942-32-5

Usage

Uses

Used in Pharmaceutical Industry:
3-methyl-1-phenyl-1H-pyrazol-5-ol is utilized as a building block for the synthesis of various drugs and dyes, contributing to the development of new pharmaceutical compounds with diverse therapeutic applications.
Used in Therapeutic Applications:
3-methyl-1-phenyl-1H-pyrazol-5-ol is used as an anti-inflammatory and analgesic agent, potentially offering relief from inflammation and pain due to its pharmacological properties.
Used in Antioxidant Research:
3-methyl-1-phenyl-1H-pyrazol-5-ol has been studied for its antioxidant properties, suggesting its potential use in the treatment of various diseases where oxidative stress plays a role, thereby contributing to the development of novel therapeutic strategies.
Used in Disease Treatment:
3-methyl-1-phenyl-1H-pyrazol-5-ol is being investigated for its potential use in the treatment of various diseases, highlighting its versatility and the breadth of its potential medical applications.

InChI:InChI=1/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-7,13H,1H3

Upstream product

• 59-88-1 phenylhydrazine hydrochloride 
• 89-25-8 edaravone 
• 143699-06-3 4,4'-(4-chlorophenylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ol) 
• 96068-42-7 4,4'-[(4-nitrophenyl)methylene]bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) 
• 57303-46-5 4,4'-(phenylmethylene)bis(3-methyl-1-phenyl-pyrazol-5-ol) 
• 87100-61-6 1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)butane-1,3-dione 
• 95-54-5 1,2-diamino-benzene 
• 16867-03-1 2-amino-3-hydroxypyridine 
• 2243-55-2 1-(1-naphthyl)hydrazine 
• 141-97-9 ethyl acetoacetate 
• 100-63-0 phenylhydrazine 
• 105-45-3 acetoacetic acid methyl ester 
• 99068-19-6 C₁₀H₁₂N₂O₂ 
• 6078-46-2 ethyl 3-(2-phenylhydrazono)butanoate 

Downstream Products

• 144284-93-5 C₂₇H₂₄N₄O₂*C₄H₉N 
• 23901-60-2 4-benzylidene-3-methyl-1-phenylpyrazolone 
• 25111-95-9 4,4'-benzylidene-bis(1-phenyl-3-methyl-2-pyrazolin-5-one) 
• 39143-08-3 Z-1-phenyl-3-methyl-4-<(4-dimethylaminophenyl)methylene>-5-pyrazolone 
• 132603-49-7 E-1-phenyl-3-methyl-4-<(4-dimethylaminophenyl)methylene>-5-pyrazolone 
• 39143-07-2 4-anisylidene-3-methyl-1-phenylpyrazol-5-one 
• 88689-02-5 5,5'-dimethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(4-methoxy-phenylmethanediyl)-bis-pyrazol-3-one 
• 68901-70-2 3-methyl-4-(4-nitrobenzylidene)-1-phenyl-1H-pyrazol-5(4H)-one 
• 96068-41-6 4,4'-p-nitrobenzylidene-bis(1-phenyl-3-methyl-2-pyrazolin-5-one) 
• 10389-64-7 5-methyl-4-(2-nitro-benzylidene)-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 102303-79-7 bis<4'-(3'-methyl-1'-phenylpyrazolin-5-one)yl>-2-nitrophenyl-methane 
• 210099-61-9 5-methyl-2-phenyl-4-<(E)-3-phenyl-2-propenoyl>-1,2-dihydro-3H-pyrazol-3-one 

Relevant academic research and scientific papers

4-Substituted quinoline derivatives and preparation methods and applications thereof

The present invention provides a 4-substituted quinoline derivative and preparation method and application thereof, in particular, the present invention relates to a compound shown in formula (I), a method for preparing a compound shown in formula (I), an

Pyrazole and Triazole Derivatives as Mycobacterium tuberculosis UDP-Galactopyranose Inhibitors

