Synthesis and Antimicrobial Evaluation of Novel Pyrazolopyrimidines Incorporated with Mono- and Diphenylsulfonyl Groups.

Alsaedi Alsaedi,Farghaly Farghaly,Shaaban Shaaban

doi:10.3390/molecules24214009

Alsaedi Alsaedi, Farghaly Farghaly + Show 1 more

Open Access

https://doi.org/10.3390/molecules24214009

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Abstract

A novel series of pyrazolo[1,5-a]pyrimidine ring systems containing phenylsulfonyl moiety have been synthesized via the reaction of 2-(phenylsulfonyl)-1-(4-(phenylsulfonyl) phenyl)ethan-1-one, 2-benzenesulfonyl-1-(4-benzenesulfonyl-phenyl)-3-dimethylamino-propenone and 3-(dimethylamino)-1-(4-(phenylsulfonyl)phenyl)prop-2-en-1-one each with various substituted aminoazopyrazole derivatives in one pot reaction strategy. The proposed structure as well as the mechanism of their reactions were discussed and proved with all possible spectral data. The results of antimicrobial activities of the new sulfone derivatives revealed that several derivatives showed activity exceeding the activity of reference drug. Contrary to expectations, we found that derivatives containing one sulfone group are more effective against all bacteria and fungi used than those contain two sulfone groups.

Highlights

Pyrazolo[1,5-a]pyrimidine is known to be purine analog that has protruded a vital building block for pharmaceutical drugs
Three consecutive steps were enough to access of the hitherto unreported 33-(dimethylamino)-2-(phenylsulfonyl)-1-(4-(phenylsulfonyl)phenyl)prop-2-en-1-one 6 as a versatile-2-(phenylsulfonyl)-1-(4-(phenylsulfonyl)phenyl)prop-2-en-1-one 6 as a versatile multifunctional building block for construction of the targeted pyrazolo[1,5-a]pyrimidine derivatives
We started with modified method for α-bromination of 1-(4-(phenylsulfonyl)phenyl)ethan-1-one 1 derivatives

Summary

Introduction

Pyrazolo[1,5-a]pyrimidine is known to be purine analog that has protruded a vital building block for pharmaceutical drugs. Another important scaffold is benzene-sulfone moiety which present in several important pharmaceutical and agrochemical molecules due to their distinctive structural and electronic features. Due to the specific physical and chemical properties as well as the biological activities of azobenzene dyes, they have found wide

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Discussion

Conclusion