of 7-O-p-cyanobenzoyl pyripyropene A derivatives with modification at C1 and 11 are described. Regioselective mono-deprotection of di-tert-butylsilylene acetal was critical in their synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Butanes / chemistry
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / metabolism
Protein Binding
Pyridines / chemical synthesis
Pyridines / chemistry*
Pyridines / metabolism
Sesquiterpenes / chemical synthesis
Sesquiterpenes / chemistry*
Sesquiterpenes / metabolism
Silanes / chemistry
Stereoisomerism
Sterol O-Acyltransferase / antagonists & inhibitors*
Sterol O-Acyltransferase / metabolism
Sterol O-Acyltransferase 2
Structure-Activity Relationship

Substances

Butanes
Enzyme Inhibitors
Pyridines
Sesquiterpenes
Silanes
di-tert-butylsilylene
pyripyropene A
Sterol O-Acyltransferase
sterol O-acyltransferase 1