Synthesis and Biological Properties of Novel Triazole-Thiol and Thiadiazole Derivatives of the 1,2,4-Triazole-3(5)-one Class

Esra Düğdü,Dilek Ünlüer,Yasemin Ünver,Kemal Sancak

doi:10.3390/molecules19022199

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https://doi.org/10.3390/molecules19022199

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Journal: Molecules (Basel, Switzerland)	Publication Date: Feb 19, 2014
Citations: 26	License type: CC BY 4.0

Affiliation: Karadeniz Technical University

Abstract

2,2'-(4,4'(Butane-1,4-diyl/hexane-1,6-diyl)bis(3-methyl-5-oxo-4,5-dihydro-1,2,4-triazole-4,1-diyl)) diacetohydrazides 3a,b were obtained via the formation of diethyl 2,2'-(4,4'(butane-1,4-diyl/hexane-1,6-diyl)bis(3-methyl-5-oxo-4,5-dihydro-1,2,4-triazole-4,1-diyl))diacetates 2a,b, obtained starting from di-[3(methyl-2-yl-methyl)-4,5-dihydro-1H-[1,2,4]-triazole-5-one-4yl]-n-alkanes 1a,b in two steps. The synthesis of the compounds 7a,b–9a,b incorporating the 1,3,4-thiadiazole, and 10a,b–11a,b with a 1,2,4-triazole-thiol nucleus as the second heterocycle, was performed by the acidic or basic treatment of compounds 4a,b–6a,b which were obtained from the reaction of 3a,b with several isothiocyanates. Newly synthesized compounds were screened for antimicrobial activities and their antioxidant properties by the 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging method. Compounds 4a,b, 5a,b, and 6a,b were found to possess good antioxidant properties. Almost all compounds have significant antimicrobial activities.

Highlights

Derivatives of 1,3,4-thiadiazoles and 1,2,4-triazole are known to exhibit anti-inflammatory, antiviral, analgesic, antimicrobial, anticonvulsant and antidepressant activity, the latter being usually explored by the forced swim test [1,2,3,4,5,6,7,8,9,10]
Heterocycles containing a 1,2,4-triazole or 1,3,4-thiadiazole moiety, and the compounds consisting of 1,2,4-triazole and 1,3,4-thiadiazole condensed nucleus systems constitute a class of compounds possessing a wide spectrum of biological activities such as anti-inflammatory, antiviral and antimicrobial and antitumoral properties [12,13,14,15,16,17,18]
Keeping this observation in mind, this paper has presented the synthesis of new triazole thiadiazole derivatives incorporating different pharmacophores as hybrid molecules possessing antioxidant and antimicrobial activities [19]

Summary

Introduction

Derivatives of 1,3,4-thiadiazoles and 1,2,4-triazole are known to exhibit anti-inflammatory, antiviral, analgesic, antimicrobial, anticonvulsant and antidepressant activity, the latter being usually explored by the forced swim test [1,2,3,4,5,6,7,8,9,10]. Heterocycles containing a 1,2,4-triazole or 1,3,4-thiadiazole moiety, and the compounds consisting of 1,2,4-triazole and 1,3,4-thiadiazole condensed nucleus systems constitute a class of compounds possessing a wide spectrum of biological activities such as anti-inflammatory, antiviral and antimicrobial and antitumoral properties [12,13,14,15,16,17,18]. It was reported that more efficacious antibacterial compounds can be designed by joining two or more biologically active heterocyclic systems together in a single molecular framework. Keeping this observation in mind, this paper has presented the synthesis of new triazole thiadiazole derivatives incorporating different pharmacophores as hybrid molecules possessing antioxidant and antimicrobial activities [19]

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