Abstract
5-Amino-3-(4-chlorophenylamino)-1 H -pyrazole-4-carbonitrile 3 was prepared in high yield from the reaction of hydrazine hydrate with known 2-[(4-chlorophenylamino)(methylthio)methylene]malononitrile 2a (which was prepared from reaction of 2-[bis(methylthio)methylene]malononitrile 1 with p -Chloroaniline) under reflux in ethanol. The compound 3 was utilized as a key intermediate for the synthesis of pyrazolo[1, 5- a ]pyrimidines 4a-b, 5a-c and 6 by reactions with some of ketene- S , S -and N , S -acetals. The antibacterial and antifungal activities, as well cytotoxicity against Breast cancer cells (MCF7) of some selected compounds are also reported.
Highlights
Pyrazolopyrimidine derivatives constitute an interesting class of heterocycles because of their synthetic versatility, effective biological activities, and pharmacological importance as purine analogs [1,2,3,4,5]
Various related compounds of pyrazolopyrimidines have antitumor and antileukemic activities [6, 7]. Several derivatives such as 4hydroxypyrazolopyrimidine, which are used in the treatment of hyperuricemia and gout, inhibit de novo purine biosynthesis and xanthine oxidase [8]
We report in this paper novel synthesis of functionalized pyrazolo [1, 5-a] pyrimidines 4a-b, 5a-c, 6 by the reactions of 5-aminopyrazole 3 with respective 2-[bismethylene]malononitrile 1, ethyl 2-cyano-3,3bis[methylthio]acrylate, α, α-dicyanoketene-N, S-acetals 2ac
Summary
Pyrazolopyrimidine derivatives constitute an interesting class of heterocycles because of their synthetic versatility, effective biological activities, and pharmacological importance as purine analogs [1,2,3,4,5]. Various related compounds of pyrazolopyrimidines have antitumor and antileukemic activities [6, 7]. Several derivatives such as 4hydroxypyrazolopyrimidine (allopurin), which are used in the treatment of hyperuricemia and gout, inhibit de novo purine biosynthesis and xanthine oxidase [8]. Cyclization of 5-aminopyrazoles with ketene-S,S and N,S-acetals is the most widely used route for the synthesis of pyrazolopyrimidines [9,10,11,12]. We report in this paper novel synthesis of functionalized pyrazolo [1, 5-a] pyrimidines 4a-b, 5a-c, 6 by the reactions of 5-aminopyrazole 3 with respective 2-[bis (methylthio)methylene]malononitrile 1, ethyl 2-cyano-3,3bis[methylthio]acrylate, α, α-dicyanoketene-N, S-acetals 2ac. The antibacterial, antifungal, cytotoxicity testing results of some selected compounds is included
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