13097-01-3

Usage

Uses

Used in Pharmaceutical Research and Development:
3-PHENYL-1H-INDAZOLE is used as a chemical building block for the synthesis of new drugs, leveraging its potential bioactivity to contribute to the creation of innovative pharmaceutical compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 3-PHENYL-1H-INDAZOLE serves as a key intermediate, facilitating the construction of complex organic molecules for a range of applications.
Used in Dye and Pigment Production:
3-PHENYL-1H-INDAZOLE is utilized as a component in the production of dyes and pigments, capitalizing on its chemical properties to enhance color characteristics and performance in various industries.
These applications highlight the multifaceted role of 3-PHENYL-1H-INDAZOLE in different sectors, underscoring its importance as a versatile chemical compound with broad potential uses.

InChI:InChI=1/C13H10N2/c1-2-6-10(7-3-1)13-11-8-4-5-9-12(11)14-15-13/h1-9H,(H,14,15)

Upstream product

• 395099-05-5 3-phenyl-1H-indazol-5-amine 
• 13047-06-8 o-bromobenzophenone 
• 857947-49-0 (2-nitro-benzenesulfonyl)-phenylacetyl-amine 
• 5350-57-2 benzophenone hydrazone 
• 96546-42-8 4-hydroxy-4,5,6,7-tetrahydro-3-phenylindazole 
• 83132-69-8 2-[(2-Benzoyl-phenyl)-hydrazono]-2-cyano-acetamide 
• 83132-64-3 Ethyl 2-benzoylphenylhydrazonocyanacetylcarbamate 
• 139215-22-8 1,1-dimethyl-8-phenyl-8H-<1,2>diazeto<1,2-a>indazol-2(1H)-one 
• 144729-20-4 3-(2-Benzoylphenyl)sydnone 
• 144729-18-0 3-<(Hydroxyimino)(phenyl)methyl>sydnone 
• 107-13-1 acrylonitrile 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 344754-25-2 Dimethyl-(3-phenyl-indazol-1-yl)-amine 
• 89568-76-3 Ethyl-methyl-(3-phenyl-indazol-1-yl)-amine 

Downstream Products

• 55076-15-8 1-(3-phenyl-1H-indazol-1-yl)ethan-1-one 
• 89215-26-9 2-methyl-3-phenyl-2H-indazole 
• 51093-42-6 1‐methyl‐3‐phenyl‐1H‐indazole 
• 61308-29-0 1-ethoxycarbonylmethyl-3-phenyl-1H-indazole 
• 61308-33-6 1-(methylcarbamoyl)methyl-3-phenyl-1H-indazole 
• 33334-13-3 2-amino-3-phenylindazole 
• 33334-10-0 1-amino-3-phenylindazole 
• 1204771-06-1 2-{(3-phenyl-1H-indazol-1-yl)methyl}thiazole-4-carboxylic acid 
• 1204771-00-5 Ethyl 2-(3-phenyl-1H-indazol-1-yl)thiazole-4-carboxylate 
• 1428979-29-6 1-(4-methoxyphenyl)-3-phenyl-1H-indazole 
• 1428979-34-3 4-(3-phenyl-1H-indazole-1-yl)benzonitrile 

Relevant academic research and scientific papers

Polymorphism vs. desmotropy: The cases of 3-phenyl- and 5-phenyl-1H-pyrazoles and 3-phenyl-1H-indazole

Two desmotropes, 3-phenyl-1H-pyrazole (1a) and 5-phenyl-1H-pyrazole (1b) have been isolated and the conditions for their interconversion established. The X-ray structure of 1b has been determined (a = 10.862(1), b = 5.7620(5), c = 12.927(2) A, β = 111.435

Switchable Synthesis of 3-Substituted 1H-Indazoles and 3,3-Disubstituted 3H-Indazole-3-phosphonates Tuned by Phosphoryl Groups

3-Alkyl/aryl-1H-indazoles and 3-alkyl/aryl-3H-indazole-3-phosphonates were synthesized efficiently through a 1,3-dipolar cycloaddition reaction between α-substituted α-diazomethylphosphonates and arynes under simple reaction conditions. The product distribution was controlled by the phosphoryl group, which acted both as a tuning group and a traceless group in the reaction.

