Conformational properties and M1 antimuscarinic activity of 4-substituted pirenzepine/telenzepine analogues

Yuki Kanase, Kosho Makino, Takashi Yoshinaga, Hidetsugu Tabata, Tetsuta Oshitari, Hideaki Natsugari, Hideyo Takahashi

Research output: Contribution to journalArticle

Abstract

The atropisomeric and conformational properties of the 4-Cl/Me-substituted pirenzepine/telenzepine analogues were examined. Although the 4-substitution is not effective in reducing the rotational barrier of the N5-(C1'=O) bond, the butterfly motion of the tricyclic ring system was frozen. The atropisomers showed little racemization after heating at 80 °C for 5 days. While these analogues showed less affinity to the M1 receptor compared with pirenzepine, a ca. 4.4-fold difference in potency between the atropisomers was observed for 1b.

Original languageEnglish
Pages (from-to)273-283
Number of pages11
JournalHeterocycles
Volume101
Issue number1
DOIs
Publication statusPublished - 1 Jan 2020

    Fingerprint

Cite this