Pyrazolo[n,m-d]Pyrimidine

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Introduction

With the continuous development of organic chemistry, cyclic compounds can provide more reaction sites and active sites. The current research on cyclic compounds mainly focuses on the research on nitrogen-containing cyclic compounds. Heterocyclic pesticides have the advantages of flexible structure, high activity and low toxicity, which are suitable for the future development of pesticides and drugs. And the research of heterocyclic compounds tends to the complex structure of heterocyclic, bi-heterocyclic and multi-heterocyclic compounds. Pyrazolopyrimidine derivatives have a wide range of biological activities because their structures are very similar to purines ^[1]. As herbicides on pesticides, pyrazolopyrimidine derivatives has the characteristics of high efficiency, low toxicity, broad spectrum, long application period, and safety to subsequent crops, so it has become a research hotspot in pesticide chemistry and medicine. The reports on pyrazolo pyrimidine compounds are mainly divided into pyrazolo pyrimidines and pyrazolo pyrimidinones.

Pyrazolo Pyrimidine and Derivatives

Chlorazophos (compound 1) is a pyrazolo[1,5-a] pyrimidine insecticide developed by Bayer in 1973 ^[2]. The earliest commercialized pyrazolo[1,5-a] pyrimidine was pyrazophos (compound 2), the earliest pyrazole fungicide, developed by Hearst in 1984. It was found that compound 3 ^[3] could affect the release of histidine. When R₁=H, R₂=OMe, the release of histidine can be inhibited; and when R₁=t-Bu, R₂=OMe, the release of histidine can be induced. 5-aminopyrazole-4-carboxylate was blocked with amino carbamic acid to obtain pyrazolopyrimidine, which was then reacted with POCl3 and primary amine to obtain compound 4 ^[4]. Compound 4 can effectively inhibit CDK-1/cyclin B and inhibit the growth of cancer cells.

Figure 1. Pyrazolo pyrimidine and its derivatives.

Pyrazolo Pyrimidinone and Derivatives

Bel ^[5] obtained compound 5 by aminoacylation followed by ring condensation. Studies have found that compounds with pyrazolo pyrimidinone structure have excellent biological activity and can selectively inhibit cGMP-PDE. Compound 5 can be used to treat diseases such as heart failure, arteriosclerosis and hypertension. Bacon synthesized pyrazolo pyrimidinones by the reaction of 5-aminopyrazoleamides with aldehydes or acid chlorides, namely compound 6 ^[6]. Compound 6 is an inhibitor of PDE and can be used to treat cardiovascular diseases. Bhuyan ^[7] synthesized 3-aminopyrazolo[3,4-d] pyrimidinone by reacting 6-hydrazino-2,4-pyrimidinedione with isocyanate in a "one-pot" method (compound 7). Compound 7 is an effective inhibitor of xanthine oxidase, which can be used clinically to control gout-related diseases and metabolic disorders.

Figure 2. Pyrazolo pyrimidinone derivatives.

The diversity of substitution sites and substituents on the pyrazolopyrimidine ring makes its structure increasingly rich. Therefore, the molecular design, synthesis and biological activity research and development of pyrazolopyrimidine compounds have great potential, and will surely become one of the hot spots in the creation of green chemicals.

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References

Bendich. et al. The synthesis and properties of 6-chloropurine and purine. Chem. Soc. 1954, 76: 6073-6077.
Hoffmann, H. et al. O-pyrazolo-pyrimidine(thiono)-phosphoric(phosphonic) acid esters and ester-amides and their use as insecticides acaricides and nematicides. National Center for Biotechnology Information. Aug, 30, 2022.
Quintela, J. et al.Pyrazolopyrimidines: synthesis, effect on histamine release from rat peritonea; mast cells and cytotoxic activity. Eur. J. Med. Chem. 2001, 36: 321-332.
Morave, J. et al. 2,6,8,9-tetrasubstituted purines as new CDK1 inhibitors. Bioorg Med Chem Lett. 2003, 13(18): 2993-6.
Bell, AS. et al. Pyrazolopyrimidones comme agents antiangineux: EP, EP0526004 A1. 1993.
Dumaitre, B.A. et al. EP0636626 (1994). Chem. Abstr. 1995.
Bhuyan, P.J. et al. Studies on uracils: a facile one-pot synthesis of pyrazolo [3,4-d] pyrimidines. Journal of Heterocyclic Chemistry. Tetrahedron Letters. 2002, 43 (5): 895-897.

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