Design, Synthesis, and Antifungal Activity of 16,17-Dihydroheronamide C and ent-Heronamide C

  • J Org Chem. 2021 Dec 3;86(23):16249-16258. doi: 10.1021/acs.joc.1c01761.
Naoki Kanoh  1  2 ,  Ryusei Terashima  3 ,  Hiromichi Nishiyama  3 ,  Yuta Terajima  3 ,  Shota Nagasawa  3 ,  Yusuke Sasano  3 ,  Yoshiharu Iwabuchi  3 ,  Hiroaki Saito  4 ,  Syusuke Egoshi  5 ,  Kosuke Dodo  5 ,  Mikiko Sodeoka  5 ,  Chengqian Pan  6 ,  Yoshinobu Ikeuchi  6 ,  Shinichi Nishimura  7 ,  Hideaki Kakeya  6
Affiliations
  • 1. School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan.
  • 2. Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan.
  • 3. Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
  • 4. Faculty of Pharmaceutical Sciences, Hokuriku University, 3 Kanagawamachi, Kanazawa, Ishikawa 920-1181, Japan.
  • 5. Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
  • 6. Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Shimo-Adachi-cho, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
  • 7. Department of Biotechnology, Collaborative Research Institute for Innovative Microbiology, The University of Tokyo, Tokyo 113-8657, Japan.
PMID: 34784214 DOI: 10.1021/acs.joc.1c01761
Abstract

16,17-Dihydroheronamide C (8) and ent-heronamide C (ent-1) were designed as probes for the mode-of-action analysis of heronamide C (1). These molecules were synthesized by utilizing a highly modular strategy developed in the preceding paper. The evaluation of the Antifungal activity of these compounds revealed the exceptional importance of the C16-C17 double bond for the Antifungal activity of heronamide C and the existence of chiral recognition between heronamide C (1) and cell membrane components.

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