Synthesis and characterization of two homologous series of diastereomeric 2-alkoxyphenylcarbamates

Chem Pharm Bull (Tokyo). 2011;59(8):978-83. doi: 10.1248/cpb.59.978.

Abstract

Two homologous series of racemic diastereomeric cis- and trans-(2-dimethylaminomethylcycloheptyl)-2-alkoxyphenylcarbamates with alkyl chain lengths ranging from C₁ to C₈ were synthesized by stereoselective reactions. The chemical structures of these compounds were confirmed by ¹H-NMR, ¹³C-NMR and IR spectroscopy and their physico-chemical properties were characterized. The two new series of diastereomeric compounds were tested for their local anesthetic activity and parabolic relationship between the local anesthetic activity and lipophilicity was found for both cis- and trans-series. Interestingly, cis-stereoisomers exhibited higher local anesthetic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anesthetics, Local / chemical synthesis
  • Anesthetics, Local / chemistry*
  • Anesthetics, Local / pharmacology*
  • Animals
  • Cornea / drug effects
  • Magnetic Resonance Spectroscopy
  • Phenylcarbamates / chemical synthesis
  • Phenylcarbamates / chemistry*
  • Phenylcarbamates / pharmacology*
  • Rabbits
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Anesthetics, Local
  • Phenylcarbamates