UDP-galactopyranose mutase (UGM) is an essential enzyme involved in the bacterial cell wall synthesis, and is not present in mammalian cells. Thus, UGM from Mycobacterium tuberculosis (Mtb) represents a novel and attractive drug target for developing antituberculosis agents. A pyrazole-based compound, MS208, was previously identified as a mixed inhibitor of MtbUGM which targets an allosteric site. To understand more about the structure activity relationship around the MS208 scaffold as a MtbUGM inhibitor, thirteen pyrazoles and triazole analogues were synthesized and tested against both MtbUGM and Mycobacterium tuberculosis in vitro. While the introduced structural modifications to MS208 did not improve the antituberculosis activity, most of the compounds showed MtbUGM inhibitory activity. Interestingly, the pyrazole derivative DA10 showed a competitive model for MtbUGM inhibition with improved Ki value of 51 ± 4 μM. However, the same compound did not inhibit the growth of Mycobacterium tuberculosis.

Design, synthesis and evaluation of dihydrotriazine derivatives-bearing 5-aryloxypyrazole moieties as antibacterial agents

Abstract: In the present investigation, a series of dihydrotriazine derivatives-bearing 5-aryloxypyrazole moieties were synthesized and their structures were confirmed by different spectral tools. The biological evaluation in vitro revealed that some of the target compounds exerted good antibacterial and antifungal activity in comparison with the reference drugs. Among these novel hybrids, compound 10d showed the most potent activity with minimum inhibitory concentration values (MIC) of 0.5?μg/mL against S. aureus 4220, MRSA 3506 and E. coli 1924 strain. The cytotoxic activity of the compounds 6d, 6m, 10d and 10g was assessed in MCF-7 and HeLa cells. Growth kinetics study showed significant inhibition of bacterial growth when treated with different conc. of 10d. In vitro enzyme study implied that compound 10d exerted its antibacterial activity through DHFR inhibition. Moreover, significant inhibition of biofilm formation was observed in bacterial cells treated with MIC conc. of 10d as visualized by SEM micrographs. Graphic abstract: Twenty-nine target compounds were designed, synthesized and evaluated in terms of their antibacterial and antifungal activities.[Figure not available: see fulltext.].

New hydrazone derivatives of pyrazole-4-carboxaldehydes exhibited anti-inflammatory properties

Background: Several series of hydrazone derivatives of pyrazole-4-carboxaldehydes (4-11) were designed and synthesized to screen their inflammatory activity. Methods: The products were characterized by1H NMR,13C NMR and HRMS. In vitro LPS-induced TNF-α model and in vivo xylene-induced ear-edema model were used to evaluate their anti-inflammatory activity. Results and Conclusion: Bioassays indicated that most of the compounds markedly inhibited the expression of TNF-α at the concentration of 10 μg/mL. Compounds 7b and 11c, two of the most potent compounds, exhibited TNF-α inhibitory ability in a dose-dependent manner with IC50 values of 5.56 and 3.69 μM, respectively. In vivo, intraperitoneal administration with 7b and 11c markedly inhibited the ear edema at the doses of 20 and 50 mg/kg. Compound 11c, inhibited edema by 49.59 % at the dose of 20 mg/kg, was comparable to the reference drug dexamethasone at the same dose (with an inhibition of 50.49 %). To understand the binding pattern, molecular docking of representa-tive 7b and 11c was performed, which demonstrated that both compounds have a forceful binding with the TNF-α, and that the phenyl and hydrazide moieties of them play a significant role in binding with the target site.

“On-water” one-pot four-component synthesis of novel 1H-furo[2,3-c]pyrazole-4-amine derivatives

A catalyst-free, simple and green protocol has been accomplished for the synthesis of novel 1H-furo[2,3-c]pyrazole-4-amines in a one-pot four-component domino reaction involving hydrazines, ethyl acetoacetate, aromatic amines and phenylglyoxal monohydrate in water. The protocol presented herein describes in situ generated pyrazolone as intermediate reactants with phenylglyoxal monohydrate in a Knoevenagel condensation followed by a Michael addition of amine, intramolecular cyclization, dehydration and the resulting to the title compound. It was observed that in this protocol bis(pyrazole-5-ols) are formed with amines bearing strong electron withdrawing groups under similar reaction conditions instead of the expected products. The reaction merits the use of water as solvent, no additive catalyst, easy workup, easy purification of products by non-chromatography and provides high yield of products with good purity.

