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ScienceRise: Pharmaceutical Science
Article . 2017 . Peer-reviewed
Data sources: Crossref
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ScienceRise: Pharmaceutical Science
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License: CC BY
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Products of interaction of substituted 5-aminopyrazoles with α -haloketones as potential pharmaceutical agents

Authors: Tkachenko, Pavlo; Tkachenko, Olena; Netosova, Krystyna; Borisov, Oleksandr; Zhuravel, Iryna;

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

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 N 1 -alkylation products, in this reaction a mixture of N 1 - and N 2 -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 N 1 -alkylation of 5-aminopyrazoles 1a-b and the cyclization of products 2 in imidazo[1,2-b]pyrazoles 4a-c without isolating the N 2 -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

Keywords

pyrazole; -haloketones; 1H-imidazo[1;2-b]pyrazoles; synthesis; alkylation; pharmaceutical agents; NMR spectroscopy; isomerism, піразол; -галогенокетони; 1H-імідазо[1;2-b]піразоли; синтез; алкілування; фармацевтичний агент; 1H ЯМР-спектроскопія; ізомерія, UDC 54.057:547.77:547-302:547-316

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
0
Average
Average
Average
gold