Facile synthesis and antimicrobial evaluation of some new heterocyclic compounds incorporating a biologically active sulfamoyl moiety.

Elham S Darwish

doi:10.1155/2014/165495

Abstract

A facile and convenient synthesis of new heterocyclic compounds containing a sulfamoyl moiety suitable for use as antimicrobial agents was reported. The precursor 3-oxo-3-phenyl-N-(4-sulfamoylphenyl)propionamide was coupled smoothly with arenediazonium salt producing hydrazones which reacted with malononitrile or triethylorthoformate affording pyridazine and triazine derivatives, respectively. Also, the reactivity of the same precursor with DMF-DMA was followed by aminotriazole; aromatic aldehydes was followed by hydrazine hydrate, triethylorthoformate, or thiourea affording triazolo[1,5-a]pyrimidine, pyrazole, acrylamide, and dihydropyrimidine derivatives, respectively. On the other hand, treatment of the precursor propionamide with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt which was treated with dilute HCl followed by 2-bromo-1-phenylethanone affording carboxamide derivative. While the same intermediate salt reacted in situ with chloroacetone, ethyl 2-chloroacetate, 3-(2-bromoacetyl)-2H-chromen-2-one, methyl iodide, or 2-oxo-N-phenylpropane hydrazonoyl chloride afforded the thiophene, ketene N,S-acetal, and thiadiazole derivatives, respectively. The structure of the new products was established based on elemental and spectral analysis. Antimicrobial evaluation of some selected examples from the synthesized products was carried out whereby four compounds were found to have moderate activities and one compound showed the highest activity.

Highlights

Sulfonamides have been reported to exhibit antimicrobial [1,2,3], antifungal [4], insulin releasing [5], carbonic anhydrase inhibitory [6], anti-inflammatory [7], and antitumor [8], properties
Some active sulfonamides as antibacterial are known for their immune modifying effects [9]
Results from assessment of the antimicrobial activity of these newly synthesized compounds are reported in this study

Summary

Introduction

Sulfonamides have been reported to exhibit antimicrobial [1,2,3], antifungal [4], insulin releasing [5], carbonic anhydrase inhibitory [6], anti-inflammatory [7], and antitumor [8], properties. Thiophene compounds are well known to exhibit various biological and medicinal activities such as BACEI inhibitors [16], antitubercular [17], antidepressant [18], antiinflammatory [19], and anti-HIV PR inhibitors [20], and antibreast cancer activities [21] These facts, coupled with our desire to develop efficacious antimicrobial agents, and in continuation of our work in heterocycles of biological interest [22,23,24,25], prompted us to devise an efficient and convenient method of synthesis of hitherto unknown and novel hydrazone, pyridazine, acrylamide, pyrazole, triazolo[1,5a]pyrimidine, thiadiazole, dihydropyrimidine, and thiophene derivatives with a sulfonamide nucleus. Results from assessment of the antimicrobial activity of these newly synthesized compounds are reported in this study

Experimental Part

Results and Discussion

Conclusions