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

Naoki Kanoh, Ryusei Terashima, Hiromichi Nishiyama, Yuta Terajima, Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi, Hiroaki Saito, Syusuke Egoshi, Kosuke Dodo, Mikiko Sodeoka, Chengqian Pan, Yoshinobu Ikeuchi, Shinichi Nishimura, Hideaki Kakeya

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)16249-16258
Number of pages10
JournalJournal of Organic Chemistry
Volume86
Issue number23
DOIs
Publication statusPublished - 2021 Dec 3
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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