Total synthesis of schizocommunin and revision of its structure

J Nat Prod. 2013 Nov 22;76(11):2034-9. doi: 10.1021/np400263f. Epub 2013 Oct 30.

Abstract

A proposed structure for schizocommunin (Z)-1(hydroxy) and its geometric isomer (E)-1(hydroxy), which exist in a keto form, has been synthesized. However, the spectroscopic data of (Z)-1(keto) and (E)-1(keto) were not consistent with those reported for natural schizocommunin. After reinvestigating the spectral data for natural schizocommunin, we synthesized the quinazolinone derivative (Z)-2 as a revised structure for schizocommunin. All of the spectral data of (Z)-2 were completely identical to those reported for natural schizocommunin. (Z)-2 showed moderate antiproliferative activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Indoles / pharmacology
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Indoles
  • schizocommunin