The synthesis of the substituted 4-alkyl/arylsulfonyl-5-amino-3-alkylthiopyrazoles as promising pharmaceutical agents with the antifungal action

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

Abstract


One of the promising directions for development of antifungal agents is the synthesis of new chemical compounds that can be used as active pharmaceutical ingredients to produce highly effective drugs for the treatment of fungal infestations.

Aim. To create the combinatorial library of 4-alkyl/arylsulfonyl-5-amino-3-alkylthiopyrazoles derivatives for the total antimicrobial screening to search for new substances with the antifungal activity, and study their spectral properties.

Materials and methods. The methods of organic synthesis, instrumental methods of organic compound analysis were used.

Results and discussion. The design of the library of small molecules based on the core structure of 5-aminopirazole has been developed. The useful and effective synthetic scheme for preparing N1-subsituted 4-alkyl/arylsulfonyl-5-amino-3-alkylthiopyrazoles and their acylation products has been proposed and approved. This approach consists of cyclization of substituted alkyl/arylsulfoacetonitriles under the action of hydrazine hydrate with further alkylation and acylation of 5-aminopyrazoles obtained. The total yield of the target products is 50-85 %. The structure of all compounds synthesized has been confirmed using elemental analysis, 1H NMR- and chromato-mass spectrometric methods.

Conclusions. The design and the synthetic scheme for obtaining 4-alkyl/arylsulfonyl-5-amino-3-alkiltiopirazoles and products of their chemical modification have been proposed. The compounds synthesized are of certain interest as potential pharmaceutical agents and can be used to develop new antifungal agents.


Keywords


pyrazole; combinatorial library; synthesis; pharmaceutical agents

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References


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GOST Style Citations


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DOI: https://doi.org/10.24959/nphj.17.2158

Abbreviated key title: Vìsn. farm.

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