Optically active iodohelicene derivatives exhibit histamine N-methyl transferase inhibitory activity

Wataru Ichinose, Tsukasa Sawato, Haruna Kitano, Yasuhiro Shinozaki, Mieko Arisawa, Nozomi Saito, Takeo Yoshikawa, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

Abstract

Optically active helicene derivatives inhibit the activity on histamine N-methyl transferase (HNMT). Specifically, methyl (P)-1,12-dimethylbenzo[c]phenanthrene-8-carboxylate with 6-iodo and 5-trifluoromethanesulfonyloxy groups inhibits HNMT activity on the μM order of IC 50 . Chirality is important, and (M)-isomers exhibits substantially reduced activity. The 6-iodo group is also essential, which suggests the involvement of halogen bonds in protein binding. Substituents on the sulfonate moiety also affect the inhibitory activity.

Original languageEnglish
Pages (from-to)476-481
Number of pages6
JournalJournal of Antibiotics
Volume72
Issue number6
DOIs
Publication statusPublished - Jun 1 2019
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery

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