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Search for Biologically Active Substances with Antimicrobial and Antifungal Action in the Series of 2.5-Disubstituted 1, 3, 4-Tiadiazoles


Affiliations
1 Department of Medicinal Chemistry, National University of Pharmacy, 53, Pushkinskaya St., Kharkiv, Ukraine
2 Department of General, Bioinorganic, Physical and Colloidal Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska str. 69, Lviv, 79010, Ukraine
     

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A range of derivatives of sulfonyl-substituted nitrogen-containing heterocyclic systems has been extended by synthesis of 2N (R)-5R1-1,3,4-thiadiazol-2-yl-arylsulfonamides and N-(diethylsulfamoyl)-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzamides. It was established that acylation of 5-ethylsulfanyl-1,3,4-thiadiazole-2-amine by heteryl-substituted acid chlorides allowed for obtaining not reported in the literature heterocyclic compounds, which structure contained two cycles of 1,3,4-thiadiazole. The structure and purity of the obtained compounds was confirmed by 1Н NMR-spectroscopy, elemental analysis, and thin-layer chromatography. Pharmacological studies on antimicrobial and antifungal activity have shown that all the compounds tested have sensitivity to both Gram-positive, and Gram-negative bacteria. In addition, the obtained substances have exhibited antifungal activity against Candida albicans. The studies have identified compound 4-butoxy-N-{5-[({[5- (ethylsulfanyl)-1,3,4-thiadiazol-2-yl] carbomoyl} methyl) sulfanyl] -1,3,4-thiadiazol-2-yl} benzamide with high antimicrobial activity further studies of which are promising.

Keywords

Synthesis, 2.5-Disubstituted 1, 3, 4-Tiadiazoles, Antibacterial and Antifungal Activity.
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  • Search for Biologically Active Substances with Antimicrobial and Antifungal Action in the Series of 2.5-Disubstituted 1, 3, 4-Tiadiazoles

Abstract Views: 360  |  PDF Views: 0

Authors

Igor V. Sych
Department of Medicinal Chemistry, National University of Pharmacy, 53, Pushkinskaya St., Kharkiv, Ukraine
Iryna V. Drapak
Department of General, Bioinorganic, Physical and Colloidal Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska str. 69, Lviv, 79010, Ukraine
Marharyta M. Suleiman
Department of Medicinal Chemistry, National University of Pharmacy, 53, Pushkinskaya St., Kharkiv, Ukraine
Maryna V. Rakhimova
Department of Medicinal Chemistry, National University of Pharmacy, 53, Pushkinskaya St., Kharkiv, Ukraine
Natalya P. Kobzar
Department of Medicinal Chemistry, National University of Pharmacy, 53, Pushkinskaya St., Kharkiv, Ukraine
Irina A. Sych
Department of Medicinal Chemistry, National University of Pharmacy, 53, Pushkinskaya St., Kharkiv, Ukraine
Lina O. Perekhoda
Department of Medicinal Chemistry, National University of Pharmacy, 53, Pushkinskaya St., Kharkiv, Ukraine

Abstract


A range of derivatives of sulfonyl-substituted nitrogen-containing heterocyclic systems has been extended by synthesis of 2N (R)-5R1-1,3,4-thiadiazol-2-yl-arylsulfonamides and N-(diethylsulfamoyl)-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzamides. It was established that acylation of 5-ethylsulfanyl-1,3,4-thiadiazole-2-amine by heteryl-substituted acid chlorides allowed for obtaining not reported in the literature heterocyclic compounds, which structure contained two cycles of 1,3,4-thiadiazole. The structure and purity of the obtained compounds was confirmed by 1Н NMR-spectroscopy, elemental analysis, and thin-layer chromatography. Pharmacological studies on antimicrobial and antifungal activity have shown that all the compounds tested have sensitivity to both Gram-positive, and Gram-negative bacteria. In addition, the obtained substances have exhibited antifungal activity against Candida albicans. The studies have identified compound 4-butoxy-N-{5-[({[5- (ethylsulfanyl)-1,3,4-thiadiazol-2-yl] carbomoyl} methyl) sulfanyl] -1,3,4-thiadiazol-2-yl} benzamide with high antimicrobial activity further studies of which are promising.

Keywords


Synthesis, 2.5-Disubstituted 1, 3, 4-Tiadiazoles, Antibacterial and Antifungal Activity.

References