Synthesis and anticancer activity of a novel class of flavonoids: 2,4-diarylchromane[4,3-d]-delta(1,9b)-1,2,3-thiadiazolines

Huazhou Ying; Yongzhou Hu; Qiaojun He; Runping Li; Bo Yang

doi:10.1016/j.ejmech.2006.10.004

Synthesis and anticancer activity of a novel class of flavonoids: 2,4-diarylchromane[4,3-d]-delta(1,9b)-1,2,3-thiadiazolines

Eur J Med Chem. 2007 Feb;42(2):226-34. doi: 10.1016/j.ejmech.2006.10.004. Epub 2006 Nov 28.

Authors

Huazhou Ying¹, Yongzhou Hu, Qiaojun He, Runping Li, Bo Yang

Affiliation

¹ ZJU-ENS Joint Laboratory of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang 310058, China.

PMID: 17137679
DOI: 10.1016/j.ejmech.2006.10.004

Abstract

A series of 2,4-diarylchromane[4,3-d]-Delta(1,9b)-1,2,3-thiadiazolines have been synthesized by cyclization of corresponding 2-arylchroman-4-one-arylhydrazones with SOCl(2) then treated with alcohol. All the compounds have been tested for their antiproliferative activity in vitro against six human tumor cell lines, and the highly potent derivative 11a exhibited in vivo inhibitory effect on tumor growth. Mechanism research indicated that it is due to 11a that induces DNA fragmentation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology
Cell Line, Tumor
Chromans / chemical synthesis*
Chromans / chemistry
Chromans / pharmacology
Crystallography, X-Ray
DNA Fragmentation
Drug Screening Assays, Antitumor
Flavonoids / chemical synthesis*
Flavonoids / chemistry
Flavonoids / pharmacology
Humans
Magnetic Resonance Spectroscopy
Molecular Structure
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared
Stereoisomerism
Structure-Activity Relationship
Thiadiazoles / chemical synthesis*
Thiadiazoles / chemistry
Thiadiazoles / pharmacology

Substances

Antineoplastic Agents
Chromans
Flavonoids
Thiadiazoles