A novel methodology for synthesis of dihydropyrazole derivatives as potential anticancer agents

A novel, simple, and efficient method for the synthesis of 4,5-dihydropyrazole derivatives has been developed. The reaction proceeded through the base-induced isomerization of easily accessible propargyl alcohols followed by cyclization of alpha,beta-unsaturated hydrazones. Furthermore, selected com...

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Published inOrganic & biomolecular chemistry Vol. 12; no. 13; pp. 2028 - 2032
Main Authors Wang, Xu, Pan, Ying-ming, Huang, Xiao-chao, Mao, Zhong-yuan, Wang, Heng-shan
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.04.2014
Subjects
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Cell Line, Tumor
Cell Proliferation - drug effects
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Hep G2 Cells
Humans
Models, Molecular
Molecular Structure
Physical Sciences
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Pyrazoles - pharmacology
Science & Technology
Structure-Activity Relationship
PYRAZOLINE DERIVATIVES
INHIBITION
RECEPTOR ANTAGONISTS
ANTIBACTERIAL ACTIVITY
4,5-DIHYDROPYRAZOLE
HYDRAZINES
ALDEHYDES
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Summary:A novel, simple, and efficient method for the synthesis of 4,5-dihydropyrazole derivatives has been developed. The reaction proceeded through the base-induced isomerization of easily accessible propargyl alcohols followed by cyclization of alpha,beta-unsaturated hydrazones. Furthermore, selected compounds 3ab and 3ac exhibited good activities against Bel-7404 (human hepatoma cancer), HepG2 (human liver cancer), NCI-H460 (human lung cancer) and SKOV3 (human ovarian cancer) cell lines with IC50 in the range of 22-46 mu mol L-1.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob42432d