2. Academic Validation
  3. Design, Synthesis, and Antifungal Activity of 16,17-Dihydroheronamide C and ent-Heronamide C

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

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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