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

by Fumiya WATABE , Mai KITAMOTO , Yingjia LU , Daiki USUKURA , Yamato KANAI , Miho KOJIMA , Ryunosuke SHIOGAMA , Hiroki OKANO , Ryo HIRATA , Saki KATO , Yuuki OBATA , Haruka HIRAI , Isamu SHIINA , Yuki ASAHARA , Motoyuki SHIMONAKA , Sayaka CHOGI , Takatsugu MURATA , Hisazumi TSUTSUI

in Aldehydes / Amides - chemistry / Analogs / Angiogenesis / Antineoplastic Agents - chemical synthesis / Antineoplastic Agents - chemistry / Antineoplastic Agents - pharmacology / Arthritis / Cancer / Cell growth / Cell Line, Tumor / Cell Proliferation - drug effects / Cervical cancer / Chemistry Techniques, Synthetic / Cytotoxicity / HeLa Cells / Horner–Wadsworth–Emmons reaction / Humans / Lung cancer / M-COPA / Physical properties / Reagents / Structure-Activity Relationship / Tumor cell lines

2025

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

2025

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

2025

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Journal Article

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

Fumiya WATABE,

Mai KITAMOTO,

Yingjia LU,

Daiki USUKURA,

Yamato KANAI,

Miho KOJIMA,

Ryunosuke SHIOGAMA,

Hiroki OKANO,

Ryo HIRATA,

Saki KATO,

Yuuki OBATA,

Haruka HIRAI,

Isamu SHIINA,

Yuki ASAHARA,

Motoyuki SHIMONAKA,

Sayaka CHOGI,

Takatsugu MURATA,

Hisazumi TSUTSUI

2025

Overview

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.

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Publisher

The Japan Academy

Subject

Aldehydes

/ Amides - chemistry

/ Analogs

/ Angiogenesis

/ Antineoplastic Agents - chemical synthesis

/ Antineoplastic Agents - chemistry

/ Antineoplastic Agents - pharmacology