Synthesis and molecular docking of some new thiazolidinone and thiadiazole derivatives as anticancer agents

Saeed, Ali, Soliman, Ahbarah M., Abdullah, Mahmood M. S., Abdel-Latif, Ehab and El-Demerdash, Amr ORCID: https://orcid.org/0000-0001-6459-2955 (2024) Synthesis and molecular docking of some new thiazolidinone and thiadiazole derivatives as anticancer agents. Chemistry and Biodiversity, 21 (7). ISSN 1612-1872

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Abstract

New sets of functionalized thiazolidinone and thiadiazole derivatives were synthesized, and their cytotoxicity was evaluated on HepG2, MCF-7, HTC-116, and WI38 cells. The synthetic approach is based on the preparation of 4-(4-acetamidophenyl)thiosemicarbazide (4) and their thiosemicarbazones 5 a–e, which are converted to the corresponding thiazoldin-4-one compounds 6 a–e upon cyclization with ethyl bromoacetate. The thiadiazole compounds 9 and 12 were obtained by reacting 4-(4-acetamidophenyl)thiosemicarbazide with isothiocyanates and/or ethyl 2-cyano-3,3-bis(methylthio)acrylate, respectively. The thiazolidinone compounds 6 c and 6 e exhibited strong cytotoxicity against breast cancer cells, with an IC50 (6.70±0.5 μM) and IC50 (7.51±0.8 μM), respectively, very close to that of doxorubicin (IC50: 4.17±0.2 μM). In addition, the anti-cancer properties of the tested thiazolidinone and thiadiazole scaffolds were further explored by the molecular docking program (MOE)-(PDB Code-1DLS). Compounds 5 d, 5 e, 6 d, 6 e, and 7 have the best binding affinity, ranging from −8.5386 kcal.mol−1 to −8.2830 kcal.mol−1.

Item Type:	Article
Additional Information:	Funding Information: The authors acknowledge the financial support through Researchers Supporting Project number (RSPD2024R688), King Saud University, Riyadh, Saudi Arabia. This research was funded by Researchers Supporting Project number (RSPD2024R688), King Saud University, Riyadh, Saudi Arabia.
Uncontrolled Keywords:	4-aminoacetanilide,docking,hepg2,thiadiazole,thiazolidin-4-one,bioengineering,biochemistry,chemistry(all),molecular medicine,molecular biology,sdg 3 - good health and well-being ,/dk/atira/pure/subjectarea/asjc/1500/1502
Faculty \ School:	Faculty of Science > School of Pharmacy (former - to 2024)
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	12 Aug 2024 17:30
Last Modified:	25 Sep 2024 17:58
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96200
DOI:	10.1002/cbdv.202301870

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