5346-56-5

Usage

Uses

Used in Pharmaceutical Industry:
5-Amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile is used as a building block for the development of new drugs due to its potential biological activities, such as anti-inflammatory, antioxidant, and analgesic properties. Its presence in various medical drugs highlights its importance in the pharmaceutical industry.
Used in Agricultural Industry:
5-Amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile is used as a component in the formulation of agricultural products, particularly those with antibacterial and antifungal properties. Its incorporation into these products helps in controlling plant diseases and promoting healthy crop growth.
Used in Research and Development:
5-Amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile is used as a research compound for studying its potential applications in various fields, including medicine and agriculture. Its diverse biological activities make it a valuable tool for scientists to explore new therapeutic and protective agents.

InChI:InChI=1/C11H8N4O5/c16-14(17)7-3-4-9-8(6-7)13(10-2-1-5-12-10)11(20-9)15(18)19/h1-6,11-12H

Upstream product

• 53106-29-9 5-amino-3-methyl-1-phenyl-1H-5-pyrazole carbaldehyde oxime 
• 1131-17-5 5-chloro-3-methyl-1-phenyl-1H-pyrazole 
• 947-95-5 5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole 
• 114362-54-8 5-azido-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 1187-11-7 acetylmalonodinitrile 
• 100-63-0 phenylhydrazine 
• 75-07-0 acetaldehyde 
• 109-77-3 malononitrile 
• 78-39-7 Triethyl orthoacetate 
• 5515-16-2 2-(methoxyethylidene)propanedinitrile 
• 59-88-1 phenylhydrazine hydrochloride 
• 52217-35-3 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 101309-49-3 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbothioamide 
• 5417-82-3 (1-ethoxyethylidene)malononitrile 

Downstream Products

• 1131-18-6 1-Phenyl-3-methyl-5-aminopyrazole 
• 18093-92-0 3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile 
• 173260-04-3 dimethyl 4-amino-3-methyl-1-phenylpyrazolo<3,4-b>pyridine-5,6-dicarboxylate 
• 913607-91-7 4-imino-3-methyl-1,5-diphenyl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-d]pyrimidine-6-thione 
• 194543-23-2 5-(N-methoxycarbonylamino)-4-cyano-3-methyl-1-phenyl-(1H)-pyrazole 
• 87412-87-1 3-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 205753-30-6 4-chloro-3-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 1146953-46-9 4-chloro-3,4-dimethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 

Relevant academic research and scientific papers

Crystal structure, IR spectroscopic and optical properties of the two (C11N4H10)4·H2O and (C11N4H10)2·H2O compounds

The crystallization of (C11N4H10)2·H2O (I) and (C11N4H10)4·H2O (II) is made by slow evaporation from aqueous solutions. The structures of these c

Metal-free ring opening of 5-amino-1,4-diaryl-1H-pyrazoles: A facile access to 2-aryl-3-arylazoacrylonitriles

Various 2-aryl-3-arylazoacrylonitriles are synthesized while attempting the intramolecular N-arylation of 5-aminopyrazoles, using the hypervalent iodine reagent. The synthesis involves phenyl iodine diacetate-assisted ring opening of 5-aminopyrazoles at r

Synthesis and in silico docking of new pyrazolo[4,3-e]pyrido[1,2-a]pyrimidine-based cytotoxic agents

To explore a new set of anticancer agents, a novel series of pyrazolo[4,3-e]pyrido[1,2-a]pyrimidine derivativeshave been designed and synthesized viacyclocondensation reactions of pyrazolo-enaminone with a series of arylidenemalononitriles; compound 5 was

Core-shell structured magnetite silica-supported hexatungstate: A novel and powerful nanocatalyst for the synthesis of biologically active pyrazole derivatives

This article describes the synthesis of a novel core-shell structured magnetic silica-supported hexatungstate (Fe3O4@SiO2-NH3[W6O19]) nanocatalyst through immobilization of hexatungstate on

New pyrazolo-triazolo-pyrimidine derivatives as antibacterial agents: Design and synthesis, molecular docking and DFT studies

A new series of antibacterial pyrazolo-triazolo-pyrimidine derivatives 3a-3i were synthesized in two steps starting from aminopyrazole 1 and characterized by 1H NMR 13C NMR and HRES-MS. Their molecular geometry are also calculated by the Density Functional Theory (DFT) employing B3LYP level with 6-311G (d,p) basis set. All the synthesized compounds were tested for in vitro antibacterial activity against a panel of selected bacterial strains, by application of the Disc-Diffusion and MIC assays, using gentamicin as standard. The interactions of these compounds with the bacteria Pseudomonas aeruginosa (LasR) were performed by molecular docking studies.

