New thiophene-1,2,4-triazole-5(3)-ones: Highly bioactive thiosemicarbazides, structures of Schiff bases and triazole–thiols

Jul 27, 2014European journal of medicinal chemistry

New Thiophene-Triazole Compounds: Highly Active Thiosemicarbazides and Structures of Related Schiff Bases and Triazole-Thiols

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Abstract

Thiosemicarbazide derivatives exhibited 69.0-88.2% DPPH· scavenging activity.

New compounds were synthesized from a key precursor involving hydrazine and an ester compound.
The newly formed thiosemicarbazide derivatives demonstrated significant antioxidant properties in multiple tests.
The antioxidant activity of thiosemicarbazide derivatives correlated well across two different evaluation methods.
These derivatives also showed antibacterial effects against several bacterial strains, including Staphylococcus aureus and Bacillus cereus.
The thiosemicarbazide group is highlighted as a promising candidate for developing bioactive compounds.

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Key compound 2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1-yl) acetohydrazide (3) was synthesized by reacting hydrazine hydrate with ethyl-2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1yl)acetate (2), obtained in basic media from 4-amino-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-one (1). Compound 3 was converted to thiosemicarbazide derivatives (4a-d) and Schiff base derivatives 6a-e and 7a-e. The treatment of compound 4 with NaOH gave 4-amino-2-((4-(4-aryl)-5-mercapto-4H-1,2,4-triazole-3-yl)methyl)-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-ones (5a-d). All newly compounds, well characterized by elemental analyses, IR, (1)H NMR, (13)C NMR and mass spectral studies were tested for their antioxidant and antimicrobial activities. Thiosemicarbazide derivatives (4a-d) were highly active in two antioxidant tests with 69.0-88.2% DPPH· scavenging and 503-1257 μM TEAC values, while the others showed lower or no activity. The results of the two antioxidant tests correlated well. Moreover, Thiosemicarbazide derivatives (4a-d) also showed antibacterial activity against Staphylococcus aureus, Bacillus cereus, and Mycobacterium smegmatis. Thiosemicarbazide group deserves attention in the synthesis of bioactive compounds.

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New thiophene-1,2,4-triazole-5(3)-ones: Highly bioactive thiosemicarbazides, structures of Schiff bases and triazole–thiols

Abstract

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