Synthesis and SAR studies of pyrazole-3-carboxamides and -3-carbonyl thioureides including chiral moiety: Novel candidates as antibacterial agents

Main Article Content

Ishak Bildirici
Adnan Cetin
Nurettin Menges
Yusuf Alan

Abstract

A series of tetrasubstituted pyrazole-3-carboxamides (3a–c) and pyr­azole-3-carbonyl thioureides (6ac) were synthesized and their structures char­ac­terized by IR, NMR and elemental analysis. The antibacterial potential against specific Gram-positive and Gram-negative strains and the antifungal activities of all novel compounds were investigated. Structure–activity relation­ships (SAR) studies and some theoretical parameters (ClogP, CMR, PSA and ESP) of the compounds were performed on these two pyrazole derivatives. Pyrazole-3-carboxylate ester 2 was used for the synthesis of the carboxamide derivatives. The reactions of pyrazole-3-carbonyl isothiocyanate 5 with appro­priate chiral amino alco­hols were utilized for synthesizing the thioureide deri­vatives. Both of these types of pyrazole derivatives including a chiral moiety exhibited pronounced antibacterial activities. According to the present in vitro study, some of the pro­mising compounds might be new candidates for a new generation of antibacterial drugs.

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How to Cite
[1]
I. Bildirici, A. Cetin, N. Menges, and Y. Alan, “Synthesis and SAR studies of pyrazole-3-carboxamides and -3-carbonyl thioureides including chiral moiety: Novel candidates as antibacterial agents”, J. Serb. Chem. Soc., vol. 83, no. 7-8, pp. 795–807, Aug. 2018.
Section
Organic Chemistry

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