Total Synthesis of Schizocommunin and Revision of Its Structure

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...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2013-11, Vol.76 (11), p.2034-2039
Main Authors: Uehata, Koji, Kimura, Naoki, Hasegawa, Kazuya, Arai, Shigeru, Nishida, Mayumi, Hosoe, Tomoo, Kawai, Ken-ichi, Nishida, Atsushi
Format: Article
Language:English
Subjects:
Drug Screening Assays, Antitumor
HeLa Cells
Humans
Indoles - chemical synthesis
Indoles - chemistry
Indoles - pharmacology
Molecular Structure
Stereoisomerism
Structure-Activity Relationship
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Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np400263f