163590-19-0

Basic information

• Product Name: 3,5-diamino-4-(4-methoxybenzyl)-1H-pyrazole
• Synonyms: 3,5-diamino-4-(4-methoxybenzyl)-1H-pyrazole
• CAS NO: 163590-19-0
• Molecular Weight: 218.258
• Mol File: 163590-19-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3,5-diamino-4-(4-methoxybenzyl)-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-diamino-4-(4-methoxybenzyl)-1H-pyrazole(163590-19-0)
• EPA Substance Registry System: 3,5-diamino-4-(4-methoxybenzyl)-1H-pyrazole(163590-19-0)

Safety Data

• Hazardous Substances Data: 163590-19-0(Hazardous Substances Data)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 2826-26-8 2-(4-methoxyphenylmethylene)malononitrile 
• 5553-92-4 2-(4-methoxybenzyl)malononitrile 

Downstream Products

• 1607831-48-0 C₁₉H₂₄N₆O₅S₂ 
• 1607831-20-8 [8-(4-methoxybenzyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazin-7-yl]thiourea 

Relevant articles and documents

Discovery of mixed type thymidine phosphorylase inhibitors endowed with antiangiogenic properties: Synthesis, pharmacological evaluation and molecular docking study of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones. Part II

In our drug discovery program, a series of 2-thioxo-pyrazolo[1,5-a][1,3,5] triazin-4-ones were designed, synthesized and evaluated for their TP inhibitory potential. All the synthesized analogues conferred a varying degree of TP inhibitory activity, comparable or better than positive control, 7-deazaxanthine (7-DX, 2) (IC50 value = 42.63 μM). A systematic approach to the lead optimization identified compounds 3c and 4a as the most promising TP inhibitors, exhibiting mixed mode of enzyme inhibition. Moreover, selected compounds demonstrated the ability to attenuate the expression of the angiogenic markers (viz. MMP-9 and VEGF) in MDA-MB-231 cells at sublethal concentrations. In addition, molecular docking studies revealed the plausible binding orientation of these inhibitors towards TP, which was in accordance with the experimental results. Taken as a whole, these compounds would constitute a new direction for the design of novel TP inhibitors with promising antiangiogenic properties.

Benzylmalononitriles, a versatile synthon for the synthesis of azoles and azines as antimalarials

Diaminoisoxazoles (3a,b), 2-aminothiadiazole (5) and 3,5-diaminopyrazoles (7a-c) have been prepared from the reaction of benzylmalononitrile (1) with hydroxylamine hydrochloride, thiosemicarbazide and hydrazine hydrate separately.In one case we have been able to isolate benzylmalonamide dioxime (4a) by the reaction of 1 with hydroxylamine.Di- and tri-aminopyrimidines (2a-r) have been synthesized from the reaction of 1 with amidines and guanidine.Condensation-cyclization of 5 with ethyl acetoacetate in polyphosphoric acid provides the bis-heterocycle 6.Interaction of 7b with 4-chlorobenzyldene malononitrile affords the pyrazolopyrimidine 8.Most of the synthesized compounds have been screened for antimalarial activity against Plasmodium berghei in mice but none of them is found to show 100percent inhibition at 50 mg and 100 mg/kg dose levels.