Abstract
This article describes the synthesis of some novel heterocyclic sulfonamides having biologically active thiophene 3, 4, 5, 6, coumarin 8, benzocoumarin 9, thiazole 7, piperidine 10, pyrrolidine 11, pyrazole 14 and pyridine 12, 13. Starting with 4-(1-(2-(2-cyanoacetyl)hydrazono)ethyl)-N-ethyl-N-methylbenzenesulfonamide (2), which was prepared from condensation of acetophenone derivative 1 with 2-cyanoacetohydrazide. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1H NMR, 13C NMR, 19F NMR and MS spectral data. All the newly synthesized heterocyclic sulfonamides were evaluated as in-vitro anti-breast cancer cell line (MCF7) and as in-vitro antimicrobial agents. Compounds 8, 5 and 11 were more active than MTX reference drug and compounds 12, 7, 4, 14, 5 and 8 were highly potent against Klebsiella pneumonia. Molecular operating environment performed virtual screening using molecular docking studies of the synthesized compounds. The results indicated that some prepared compounds are suitable inhibitor against dihydrofolate reductase (DHFR) enzyme (PDBSD:4DFR) with further modification.
Highlights
One of the most important and desirable field in medicinal chemistry, is to find a new specific anticancer agents and to develop new safer, potent and resistance-free antimicrobial drugs. It is evident from the literature survey that benzenesulfonamides exhibited a significant anticancer and antimicrobial activity[1,2,3,4]
Benzenesulfonamides derivatives having aromatic heterocyclic moiety possess a wide spectrum of pharmacological activities, such as anticancer[5,6,7], anti-bacterial[8,9,10], anti-inflammatory[11] and anti-viral[12], hypoglycemic[13], diuretic[14,15], anticarbonic anhydrase[16] and anti-thyroid[17], antimalarial[18] and antileprotic[19,20] activity
The reaction of 4-(1-(2-(2-cyanoacetyl)hydrazono)ethyl)-N-ethyl-Nmethylbenzenesulfonamide (2) with diethyl malonate in the presence of trimethylamine gave the corresponding piperidine derivative 10
Summary
One of the most important and desirable field in medicinal chemistry, is to find a new specific anticancer agents and to develop new safer, potent and resistance-free antimicrobial drugs. The b-functional nitrile[1,2,3,4] moiety of the molecule is a favorable unit for addition followed by cyclization or via cycloaddition with numerous reagents providing heterocyclic compounds of different ring sizes with one or several heteroatoms that are interesting as pharmaceuticals agents[24,25,26,27,28,29,30] Considering this background, some novel heterocyclic sulfonamides as thiophenes [3, 4, 5] and 6, thiazole 7, chromenes 8 and 9, piperidine 10, pyrrolidine 11, tetrahydropyridine 12, pyridine 13, pyrazole and hydrazono derivatives were prepared and tested in terms of anticancer and antimicrobial activity with the purpose of revealing possible leading compounds for development of new anticancer and antimicrobial agents
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