The synthesis and the antimicrobial activity of N1-substituted 5-amino-4-arylsulfonyl-3-N-phenylaminopyrazoles

P. V. Tkachenko, O. V. Tkachenko, K. Yu. Netosova, O. V. Borisov, I. O. Zhuravel, V. V. Kazmirchuk

Abstract


This article is continuation of the development of methods for the synthesis of small molecules based on the structure of 5-aminopyrazole. The synthesis and the antimicrobial activity for a series of new N1-subsituted 5-amino-4-arylsulfonyl-3-N-phenylaminopyrazoles have been described.
Aim. To synthesize derivatives of 5-amino-4-arylsulfonyl-3phenylaminopyrazoles and study their antimicrobial and antifungal properties.
Materials and methods. The methods of organic synthesis, instrumental methods of organic compounds analysis and methods of microbiological screening were used.
Results and discussion. 5-Amino-4-arylsulfonyl-3-phenylaminopyrazoles were prepared by the reaction of arylsulfonylacetonitriles with isothiocyanates in the presence of NaOH and CH3I with further cyclization with hydrazine hydrate. The reaction of this compounds with N-arylchloroacetamides finished a series of N1-substituted 5-amino-4-arylsulfonyl-3-phenylaminopyrazoles. The antibacterial and antifungal properties of the compounds synthesized were studied. Some of the compounds obtained appeared to be potent inhibitors for several pathogenic bacterial and fungal lines.
Conclusions. The synthetic scheme for obtaining of N1-substituted 5-amino-4-arylsulfonyl-3-phenylaminopyrazoles, which can be used for creation of a library of compounds for in vitro antimicrobial screening, has been proposed. Some of the compounds synthesized are of certain interest as potential pharmaceutical agents and can be used to develop new antifungal agents.


Keywords


5-aminopyrazole; synthesis; antimicrobial activity; antifungal activity

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DOI: https://doi.org/10.24959/nphj.17.2159

Abbreviated key title: Vìsn. farm.

ISSN 2415-8844 (Online), ISSN 1562-7241 (Print)