Synthesis of pyrazolopyrimidinones as sildenafil derivatives and sclerotigenin

A series of novel pyrazolo pyrimidinone derivatives (3(a–d), 4(a–d), and 6(a–d)) was synthesized from various pyrazolo amides (2a–d) which are synthesized by the reaction between ethyl 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxylate (1) and various lithium amides. In addition, we also described the synthesis of sclerotigenin drug molecule which has quinazoline moiety from simple 2-nitro benzoic acid with high yields.

Design and synthesis of pyrazolo[3,4-d]pyrimidines: Nitric oxide releasing compounds targeting hepatocellular carcinoma

A new series of pyrazolo[3,4-d]pyrimidines tethered with nitric oxide (NO) producing functionality was designed and synthesized. Sulforhodamine B (SRB) protein assay revealed that NO releasing moiety in the synthesized compounds significantly decreased the cell growth more than the des-NO analogues. Compounds 7C and 7G possessing N-para-substituted phenyl group, released the highest NO concentration of 4.6% and 4.7% respectively. Anti-proliferative activity of synthesized compounds on HepG2 cell line identified compounds 7h, 7p, 14a and 14b as the most cytotoxic compounds in the series of IC50?=?3, 5, 3 and 5?μM, respectively, compared to erlotinib as a reference drug (IC50?=?25?μM). Flow cytometry studies revealed that 7?h arrested the cells in G0/G1 phase of cell cycle while 7p arrested the cells in S phase. Moreover, docking study of the synthesized compounds on EGFR (PDB code: 1M17) and cytotoxicity study indicated that N-1 phenyl para substitution, pyrazole C-3 alkyl substitution and tethering the nitrate moiety through butyl group had a significant impact on the activity.

Synthesis and in vitro antibacterial evaluation of 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines

Pyrazolo[3,4-d]pyrimidines are one of the most important classes of fused heterocyclic compounds which exhibit a broad range of biological and medicinal properties. They are known as anticancer, antifungal, antibacterial, antiviral and anti-inflammatory agents. In this study, some new 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidine derivatives were prepared via reaction of 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile with various nitriles in the presence of sodium ethoxide as catalyst. The inhibitory properties of synthesized compounds were studied according to CLSI guidelines against some pathogenic bacteria including four gram-positive strains (Streptococcus pyogenes, Staphylococcus aureus, Bacillus cereus and Bacillus subtilis subsp. spizizenii) and three gram-negative strains (Pseudomonas aeruginosa, Shigella flexneri and Salmonella enterica subsp. enterica). The antibacterial effects of all derivatives were compared with those of antibiotics belonging to different classes. The values were reported as inhibition zone diameter (IZD), minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). The effect of substituents on the biological activity of derivatives was discussed as well. The inhibitory effect of compound 6a, was shown to be the most, with MIC values in the range of 32-4096 μg/mL. Since most of the synthesized compounds were effective against Streptococcus pyogenes and Pseudomonas aeruginosa, they can be considered as inhibitors of these two bacteria.

MgO nanoparticle-catalyzed, solvent-free Hantzsch synthesis and antibacterial evaluation of new substituted thiazoles

Abstract: In this study, some novel 4-thiazolylpyrazoles were synthesized by modified Hantzsch method, under solvent-free conditions and in the presence of MgO nanoparticles as catalyst. Excellent yields in shorter reaction times were achieved under the n

Evaluation and structure-activity relationship analysis of a new series of 4-imino-5H-pyrazolo[3,4-d]pyrimidin-5-amines as potential antibacterial agents

The synthesis of pyrazolo[3,4-d]pyrimidine derivatives is important due to their presence in various biologically active compounds such as anticancer, antimicrobial, antiparasitic, anti-inflammatory and antidiabetic agents. In this project, a new and efficient approach for the synthesis of some novel 4-imino-5H-pyrazolo[3,4-d]pyrimidin-5-amines from reaction of 5-amino-pyrazole-4-carbonitrile with various hydrazides in ethanolic sodium ethoxide medium was reported. Antimicrobial activities of all synthesized derivatives were evaluated against eight Gram-positive and five Gram-negative pathogenic bacteria. The moderate to good inhibitory effects were observed based on inhibition zone diameter (IZD), minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values. In order to determine the reasonable relationship between antibacterial activities and physiochemical properties of the derivatives, computational studies were carried out in terms of geometry optimization, short-range van der Waals forces, dipole moments, atomic charges and frontier orbital energies. It was found that both short-range forces and covalent bonds are important in the observed inhibitory effects of the molecules. The results suggested that pyrazolo[3,4-d]pyrimidine derivatives prefer a soft nucleophilic attack on bio-macromolecular targets. Furthermore, our models proposed that the antibacterial activities of these derivatives can be improved by substituting large electron donating groups on the 6-phenyl rings.