Synthesis and cytotoxic evaluation of quinazolin-4(3H)-one derivatives bearing thiocarbamate, thiourea or N-methyldithiocarbamate side chains

We have previously found that the dithiocarbamate derivatives of quinazolin-4(3H)-one could act as cytotoxic agents against a panel of human tumor cell lines. To investigate the contribution of dithiocarbamate moiety to the cytotoxic activity, three series of novel quinazolin-4(3H)-one derivatives b...

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Published inMedicinal chemistry (Shp-sariqah, United Arab Emirates) Vol. 8; no. 2; p. 163
Main Authors Cao, Sheng-Li, Xu, Hong, Wang, Yao, Liao, Ji, Zhang, Jing-Jing, Li, Zhong-Feng, Guo, Yan-Wen, Li, Xiao-Rong, Cui, Xue-Mei, Xu, Xingzhi
Format Journal Article
LanguageEnglish
Published Netherlands 01.03.2012
Subjects
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antineoplastic Agents - toxicity
Cell Line, Tumor
Cell Proliferation - drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
HeLa Cells
HT29 Cells
Humans
Molecular Structure
Quinazolinones - chemical synthesis
Quinazolinones - chemistry
Quinazolinones - pharmacology
Quinazolinones - toxicity
Structure-Activity Relationship
Thiocarbamates - chemistry
Thiocarbamates - pharmacology
Thiourea - chemistry
Thiourea - pharmacology
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Summary:We have previously found that the dithiocarbamate derivatives of quinazolin-4(3H)-one could act as cytotoxic agents against a panel of human tumor cell lines. To investigate the contribution of dithiocarbamate moiety to the cytotoxic activity, three series of novel quinazolin-4(3H)-one derivatives bearing thiocarbamate, thiourea or Nmethyldithiocarbamate side chains were synthesized and tested for their cytotoxic activity against human cancer cell lines A549, MCF-7, HeLa, HT29 and HCT-116 by MTT assay. The results showed that transformation of the dithiocarbamate moiety in lead compound I to thiocarbamate or thiourea led to a decrease or loss of cytotoxic activity. Some N-alkylated analogs of lead compound II preferentially inhibited the proliferation of A549 cells, although their potencies were not improved in comparison with the unalkylated counterparts. The structure-activity relationship obtained in this research will be beneficial for further synthesis and discovery of effective cytotoxic agents.
ISSN:1875-6638
DOI:10.2174/157340612800493665