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A series of 1,3-imidazoles and triazole-3-thiones based thiophene-2-carboxamides as anticancer agents: Synthesis and anticancer activity
Reda Ahmed Haggam (1,*)
, Mohamed Gomma Assy (2) , Mohamed Hassan Sherif (3) , Mohamed Mohamed Galahom (4) (1) Department of Chemistry, Faculty of Science, Islamic University in Madinah, Madinah, 42351, Kingdom of Saudi Arabia
(2) Department of Chemistry, Faculty of Science, University of Zagazig, Zagazig, 44519, Egypt
(3) Department of Chemistry, Faculty of Science, University of Zagazig, Zagazig, 44519, Egypt
(4) Department of Chemistry, Faculty of Science, University of Zagazig, Zagazig, 44519, Egypt
(*) Corresponding Author
Received: 18 Mar 2018 | Revised: 08 Apr 2018 | Accepted: 16 Apr 2018 | Published: 30 Jun 2018 | Issue Date: June 2018
Abstract
By addition of semicarbazide or phenylhydrazine hydrochloride to thienoylisothiocyanate (1) resulted in building of thiosemicarbazide derivative (2), triazole derivative (4) and thiophene-2-carboxamide (5), respectively. Basic cyclization of compound 2 led to formation of oxadiazine (3). Synthesis of thiadiazine derivative (6) was achieved via reaction of compound 5 and maleic anhydride in triethyl amine. Heating of compound 5 with ethyl chloroacetate or sodium ethoxide produced thiadiazine derivative (7) and triazolethione (8), respectively. Thiosemicarbazide derivative 11 was synthesized by addition of nicotinic hydrazide to compound 1. Refluxing of compound 11 with lead acetate afforded triazole (13). Moreover, acid and base mediated cyclizations of compound 11 gave thiadiazole (12) and 1,2,4-triazolethione (14) throughout thiophene intermediate, respectively. Addition of ethyl 2-aminothiophene-3-carboxylate to compound 1 formed thiourea (15) which was refluxed with ethoxide giving thiophene-3-carboxylic acid (16). Lastly, nucleophilic addition of amino phenol or ethylene diamine to compound 1 yielded oxazine structure (18) and imidazole derivative (19), respectively. The yields of the synthesized compounds were 61-95%. The detailed synthesis and spectroscopic data of the new compounds are reported.
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DOI: 10.5155/eurjchem.9.2.99-106.1701
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Citations
[1]. E. O. Hamed, M. G. Assy, M. M. Galahom
Heterocyclization of Aromatic Amino Acids: Novel Syntheses and Antibacterial Activity of Fused, Non-fused, and Spiro Polyheterocyclic Derivatives
Russian Journal of Organic Chemistry 56(6), 1062, 2020
DOI: 10.1134/S1070428020060159
[2]. Yu Han, Wei Dong, Qunqun Guo, Xiufen Li, Longjiang Huang
The importance of indole and azaindole scaffold in the development of antitumor agents
European Journal of Medicinal Chemistry 203, 112506, 2020
DOI: 10.1016/j.ejmech.2020.112506
[3]. Reda A. Haggam, Essam. A. Soylem, Mohamed. G. Assy, Marium. F. Arastiedy
Synthesis and antimicrobial evaluation of new series of quinazolin-5-one derivatives
Journal of the Iranian Chemical Society 17(7), 1715, 2020
DOI: 10.1007/s13738-020-01896-0
[4]. R. A. Haggam, H. Y. Moustafa, M. G. Assy, H. M. Abd El-Rahman
One-Pot Multicomponent Synthesis and Anticancer Activity of 1,3-Cyclopentathiazine and Pyrimidothiazine Derivatives
Russian Journal of Organic Chemistry 56(5), 916, 2020
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[5]. Neha V. Bhilare, Pratibha B. Auti, Vinayak S. Marulkar, Vilas J. Pise
Diverse Thiophenes as Scaffolds in Anti-cancer Drug Development: A Concise Review
Mini-Reviews in Medicinal Chemistry 21(2), 217, 2021
DOI: 10.2174/1389557520666201202113333
[6]. Reda A. Haggam
Microwave-assisted synthesis of double-headed derivatives of (4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-ethan-1-ol and study of their biological activity
Research on Chemical Intermediates 47(9), 3733, 2021
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[7]. Alexei N. Izmest’ev, Andrey А. Streltsov, Angelina N. Kravchenko, Galina А. Gazieva
The Chemo- and Regioselectivity of the Cyclization of Thiosemicarbazides with Haloacetic Acids and their Derivatives
Chemistry of Heterocyclic Compounds 58(10), 483, 2022
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DOI Link: https://doi.org/10.5155/eurjchem.9.2.99-106.1701
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European Journal of Chemistry 2018, 9(2), 99-106 | doi: https://doi.org/10.5155/eurjchem.9.2.99-106.1701 | Get rights and content
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