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Synthesis and antitumor activity evaluation of some pyrrolone and pyridazinone heterocycles derived from 3-((2-oxo-5-( <i>p</i> -tolyl)furan-3(2 <i>H</i> )-ylidene)methyl)quinolin-2(1 <i>H</i> )-one

Eman A. E. El‐Helw, Ahmed I. Hashem

2020Synthetic Communications28 citationsDOI

Abstract

The broad spectrum of biological activity of quinoline derivatives coupled with our interest in the chemistry of furanones led us to synthesize a quinoline derivative bearing a 2(3H)-furanone scaffold. This derivative was used as a key starting material for the construction of some pyrrolone, imidazole, and pyridazinone derivatives obtained by reactions with some nitrogen nucleophiles viz. ammonium acetate, benzylamine, 1,2-diaminoethane, and hydrazine hydrate. The hydrazide obtained was condensed with 3-chlorobenzaldehyde, 1,3-diphenyl-1H-pyrazole-4-carbaldehyde, isatin, and dodecanoyl chloride to achieve the corresponding hydrazone and pyrrolone derivatives. Also, the synthesized compounds were evaluated for their in vitro antitumor activity using two cancer cell lines: breast and colon tumors. Some compounds displayed satisfactory activities.

Topics & Concepts

ChemistryHydrazine (antidepressant)IsatinQuinolineHydrazoneHydrazideMethylamineImidazolePyrazoleFuranBenzylamineAmmonium acetateNucleophileMedicinal chemistryDerivative (finance)HydroxylamineCombinatorial chemistryOrganic chemistryCatalysisFinancial economicsChromatographyHigh-performance liquid chromatographyEconomicsSynthesis of Organic CompoundsSynthesis and biological activityOrganic Chemistry Synthesis Methods
Synthesis and antitumor activity evaluation of some pyrrolone and pyridazinone heterocycles derived from 3-((2-oxo-5-( <i>p</i> -tolyl)furan-3(2 <i>H</i> )-ylidene)methyl)quinolin-2(1 <i>H</i> )-one | Litcius