Synthesis and Anticancer Activity of Some New Fused Pyrazoles and Their Glycoside Derivatives

4‐(4‐Chlorobenzylidene)‐2,5‐diphenyl‐2,3‐dihydro‐3H‐pyrazol‐3‐one 3a and 4‐(3,4‐dimethoxybenzylidene)‐5‐phenyl‐2,3‐dihydro‐3H‐pyrazol‐3‐one 3b were prepared and were reacted with phenylhydrazine, thiosemicarbazide, hydroxylamine hydrochloride, ethyl acetoacetate, diethylmalonate, malononitrile, ethy...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2018-07, Vol.55 (7), p.1709-1719
Main Authors: Nassar, Ibrahim F., El Farargy, Ahmed F., Abdelrazek, Fathy M.
Format: Article
Language:English
Subjects:
Anticancer properties
Breast cancer
Cancer
Doxorubicin
Malononitrile
Pyrazole
Sugar
Thiourea derivatives
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Summary:4‐(4‐Chlorobenzylidene)‐2,5‐diphenyl‐2,3‐dihydro‐3H‐pyrazol‐3‐one 3a and 4‐(3,4‐dimethoxybenzylidene)‐5‐phenyl‐2,3‐dihydro‐3H‐pyrazol‐3‐one 3b were prepared and were reacted with phenylhydrazine, thiosemicarbazide, hydroxylamine hydrochloride, ethyl acetoacetate, diethylmalonate, malononitrile, ethyl cyanoacetate, and thiourea yielding fused pyrazole derivatives. Some of the new compounds were reacted with cyclic and acyclic sugars to produce new S‐, O‐, and N‐glycoside derivatives. The antitumor activity against the human breast cancer cells (MCF‐7) was assessed. Four of the new compounds showed IC50 values less than those of the positive control, indicating that these four compounds are better anticancer agents than doxorubicin.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3208