Synthesis of some novel thiophene analogues as potential anticancer agents

Almatari, Altaf S., Saeed, Ali, Abdel-Ghani, Ghada E., Abdullah, Mahmood M. S., Al-Lohedan, Hamad A., Abdel-Latif, Ehab and El-Demerdash, Amr ORCID: https://orcid.org/0000-0001-6459-2955 (2024) Synthesis of some novel thiophene analogues as potential anticancer agents. Chemistry and Biodiversity, 21 (7). ISSN 1612-1872

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Abstract

The aim of this study involves the synthesis novel thiophene analogues that can be used as anticancer medications through a strategic multicomponent reaction connecting ethyl 4-chloroacetoacetate (1), phenyl isothiocyanate, and a series of active methylene reagents, including ethyl acetoacetate (2), malononitrile, ethyl cyanoacetate, cyanoacetamide 6a–c, N-phenyl cyanoacetamide derivatives 13a–c, and acetoacetanilide derivatives 18. This reaction was facilitated by dry dimethylformamide with a catalytic quantity of K2CO3. The resultant thiophene derivatives were identified as 4, 8a–b, 9, 12a–d, 15a–c, and 20a–b. Further reaction of compound 4 with hydrazine hydrate yielded derivative 5, respectively. When compound 1 was refluxed with ethyl 3-mercapto-3-(phenylamino)-2-(p-substituted phenyldiazenyl)acrylate 10a–e in the presence of sodium ethoxide, it produced thiophene derivatives 12a–d. Comprehensive structural elucidation of these newly synthesized thiophene-analogues was accomplished via elemental and spectral analysis data. Furthermore, the study delves into the cytotoxicity of the newly synthesized thiophenes was evaluated using the HepG2, A2780, and A2780CP cell lines. The amino-thiophene derivative 15b exhibited an increased growth inhibition of A2780, and A2780CP with IC50 values 12±0.17, and 10±0.15 μM, respectively compared to Sorafenib with IC50 values 7.5±0.54 and 9.4±0.14. This research opens new avenues for developing thiophene-based anticancer agents.

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. Publisher Copyright: © 2024 Wiley-VHCA AG, Zurich, Switzerland.
Uncontrolled Keywords:	anticancer activity,ethyl 4-chloroacetoacetate,thieno[3,2-b]pyridine,thiophenes,bioengineering,biochemistry,chemistry(all),molecular medicine,molecular biology ,/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/96201
DOI:	10.1002/cbdv.202400313

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