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. 2025 Jul 18.
doi: 10.2183/pjab.101.029. Online ahead of print.

Syntheses and biological evaluation of M-COPA analogs derived from pentadienoic Weinreb amide

Hisazumi Tsutsui  1 , Daiki Usukura  1 , Fumiya Watabe  1 , Hiroki Okano  1 , Ryo Hirata  1 , Ryunosuke Shiogama  1 , Yamato Kanai  1 , Saki Kato  1 , Yuki Asahara  1 , Sayaka Chogi  1 , Yingjia Lu  1 , Haruka Hirai  1 , Mai Kitamoto  1 , Miho Kojima  1 , Yuuki Obata  2 , Motoyuki Shimonaka  1 , Takatsugu Murata  1 , Isamu Shiina  1
Affiliations
Free article

Syntheses and biological evaluation of M-COPA analogs derived from pentadienoic Weinreb amide

Hisazumi Tsutsui et al. Proc Jpn Acad Ser B Phys Biol Sci. .
Free article

Abstract

M-COPA (1), which contains diene and 3-picolylamine moieties in its side chain and seven stereogenic centers in a multisubstituted octalin skeleton, strongly inhibits the growth of several cancer cell lines. Expecting the improvement of conformational flexibility of basic and coordinating 3-pyridylmethylamino group on M-COPA and its physical properties, we efficiently synthesized its amine analogs by replacing its amide group with an amino group through the Weinreb amide-type Horner-Wadsworth-Emmons reaction. The cytotoxic properties of 1 and its analogs were evaluated against NCI-H226, a lung cancer cell line, HeLa, a cervical cancer cell line, and GIST-T1, a gastrointestinal stromal tumor cell line. The evaluation results indicated that the structural alteration from amide moiety to amine moiety lowered the pharmacological activity but remained strong cytotoxicity.

Keywords: Horner–Wadsworth–Emmons reaction; M-COPA; cytotoxicity.

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