Synthesis and cytogenetic studies of structure--biological activity relationship of esters of Hecogenin and aza-homo-Hecogenin with N,N-bis(2-chloroethyl)aminocinnamic acid isomers

Steroids. 2005 Aug;70(9):586-93. doi: 10.1016/j.steroids.2005.02.018.

Abstract

The esters of Hecogenin and aza-homo-Hecogenin with N,N-bis(2-chloroethyl)aminocinnamic acid isomers have been prepared and their cytogenetic studies of structure-biological activity relationship were evaluated. The cytogenetic effects (sister chromatid exchanges (SCEs) induction and proliferation rate indices (PRIs) depression) by o-, m- and p-[N,N-bis(2-chloroethyl)amino] cinnamic acid were also investigated. Among the above compounds tested, those of the m-[N,N-bis(2-chloroethyl)amino] cinnamic acid and of the o-[N,N-bis(2-chloroethyl)amino] cinnamic acid ester of aza-homo-Hecogenin were more active in comparison to the others.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / pharmacology
  • Cell Proliferation / drug effects
  • Cinnamates / chemistry*
  • Esterification
  • Humans
  • Isomerism
  • Lymphocytes / drug effects
  • Molecular Structure
  • Mutagenicity Tests
  • Nitrogen Mustard Compounds / chemical synthesis*
  • Nitrogen Mustard Compounds / pharmacology
  • Sapogenins / chemistry*
  • Sapogenins / pharmacology
  • Sister Chromatid Exchange / drug effects
  • Sister Chromatid Exchange / genetics
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Aza Compounds
  • Cinnamates
  • Nitrogen Mustard Compounds
  • Sapogenins
  • cinnamic acid
  • hecogenin