Products of interaction of substituted 5-aminopyrazoles with α -haloketones as potential pharmaceutical agents

Authors

DOI:

https://doi.org/10.15587/2519-4852.2017.113493

Keywords:

pyrazole, -haloketones, 1H-imidazo[1, 2-b]pyrazoles, synthesis, alkylation, pharmaceutical agents, NMR spectroscopy, isomerism

Abstract

Aim. Optimization of reaction of substituted 5-aminopyrazoles with a-haloketones to form annealed 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles.

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

Results. A scheme for the synthesis of 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles by the interaction of 5-amino-4-arylsulfonyl-3-methylthiopyrazoles 1a-b with chloroacetone, phenacyl bromide and 2-chlorocyclohexanone was developed. In contrast to the previously described interaction of substituted 5-aminopyrazoles with chloro (N-aryl) acetamides proceeding exclusively with the release of N1-alkylation products, in this reaction a mixture of N1- and N2-isomeric alkylation products is formed. The ratio of isomers depends on the nature of the reagents and, according to the 1H NMR-spectroscopy, is about 60:40 %.The developed technique allows with one of the synthetic procedure to carry out N1-alkylation of 5-aminopyrazoles 1a-b and the cyclization of products 2 in imidazo[1,2-b]pyrazoles 4a-c without isolating the N2-alkylation product. The purity of the obtained compounds is proved chromatographically, the structure is confirmed by the data of 1H NMR-spectroscopy.

Conclusions. Optimized reaction of substituted 5-aminopyrazoles with a-haloketones to form annealed 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles for targeted synthesis of the novel agents for the pharmaceutical practice

Author Biographies

Pavlo Tkachenko, National University of Pharmacy Pushkinska str., 53, Kharkiv, Ukraine, 61002

Postgraduate student

Department of Drug and Analytical Toxicology

Olena Tkachenko, National University of Pharmacy Pushkinska str., 53, Kharkiv, Ukraine, 61002

PhD, Associate Professor

Department of Quality Management

Krystyna Netosova, National University of Pharmacy Pushkinska str., 53, Kharkiv, Ukraine, 61002

PhD, Assistant

Department of Drug and Analytical Toxicology

Oleksandr Borisov, LLC “RPE “Enamine” Chervonotkatska str., 78, Kyiv, Ukraine, 02660

PhD, Head of Laboratory 

Iryna Zhuravel, Kharkiv Medical Academy of Post-graduate Education Amosova str., 58, Kharkiv, Ukraine, 61176

Doctor of Chemical Sciences, Professor

Department of Clinical Biochemistry, Forensic Toxicology and Pharmacy

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Published

2017-10-31

How to Cite

Tkachenko, P., Tkachenko, O., Netosova, K., Borisov, O., & Zhuravel, I. (2017). Products of interaction of substituted 5-aminopyrazoles with α -haloketones as potential pharmaceutical agents. ScienceRise: Pharmaceutical Science, (5 (9), 25–28. https://doi.org/10.15587/2519-4852.2017.113493

Issue

No. 5 (9) (2017)

Section

Pharmaceutical Science

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Copyright (c) 2017 Pavlo Tkachenko, Olena Tkachenko, Krystyna Netosova, Oleksandr Borisov, Iryna Zhuravel

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