Factors influencing the interconversion of a new class of dibenzodiazepine sulfonamide atropisomers

Chirality. 2009:21 Suppl 1:E105-9. doi: 10.1002/chir.20785.

Abstract

A novel family of atropisomers based on a conformationally constrained seven membered ring system is investigated using a combination of preparative chiral chromatography, circular dichroism, and other analytical techniques. The influence of structure on the rate of atropisomer interconversion was explored with a series of analogs showing a range of interconversion rates ranging from very fast (undetectable on the HPLC timescale) to very slow (half life of many days).

MeSH terms

  • Antipsychotic Agents / chemistry*
  • Antipsychotic Agents / classification*
  • Chromatography, High Pressure Liquid / methods
  • Circular Dichroism / methods
  • Half-Life
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfonamides / chemistry*
  • Sulfonamides / classification*

Substances

  • Antipsychotic Agents
  • Sulfonamides