330158-65-1

Basic information

• Product Name: 6-amino-4-(4-methoxyphenyl)-3-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• Synonyms: 6-amino-4-(4-methoxyphenyl)-3-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• CAS NO: 330158-65-1
• Molecular Formula: C₂₀H₁₆N₄O₂
• Molecular Weight: 344.36664
• Mol File: 330158-65-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-amino-4-(4-methoxyphenyl)-3-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 6-amino-4-(4-methoxyphenyl)-3-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile(330158-65-1)
• EPA Substance Registry System: 6-amino-4-(4-methoxyphenyl)-3-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile(330158-65-1)

Safety Data

• Hazardous Substances Data: 330158-65-1(Hazardous Substances Data)

Upstream product

• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 123-11-5 4-methoxy-benzaldehyde 
• 109-77-3 malononitrile 

Relevant articles and documents

Synthesis of thiazole, thiophene, pyran and pyridine derivatives derived from 3-phenyl-1h-pyrazol-5(4h)-one with anti-proliferative, tyrosine kinase and pim-1 kinase inhibitions

Background: A wide range of pyrazole derivatives gained special attention due to their wide range of pharmacological activities especially the therapeutic activities. Many pharmacological drugs containing the pyrazole nucleus are known in the market. Method: The 3-phenyl-1H-pyrazol-5(4H)-one was the key starting compound for many heterocyclic reactions to produce substituted and fused pyrazole derivatives. Results: Antiproliferative activities of the produced compounds against six cancer cell lines A549, HT-29, MKN-45, U87MG, and SMMC-7721 and H460 were measured through which compounds showed high inhibitions. The most promising compounds were tested against tyrosine kinases (c-Kit, Flt-3, VEGFR-2, EGFR, and PDGFR). Structure-Activity Relationship (SAR) was rationalized by looking at the varying structural features of the molecules. In addition, the most active compounds were selected for Pim-1 inhibition. Conclusion: Thirty-nine pyrazole derivatives were synthesized. Nine of them 8b, 9, 12b, 12d, 14b, 15b, 18d, 18f, 19b, and 21d were the most active compounds toward the selected cancer cell lines. Compounds 12b, 14b, 18d, 18f, and 21d showed high inhibitions toward the tyrosine kinases, whereas compounds 14b, 18d, and 18f were the most potent inhibitors of Pim-1.

An efficient and green synthesis of 6-amino-3-phenyl-4-aryl-1,4- dihydropyrano [2,3-c]pyrazole-5-carbonitrile derivatives under ultrasound irradiation in aqueous medium

A facile and eco-friendly approach for the synthesis of 6-amino-3-phenyl-4-aryl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile derivatives via four-component reaction of hydrazine, ethyl 3-oxo-3- phenylpropanoate, aldehydes, and malononitrile is described. The reaction is performed in water, without using any catalyst, and under ultrasound irradiation. The developed sonochemical-assisted multi-component reaction provides an improved and accelerated conversion when compared with conventional procedure.