Guanidine hydrochloride catalyzed efficient one-pot pseudo five-component synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) in water

The present methodology describes an efficient, environmentally friendly and simple protocol for the synthesis of some 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives through a one-pot pseudo-five-component reaction of hydrazine hydrate/phenyl hydrazine, ethyl acetoacetate, and various aromatic aldehydes catalyzed by guanidine hydrochloride. This condensation reaction was performed by tandem Knoevenagel–Michael reaction in water under refluxing conditions giving the title compounds in 82–92% yields. Atom economy, simple operation, easy work-up, using inexpensive organocatalyst, high yields in short times, clean transformation, and environmentally benign are some of the important features of this new protocol.

Synthesis of Pyrazolofuropyrazine via One-Pot S N Ar Reaction and Intramolecular Direct C-H Arylation

Fused-ring systems containing heterocycles are attractive templates for drug discovery. Biologically active 6-5-5+6 fused-ring systems that possess heterocycles are available, but these require a relatively large number of synthetic steps for preparation. Therefore, pyrazolofuropyrazine was designed as a 6-5-5+6 ring system template that incorporates ready accessibility for drug discovery. Pyrazolofuropyrazines were successfully constructed in only a few steps via one-pot S N Ar reaction/intramolecular C-H direct arylation. As a drug candidate, pyrazolofuropyrazine has earned a favorable LogP, although significant biological activity has yet to be established; the ready accessibility of pyrazolofuropyrazine template, however, offers an opportunity for the rapid development of promising new drug candidates.

Structure-activity relationships in a new class of non-substrate-like covalent inhibitors of the bacterial glycosyltransferase LgtC

Lipooligosaccharide (LOS) structures in the outer core of Gram-negative mucosal pathogens such as Neisseria meningitidis and Haemophilus influenzae contain characteristic glycoepitopes that contribute significantly to bacterial virulence. An important example is the digalactoside epitope generated by the retaining α-1,4-galactosyltransferase LgtC. These digalactosides camouflage the pathogen from the host immune system and increase its serum resistance. Small molecular inhibitors of LgtC are therefore sought after as chemical tools to study bacterial virulence, and as potential candidates for anti-virulence drug discovery. We have recently discovered a new class of non-substrate-like inhibitors of LgtC. The new inhibitors act via a covalent mode of action, targeting a non-catalytic cysteine residue in the LgtC active site. Here, we describe, for the first time, structure-activity relationships for this new class of glycosyltransferase inhibitors. We have carried out a detailed analysis of the inhibition kinetics to establish the relative contribution of the non-covalent binding and the covalent inactivation steps for overall inhibitory activity. Selected inhibitors were also evaluated against a serum-resistant strain of Haemophilus influenzae, but did not enhance the killing effect of human serum.

Three-component reaction for an efficient synthesis of 5-hydroxy-1-phenyl-1H-pyrazoles containing a stable phosphorus ylide moiety

A concise synthesis of new polysubstituted pyrazoles containing a phosphorane is achieved from readily available organic compounds. This C–H bond functionalization is an efficient means of selectively substituting 4-position of pyrazole to produce a five-membered aromatic ring with a chain containing ylide moiety. This protocol requires no additional catalyst and can be used for other pyrazoles including different substituents.

Design, Synthesis, DFT study and antifungal activity of pyrazolecarboxamide derivatives

A series of novel pyrazole amide derivatives were designed and synthesized by multi-step reactions from phenylhydrazine and ethyl 3-oxobutanoate as starting materials, and their structures were characterized by NMR, MS and elemental analysis. The antifungal activity of the title compounds was determined. The results indicated that some of title compounds exhibited moderate antifungal activity. Furthermore, DFT calculations were used to study the structure-activity relationships (SAR).