Synthesis and Anticancer Activity of New 2-Aryl-4-(4-Methoxybenzylidene)-5-Oxazolone Scaffolds | Zendy

Ahmed A. Fadda | Zendy; Raaben Mohammed | Zendy; Eman H. Tawfik | Zendy; Mamdouh Hammouda | Zendy

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Synthesis and Anticancer Activity of New 2-Aryl-4-(4-Methoxybenzylidene)-5-Oxazolone Scaffolds

Author(s) -

Ahmed A. Fadda,

Raaben Mohammed,

Eman H. Tawfik,

Mamdouh Hammouda

Publication year - 2020

Publication title -

biointerface research in applied chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.216

H-Index - 11

ISSN - 2069-5837

DOI - 10.33263/briac111.80968109

Subject(s) - oxazolone , chemistry , malononitrile , reagent , aryl , combinatorial chemistry , organic chemistry , alkyl , catalysis

A new series of 4-(4-methoxybenzylidene)-2-substitutedphenyl-5(4H)-oxazolone derivatives has been synthesized through the application of Erlenmeyer condition (Ac2O, AcONa, and 4-anisaldehyde) to the reaction products of the highly versatile p-aminohippuric acid with various electrophilic reagents such as aromatic aldehydes, phenyl isothiocyanate, diazotization-coupling reaction (malononitrile and 2-amino-4-phenylthiazole) and cyanoacetyl-pyrazole. IR, 1H NMR, and mass spectroscopic techniques were utilized to confirm the structures of these oxazolone scaffolds. The synthesized oxazolone derivatives were evaluated against four human cancer cell lines (HepG2, HTC-116, PC-3, and MCF-7). Compound 3e showed the best activity against hepatocellular carcinoma (IC50 8.9±0.30 μg/mL) and colorectal carcinoma (IC50 9.2±0.63 μg/mL) cell lines compared with the standard anticancer drug 5-fluorouracil.

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