130925-67-6

Upstream product

• 50427-77-5 5-amino-1-phenyl-1H-pyrazole-4-carboxamide 
• 93-89-0 benzoic acid ethyl ester 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 100-52-7 benzaldehyde 
• 100-63-0 phenylhydrazine 
• 123-06-8 Ethoxymethylenemalononitrile 
• 538-51-2 benzylidene phenylamine 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 205753-32-8 4-chloro-1,6-diphenyl-1H-pyrazolo[3,4-d]pyrimidine 

Relevant academic research and scientific papers

Pharmacophore-linked pyrazolo[3,4-d]pyrimidines as EGFR-TK inhibitors: Synthesis, anticancer evaluation, pharmacokinetics, and in silico mechanistic studies

Targeting the epidermal growth factor receptors (EGFRs) with small inhibitor molecules has been validated as a potential therapeutic strategy in cancer therapy. Pyrazolo[3,4-d]pyrimidine is a versatile scaffold that has been exploited for developing potential anticancer agents. On the basis of fragment-based drug discovery, considering the essential pharmacophoric features of potent EGFR tyrosine kinase (TK) inhibitors, herein, we report the design and synthesis of new hybrid molecules of the pyrazolo[3,4-d]pyrimidine scaffold linked with diverse pharmacophoric fragments with reported anticancer potential. These fragments include hydrazone, indoline-2-one, phthalimide, thiourea, oxadiazole, pyrazole, and dihydropyrazole. The synthesized molecules were evaluated for their anticancer activity against the human breast cancer cell line, MCF-7. The obtained results revealed comparable antitumor activity with that of the reference drugs doxorubicin and toceranib. Docking studies were performed along with EGFR-TK and ADMET profiling studies. The results of the docking studies showed the ability of the designed compounds to interact with key residues of the EGFR-TK through a number of covalent and noncovalent interactions. The obtained activity of compound 25 (IC50 = 2.89 μM) suggested that it may serve as a lead for further optimization and drug development.

Novel Pyrazolo[3,4- d]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation

Plant pathogenic fungi seriously threaten agricultural production. There is an urgent need to develop novel fungicides with low toxicity and high efficiency. In this study, we designed and synthesized 44 pyrazolo[3,4-d]pyrimidin-4-one derivatives and evaluated them for their fungicidal activities. The bioassay data revealed that most of the target compounds possessed moderate to high in vitro antifungal activities. Especially compound g22 exhibited remarkable antifungal activity against Sclerotinia sclerotiorum with an EC50 value of 1.25 mg/L, close to that of commercial fungicide boscalid (EC50 = 0.96 mg/L) and fluopyram (EC50 = 1.91 mg/L). Moreover, compound g22 possessed prominent protective activity against S. sclerotiorum in vivo for 24 h (95.23%) and 48 h (93.78%), comparable to positive control boscalid (24 h (96.63%); 48 h (93.23%)). Subsequent studies indicated that compound g22 may impede the growth and reproduction of S. sclerotiorum by affecting the morphology of mycelium, destroying cell membrane integrity, and increasing cell membrane permeability. In addition, the application of compound g22 did not injure the growth or reproduction of Italian bees. This study revealed that compound g22 is expected to be developed for efficient and safe agricultural fungicides.

A synthesis of pyrazolo [3, 4 - d] pyrimidine -4 - ketone compounds (by machine translation)

The invention provides a novel synthetic method for pyrazolo[3,4-d]pyrimidine-4-ketone compounds. The method employs reaction of hydrazine and methylene malononitrile with aldehyde to synthesize target compounds. The method has a reaction general formula

Base-catalyzed one-pot tandem reaction: An effective strategy for the synthesis of pyrazolo[3,4-d]pyrimidinone derivatives

An effective one-pot multicomponent synthesis of pyrazolo[3,4-d]pyrimidinone derivatives through the tandem heterocyclization of hydrazine, methylenemalononitrile and aldehyde has been developed. This highly effective method includes nucleophilic addition

Versatile synthesis of 6-alkyl/aryl-1H-pyrazolopyrimidin-4-ones

Condensation of 5-amino-1H-pyrazole-4-carboxamide (1a) with various aromatic aldehydes furnishes 6-substituted-1H-pyrazolepyrimidin-4(5H)-ones (4a-f) via the intermediates 5-(N-arylideneamino)pyrazole-4-carboxamides (3a-f).Compounds 4a-f have also

STUDIES ON PYRAZOLOPYRIMIDINE DERIVATIVES. XVIII. FACILE PREPARATION OF 1H-PYRAZOLOPYRIMIDIN-4(5H)-ONES

Reaction of 5-amino-1-phenyl-1H-pyrazole-4-carboxamide (4) with the esters (3a-h) in the presence of sodium ethoxide in ethanol gave 1-phenyl-1H-pyrazolopyrimidin-4(5H)-one (1a) and its 6-substituted derivatives (1b-h).Similar treatment of 5-amino-1-methyl-1H-pyrazole-4-carboxamide (5) with 3a-h gave the 1-methyl-1H-pyrazolopyrimidin-4(5H)-ones (2a-h).