Synthesis of quaternary ammonium salts of 16E-[4-(2-alkylaminoethoxy)-3-methoxybenzylidene]androstene derivatives as skeletal muscle relaxants

Ranju Bansal, Sheetal Guleria, Louise C Young, Alan L Harvey

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Synthesis of eighteen new quaternary ammonium salts of 16E-arylidene androstene derivatives as skeletal muscle relaxants is reported in the present study. The effects of possibly extended interonium distances on muscle relaxant activity are discussed. All the quaternary ammonium steroids produced reduction in the twitch responses, when screened for in vitro neuromuscular blocking activity using isolated chick biventer cervicis muscle preparation. However, the variable interonium distance, which is believed to range from 11 to 17 Å in these quaternary compounds and is associated with the built in flexibility of these structures about the single bonds on the moieties linked to ring D of the steroid skeleton, resulted in varied degrees of muscle relaxant activity. Some of the compounds also inhibited acetylcholinesterase activity in low concentrations so that they would not be directly suitable for use as muscle relaxants.
Original languageEnglish
Pages (from-to)254-260
Number of pages7
JournalSteroids
Volume76
Issue number3
DOIs
Publication statusPublished - Feb 2011

Keywords

  • anticholinesterase activity
  • Quaternary ammonium salts
  • 16E-Arylidene steroids
  • skeletal muscle relaxants

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