Synthesis 2015; 47(19): 2976-2984
DOI: 10.1055/s-0034-1380437
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Cytotoxic Activity of N,N′-(Arylmethylene)bisamides

Junichi Uenishi*
a   Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan   Email: juenishi@mb.kyoto-phu.ac.jp
,
Hirokazu Hirano
a   Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan   Email: juenishi@mb.kyoto-phu.ac.jp
,
Tsuyoshi Ueda
a   Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan   Email: juenishi@mb.kyoto-phu.ac.jp
,
Naoyuki Hoshiya
a   Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan   Email: juenishi@mb.kyoto-phu.ac.jp
,
Hiromi Ii
b   Department of Clinical Oncology, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan   Email: yoshiki@mb.kyoto-phu.ac.jp
,
Tatsuhiro Yoshiki*
b   Department of Clinical Oncology, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan   Email: yoshiki@mb.kyoto-phu.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 23 April 2015

Accepted after revision: 11 May 2015

Publication Date:
09 July 2015 (online)


Abstract

N,N′-(Arylmethylene)bisamides were prepared by an acid-catalyzed reaction of arylaldehydes with cinnamamide or acrylamides. The reaction was carried out in refluxing toluene for a few hours, and simple collection of the precipitate gave the desired products. The bisamides were designed as cytotoxic molecules based on the structure of the potently cytotoxic marine natural product (–)-zampanolide. The activities of the bisamides against two cancer cell lines were evaluated, and several compounds were found to show medium potency with IC50 values in the lower micromolar level.

Supporting Information

 
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