European Journal of Chemistry 2018, 9(2), 99-106. doi:10.5155/eurjchem.9.2.99-106.1701

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,*) orcid , 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, Accepted: 16 Apr 2018, Published: 30 Jun 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.


Keywords


Thiophene; 1,3-Imidazole; Isothiocyanates; 1,3,4-Thiadiazoles; Triazole-3-thiones; Anticancer activity

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DOI: 10.5155/eurjchem.9.2.99-106.1701

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How to cite


Haggam, R.; Assy, M.; Sherif, M.; Galahom, M. Eur. J. Chem. 2018, 9(2), 99-106. doi:10.5155/eurjchem.9.2.99-106.1701
Haggam, R.; Assy, M.; Sherif, M.; Galahom, M. A series of 1,3-imidazoles and triazole-3-thiones based thiophene-2-carboxamides as anticancer agents: Synthesis and anticancer activity. Eur. J. Chem. 2018, 9(2), 99-106. doi:10.5155/eurjchem.9.2.99-106.1701
Haggam, R., Assy, M., Sherif, M., & Galahom, M. (2018). A series of 1,3-imidazoles and triazole-3-thiones based thiophene-2-carboxamides as anticancer agents: Synthesis and anticancer activity. European Journal of Chemistry, 9(2), 99-106. doi:10.5155/eurjchem.9.2.99-106.1701
Haggam, Reda, Mohamed Gomma Assy, Mohamed Hassan Sherif, & Mohamed Mohamed Galahom. "A series of 1,3-imidazoles and triazole-3-thiones based thiophene-2-carboxamides as anticancer agents: Synthesis and anticancer activity." European Journal of Chemistry [Online], 9.2 (2018): 99-106. Web. 15 Nov. 2019
Haggam, Reda, Assy, Mohamed, Sherif, Mohamed, AND Galahom, Mohamed. "A series of 1,3-imidazoles and triazole-3-thiones based thiophene-2-carboxamides as anticancer agents: Synthesis and anticancer activity" European Journal of Chemistry [Online], Volume 9 Number 2 (30 June 2018)

DOI Link: https://doi.org/10.5155/eurjchem.9.2.99-106.1701

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