Synthesis of some 5‐arylidene‐2‐(4‐acetamidophenylimino)‐thiazolidin‐4‐one derivatives and exploring their breast anticancer activity | Zendy

Abumelha Hana M. A. | Zendy; Saeed Ali | Zendy

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Synthesis of some 5‐arylidene‐2‐(4‐acetamidophenylimino)‐thiazolidin‐4‐one derivatives and exploring their breast anticancer activity

Author(s) -

Abumelha Hana M. A.,

Saeed Ali

Publication year - 2020

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.3906

Subject(s) - chemistry , knoevenagel condensation , ethyl bromoacetate , thiourea , cancer cell lines , ethanol , derivative (finance) , sodium ethoxide , ethyl acetate , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , cancer , cancer cell , medicine , financial economics , economics , catalysis

Ten 2‐(4‐acetamidophenylimino)‐5‐arylidenethiazolidin‐4‐one derivatives 6a‐k were synthesized and evaluated for their anticancer activity against MCF‐7 cell line (breast adenocarcinoma). The synthetic approach involves cyclocondensation of N , N′ ‐bis(4‐acetamidophenyl)‐thiourea (3) with ethyl bromoacetate in ethanol and sodium acetate to furnish the 2‐(4‐acetamidophenylimino)‐4‐thiazolidinone derivative 4 , which underwent Knoevenagel condensation reaction with some substituted aldehydes to afford the targeted 2‐(4‐acetamidophenylimino)‐5‐arylidenethiazolidin‐4‐ones 6a ‐ k . The 4‐chlorobenzylidene‐thiazolidin‐4‐one compound 6h exhibited strong inhibitory effect on the growth of breast cancer cell with IC 50 (58.33 ± 1.74μM), very close to that of the reference drug doxorubicin (IC 50 48.06 ± 0.36μM).

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