A series of 1,3-imidazoles and triazole-3-thiones based thiophene-2-carboxamides as anticancer agents: Synthesis and anticancer activity
Open Access
- 30 June 2018
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 9 (2), 99-106
- https://doi.org/10.5155/eurjchem.9.2.99-106.1701
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
This publication has 23 references indexed in Scilit:
- Biological approach of anticancer activity of new benzimidazole derivativesPharmacological Reports, 2014
- Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivativesEuropean Journal of Medicinal Chemistry, 2010
- Synthesis and biological evaluation of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives as antidepressant, anxiolytics and anticonvulsant agentsMedicinal Chemistry Research, 2010
- Identification of 1-isopropylsulfonyl-2-amine benzimidazoles as a new class of inhibitors of hepatitis B virusEuropean Journal of Medicinal Chemistry, 2007
- Synthesis and inhibitory activity of new benzimidazole derivatives against Burkitt’s lymphoma promotionBioorganic & Medicinal Chemistry, 2007
- Synthesis of Novel Derivatives of 4-Amino-3-(2-Furyl)-5-Mercapto-1,2,4-Triazole as Potential HIV-1 NNRTIsMolecules, 2007
- Generation of potent coagulation protease inhibitors utilizing zinc-mediated chelationBioorganic & Medicinal Chemistry Letters, 2006
- Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazolesEuropean Journal of Medicinal Chemistry, 2003
- Synthesis, structural characterization, crystallographic analysis and antibacterial properties of some nitrofuryl triazolo[3,4-b]-1,3,4-thiadiazinesEuropean Journal of Medicinal Chemistry, 1994
- 4‐Amino‐3‐mercapto‐4H‐1,2,4‐triazoles and propargyl aldehydes: A new route to 3‐R‐8‐aryl‐1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazepinesJournal of Heterocyclic Chemistry, 1980