(E)-2-Benzylidenebenzocyclanones: Part XIII - (E)/(Z)-Isomerization of some cyclic chalcone analogues. Effect of ring size on lipophilicity of geometric isomers

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Optimized isocratic reverse phase high-performance liquid chromatography (RP-HPLC) method was developed for separation of the respective (E) and (Z) isomers of the cyclic chalcone analogues (E)-2-(4′-X-benzylidene)-1-indanones, -tetralones, and -benzosuberones. The method has been applied to monitor progress of the light-induced (E)/(Z) isomerization process in the three series. Data indicate formation of equilibrium mixtures of the respective geometric isomers. Comparison of the HPLC retention factors of the respective geometric isomers showed the (Z) isomers less lipophilic in the benzosuberone and the tetralone but more lipophilic in the indanone series. Data provide experimental evidence of opposite effect of ring size and geometric isomerism on lipophilicity of conformationally restricted (cyclic) analogues of chalcone, an open chain pharmacophore. Graphical abstract: [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)1275-1281
Number of pages7
JournalMonatshefte fur Chemie
Volume146
Issue number8
DOIs
Publication statusPublished - Aug 29 2015

Keywords

  • (E)/(Z) Isomerization
  • Cyclic chalcone analogues
  • Equilibrium isomeric mixtures
  • Lipophilicity
  • Photochemistry

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of '(E)-2-Benzylidenebenzocyclanones: Part XIII - (E)/(Z)-Isomerization of some cyclic chalcone analogues. Effect of ring size on lipophilicity of geometric isomers'. Together they form a unique fingerprint.

  • Cite this