Structure–Activity Relationships of Thiophene Carboxamide Annonaceous Acetogenin Analogs: Shortening the Alkyl Chain in the Tail Part Significantly Affects Their Growth Inhibitory Activity against Human Cancer Cell Lines

• Ohta Kaito

  Kyoto Pharmaceutical University

• Akatsuka Akinobu

  Cancer Chemotherapy Center, Japanese Foundation for Cancer Research

• Dan Shingo

  Cancer Chemotherapy Center, Japanese Foundation for Cancer Research

• Iwasaki Hiroki

  Kyoto Pharmaceutical University

• Yamashita Masayuki

  Kyoto Pharmaceutical University

• Kojima Naoto

  Kyoto Pharmaceutical University

Abstract

In a previous study, we found that the thiophene carboxamide solamin analog, which is a mono-tetrahydrofuran annonaceous acetogenin, showed potent antitumor activity through the inhibition of mitochondrial complex I. In this study, we synthesized analogs with short alkyl chains instead of the n-dodecyl group in the tail part. We evaluated their growth inhibitory activities against human cancer cell lines. We found that the alkyl chain in the tail part plays an essential role in their activity.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 69 (10), 1029-1033, 2021-10-01

  The Pharmaceutical Society of Japan

Keywords

• annonaceous acetogenin
• antitumor agent
• structure–activity relationship
• organic synthesis

Details

• CRID: 1390289564742471552
• NII Article ID: 130008095541
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c21-00450
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 031714216
• PubMed: 34602571
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I031714216
• Web Site: https://www.jstage.jst.go.jp/article/cpb/69/10/69_c21-00450/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2022251285
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed