3347-62-4

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYL-5-PHENYL-1H-PYRAZOLE is used as a key intermediate in the synthesis of various drugs and pharmaceuticals. Its unique structure allows it to be incorporated into the molecular frameworks of different therapeutic agents, enhancing their pharmacological properties and improving their efficacy in treating various diseases.
Used in Agrochemical Industry:
3-METHYL-5-PHENYL-1H-PYRAZOLE is also used as a building block in the development of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can lead to improved performance and selectivity, making them more effective in controlling pests and unwanted plant growth.
Used in Medicinal Chemistry Research:
As a valuable tool in medicinal chemistry, 3-METHYL-5-PHENYL-1H-PYRAZOLE is used in the design and synthesis of novel compounds with potential therapeutic applications. Its unique structure and properties make it an attractive candidate for the development of new drugs and drug candidates, contributing to the advancement of drug discovery and the treatment of various diseases.
Used in Organic Synthesis:
3-METHYL-5-PHENYL-1H-PYRAZOLE is utilized as a versatile building block in organic synthesis, allowing for the creation of a wide range of organic compounds with diverse applications. Its reactivity and functional group compatibility make it a useful component in the synthesis of various organic molecules, including those with potential applications in materials science, chemical biology, and other fields.

InChI:InChI=1/C10H10N2/c1-8-7-10(12-11-8)9-5-3-2-4-6-9/h2-7H,1H3,(H,11,12)

Upstream product

• 110-91-8 morpholine 
• 79815-53-5 anhydro-2,5-diphenyl-1-hydroxy-7-methyl-3-oxopyrazolo<1,2-a>pyrazolium hydroxide 
• 77202-05-2 1-amino-5-methyl-3-phenylpyrazole 
• 90861-40-8 acetone 3-imino-1-methyl-phenylprop-1-enylhydrazone 
• 93-91-4 1-phenylbutan-1,3-dione 
• 10222-79-4 3-phenyl-5-methylpyrazole-1-carboxamide 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 126-98-7 methacrylonitrile 
• 98-86-2 acetophenone 
• 100-47-0 benzonitrile 
• 106-38-7 para-bromotoluene 
• 90888-57-6 C₁₀H₁₂N₂ 
• 100-52-7 benzaldehyde 
• 122-57-6 1-Phenylbut-1-en-3-one 

Downstream Products

• 13808-66-7 4-bromo-3-methyl-5-phenyl-1H-pyrazole 
• 92670-68-3 2-<1-(5-methyl-3-phenylpyrazolyl)>-1,4-diphenylbut-2-ene-1,4-dione 
• 77202-10-9 4-methyl-6-phenyl-1,2,3-triazine 
• 77202-05-2 1-amino-5-methyl-3-phenylpyrazole 
• 99214-42-3 1-amino-3-methyl-5-phenylpyrazole 
• 84691-22-5 4,4-Dibromo-3-methyl-5-phenyl-4H-pyrazole 
• 160730-46-1 (6aR,9R,10aR)-7-Methyl-9-(3-methyl-5-phenyl-pyrazol-1-ylmethyl)-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline 
• 115219-09-5 (6aR,9R,10aR)-7-Methyl-9-(5-methyl-3-phenyl-pyrazol-1-ylmethyl)-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline 
• 115219-09-5 (6aR,9S,10aR)-7-Methyl-9-(5-methyl-3-phenyl-pyrazol-1-ylmethyl)-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline 
• 742097-02-5 rac-2-(5-methyl-3-phenyl-pyrazol-1-yl)-1-phenylethanol 

Relevant academic research and scientific papers

Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors

Based on a new pyrazole sulfonate synthetic method, a novel class of molecules with a basic structure of pyrazole N-aryl sulfonate have been designed and synthesized. The interest in conducting intensive research stems from quite evident anti-inflammatory effects exhibited by the compounds in preliminary animal experiments. A series of compounds were synthesized by different substitutions of the R1, R2, and R3 groups. Within the series, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and phenyl 5-methyl-3-(4-(trifluoromethyl) phenyl)-1H-pyrazole-1-sulfonate exhibited excellent anti-inflammatory activity (% inhibition of auricular edemas = 27.0 and 35.9, respectively); the in vivo analgesic activity of phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate was confirmed to be effective (inhibition ratio of writhing = 50.7% and 48.5% separately), and compounds phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate were identified as selective COX-2 inhibitors (SI = 455, 10,497 and >189 severally). In Acute Oral Toxicity assays conducted in vivo, the lethal dose 50 (LD50) of 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate to mice was >2000 mg/kg BW.

Cs2CO3-promoted P-N coupling reaction of H-phosphoryl compounds with N-tosylhydrazones to afford N-phosphorylhydrazones via diazo intermediates

The Cs2CO3-promoted P-N coupling reaction of H-phosphoryl compounds and N-tosylhydrazones is reported. Formally, this transformation represents an interesting example of exchanging the sulfur and phosphorus functionalities to convert

Regiocontrolled Coupling of Alkynes and Dipolar Reagents: Iron-Mediated [3 + 2] Cycloadditions Revisited

Cyclopentadienyliron dicarbonyl based allenyliron complexes were prepared, and their formal [3 + 2] cycloaddition with a number of dipolar reagents was investigated as a means of preparing heterocyclic compounds in a regiocontrolled manner. In addition, the mechanism of the isomerization of an allenyliron complex to its propargyliron tautomer was investigated. Results in support of both radical and two-electron mechanisms for isomerization are presented.

Identification of potent anticancer copper(ii) complexes containing tripodal bis[2-ethyl-di(3,5-dialkyl-1H-pyrazol-1-yl)]amine moiety

A series of heteroleptic copper(ii) complexes of the composition [Cu(L1-5)Cl]X, where X = ClO4 and/or PF6 and [bis(2-ethyl-di(3,5-dimethyl-1H-pyrazol-1-yl))-(6-methyl-(2-pyridylmethyl))]amine (L1), [bis(2-ethyl-di(3,5-dimethyl-1H-pyrazol-1-yl))-(3,4-dimethoxy-(2-pyridylmethyl))]amine (L2), [bis(2-ethyl-di(3,5-dimethyl-1H-pyrazol-1-yl)-(2-quinolymethyl)]amine (L3), [bis(2-ethyl-di(3,5-dimethyl-1H-pyrazolyl)-(di(3,5-dimethyl-1H-pyrazol-1-yl-methyl))]amine (L4) and [bis(2-ethyl-di(3,5-dimethyl-1H-pyrazol-1-yl)-(5-methyl-3-phenyl-1H-pyrazol-1-yl-methyl)]amine (L5), were prepared and thoroughly characterized including single-crystal X-ray diffraction technique. The in vitro cytotoxicity of complexes against A2780, A2780R, HOS and MCF-7 human cancer cell lines was evaluated using the MTT test. The results revealed that complexes [Cu(L1)Cl]PF6 (1-PF6), [Cu(L2)Cl]ClO4 (2-ClO4) and [Cu(L3)Cl]PF6 (3-PF6) are the most effective, with IC50 values ranging from 1.4 to 6.3 μM, thus exceeding the cytotoxic potential of metallodrug cisplatin (IC50 values ranging from 29.9 to 82.0 μM). The complexes [Cu(L4)Cl]PF6 (4-PF6) and [Cu(L5)Cl]PF6 (5-PF6) showed only moderate cytotoxicity against A2780, with IC50 = 53.6 μM, and 33.8 μM, respectively. The cell cycle profile, time-resolved cellular uptake, interactions with small sulfur-containing biomolecules (cysteine and glutathione), intracellular ROS production, induction of apoptosis and activation of caspases 3/7 were also evaluated in the case of the selected complexes. It has been found that the best performing complexes 1 and 2 cause cell arrest in the G2/M phase and induce apoptosis via the increase in production of ROS, dominantly due to the overproduction of superoxide.

Predicting the catalytic activity of azolium-based halogen bond donors: an experimentally-verified theoretical study

This report demonstrates the successful application of electrostatic surface potential distribution analysis for evaluating the relative catalytic activity of a series of azolium-based halogen bond donors. A strong correlation (R2> 0.97) was observed between the positive electrostatic potential of the σ-hole on the halogen atom and the Gibbs free energy of activation of the model reactions (i.e., halogen abstraction and carbonyl activation). The predictive ability of the applied approach was confirmed experimentally. It was also determined that the catalytic activity of azolium-based halogen bond donors was generally governed by the structure of the azolium cycle, whereas the substituents on the heterocycle had a limited impact on the activity. Ultimately, this study highlighted four of the most promising azolium halogen bond donors, which are expected to exhibit high catalytic activity.

Heck Reactions of Acrolein or Enones and Aryl Bromides – Synthesis of 3-Aryl Propenals or Propenones and Consecutive Application in Multicomponent Pyrazole Syntheses

3-(Hetero)aryl propenals or propenones are efficiently prepared by a Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using Beller's CataCXium Ptb ligand under Jeffery's and Fu's conditions. The formation of these three-carbon building blocks is embedded into consecutive three- and pseudo-four-component syntheses of 3-(hetero)aryl and 3,5-diarylpyrazoles with a broad substitution pattern in moderate to excellent yield.

Nano-SnCl4 /SiO2 as a catalyst for one-pot synthesis of substituted 1h-pyrazoles as antifungal and cytotoxic agents

A simple and efficient method was developed for the synthesis of pyrazole derivatives via a one-pot reaction of 1,3-diketone and substituted hydrazines in the presence of nano-SnCl4/SiO2 as a mild catalyst. A series of some pyrazole derivatives (P1-P11) was synthesized and evaluated as anti-fungal and anti-cancer agents. Compounds P10 and P11 were demonstrated. The antimicrobial activities of the synthetic compounds showed that compounds P10 and P11 most excellently inhibited the growth of dermatophytes or Aspergillus species, respectively. Therefore, the cytotoxic activities of the-se compounds on two human cancer cell lines, A549 (lung cancer) and MCF-7 (breast cancer) were further assessed. Hence, results demonstrated that beside antifungal activity, P10 had also desirable cy-totoxic effect on investigated cancerous cell lines, even higher than cisplatin.

An Efficient Synthesis of Substituted Pyrazoles from One-Pot Reaction of Ketones, Aldehydes, and Hydrazine Monohydrochloride

An efficient, one-pot and metal-free process for the preparation of 3,5-disubstituted and 3,4,5-trisubstituted pyrazoles on multi-gram scale was developed. One-pot condensation of ketones, aldehydes and hydrazine monohydrochloride readily formed pyrazoline intermediates under mild conditions. Oxidation of pyrazolines, in situ, employing bromine afforded a wide variety of pyrazoles. The methodology offers a fast, and often chromatography-free protocol for the synthesis of 3,4,5-substituted pyrazoles in good to excellent yields. Alternatively, a more benign oxidation protocol affords 3,5-disubstituted or 3,4,5-trisubstituted pyrazoles by simply heating pyrazolines in DMSO under oxygen.

Sunlight-promoted Direct Irradiation of N-centred Anion: The Photocatalyst-free Synthesis of Pyrazoles in Water

A practical method through sunlight mediated annulation of α,β-unsaturated hydrazones has been developed for the synthesis of pyrazole. Based on the analysis of UV-Vis absorption of the substrate, the reaction was designed to avoid the use of external photocatalysis and proceeds via direct irradiation of N-centred anion by sunlight. The key features of this reaction include operational simplicity, readily available reagents, and amenability to gram-scale synthesis. (Figure presented.).

Discovery of DS79182026: A potent orally active hepcidin production inhibitor

Hepcidin has emerged as the central regulatory molecule of systemic iron homeostasis. Inhibition of hepcidin could be a strategy favorable to treating anemia of chronic disease (ACD). We report herein the synthesis and structure-activity relationships (SARs) of a series of benzisoxazole compounds as orally active hepcidin production inhibitors. The optimization study of multi kinase inhibitor 1 led to a potent and bioavailable hepcidin production inhibitor 38 (DS79182026), which showed serum hepcidin lowering effects in a mouse IL-6 induced acute inflammatory model.