Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitors: 2-oxetanones with a side chain mimicking the folded structure of 1233A.

DOI: 10.1248/cpb.42.512

Source and publish data:

Chemical and pharmaceutical bulletin p. 512 - 520 (1994)

Update date:2022-08-04

Topics:

Authors:

Hashizume

Ito Ito

Yamada Yamada

Nagashima

Kanao Kanao

Tomoda Tomoda

Sunazuka

Kumagai Kumagai

Omura Omura

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Article abstract of DOI:10.1248/cpb.42.512

To mimic the folded side chain conformation of 1233A (1), which is a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitor, 1233A analogs with aromatic rings in the side chain were synthesized. The 2-oxetanone moiety was kept intact. Among 1233A and its synthetic analogs, trans-3-hydroxymethyl-4-[2-(7-methoxycarbonyl-1-naphthyl)ethyl]-2-oxe tanone (23) showed the highest HMG-CoA synthase inhibitory activity in vitro. The structure-activity relationship at the side chain is discussed.

Full text of DOI:10.1248/cpb.42.512

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