A novel and efficient synthesis of 3-aryl and 3-heteroaryl substituted-1H-indazoles and their Mannich derivatives

A general and highly convenient procedure for the synthesis of 3-heteroaryl and 3-aryl substituted-1H-indazoles has been developed. These compounds (3a-f) were synthesized in good yield by refluxing the NaHSO3 adduct of heteroaromatic and aromatic aldehyde and phenyl hydrazine in DMF. This procedure is more general and shorter than earlier methods. Five new 3-hetero-aryl substituted-1H-indazoles were synthesized and characterized. New Mannich derivatives of 3-(1H-pyrrol-2-yl)-1H-indazole (3a) and 3-(1H-indol-3-yl)-1H-indazole (3b) were prepared from morpholine and formaldehyde.

Ni and Cu-catalyzed one pot synthesis of unsymmetrical 1,3-di(hetero)aryl-1: H -indazoles from hydrazine, o -chloro (hetero)benzophenones, and (hetero)aryl bromides

The nickel-catalyzed cyclization of in situ generated ortho-chlorobenzophenone hydrazone derivatives, to afford 3-(hetero)aryl-1H-indazoles, is documented for the first time. The product 1H-indazoles can be transformed subsequently in a one-pot procedure into 1,3-di(hetero)aryl-1H-indazoles via copper-catalyzed N-arylation with (hetero)aryl bromides.

Synthesis of highly branched oligoethylenes by air-stable N,N-indazole derivate methallyl Ni(II) complexes

Two new neutral N,N-indazole ligands bearing the carbonitrile functional group (L1 and L2) and two new air-stable cationic nickel methallyl complexes (C1 and C2) were prepared. These compounds were fully characterized by NMR, FT-IR and elemental analysis.

Unorthodox cascade reaction of arynes and: N -nitrosamides leading to indazole scaffolds

An unusual cascade annulation of arynes with N-alkyl-N-nitrosamides is developed by leveraging aryne σ-insertion and C(sp3)-H bond functionalization strategies under transition-metal-free conditions at ambient temperature, offering functionalized indazoles in high yields and regioselectivity. The protocol is scalable and exhibits a broad substrate scope. The reaction mechanism is also studied with DFT calculations.

Design, synthesis and anticandidal evaluation of indazole and pyrazole derivatives

Candidiasis, caused by yeasts of the genus Candida, is the second cause of superficial and mucosal infections and the fourth cause of bloodstream infections. Although some antifungal drugs to treat candidiasis are available, resistant strains to current therapies are emerging. Therefore, the search for new candicidal compounds is certainly a priority. In this regard, a series of indazole and pyrazole derivatives were designed in this work, employing bioisosteric replacement, homologa-tion, and molecular simplification as new anticandidal agents. Compounds were synthesized and evaluated against C. albicans, C. glabrata, and C. tropicalis strains. The series of 3-phenyl-1H-indazole moiety (10a–i) demonstrated to have the best broad anticandidal activity. Particularly, compound 10g, with N,N-diethylcarboxamide substituent, was the most active against C. albicans and both miconazole susceptible and resistant C. glabrata species. Therefore, the 3-phenyl-1H-indazole scaf-fold represents an opportunity for the development of new anticandidal agents with a new chemo-type.

Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution

The indazole scaffold represents a promising pharmacophore, commonly incorporated in a variety of therapeutic drugs. Although indazole-containing drugs are frequently marketed as the corresponding N-alkyl 1H- or 2H-indazole derivative, the efficient synthesis and isolation of the desired N-1 or N-2 alkylindazole regioisomer can often be challenging and adversely affect product yield. Thus, as part of a broader study focusing on the synthesis of bioactive indazole derivatives, we aimed to develop a regioselective protocol for the synthesis of N-1 alkylindazoles. Initial screening of various conditions revealed that the combination of sodium hydride (NaH) in tetrahydrofuran (THF) (in the presence of an alkyl bromide), represented a promising system for N-1 selective indazole alkylation. For example, among fourteen C-3 substituted indazoles examined, we observed > 99% N-1 regioselectivity for 3-carboxymethyl, 3-tert-butyl, 3-COMe, and 3-carboxamide indazoles. Further extension of this optimized (NaH in THF) protocol to various C-3, -4, -5, -6, and -7 substituted indazoles has highlighted the impact of steric and electronic effects on N-1/N-2 regioisomeric distribution. For example, employing C-7 NO2 or CO2Me substituted indazoles conferred excellent N-2 regioselectivity (≥ 96%). Importantly, we show that this optimized N-alkylation procedure tolerates a wide structural variety of alkylating reagents, including primary alkyl halide and secondary alkyl tosylate electrophiles, while maintaining a high degree of N-1 regioselectivity.

Synthesis, characterization and biological evaluation of benzimidazole and benzindazole derivatives as anti-hypertensive agents

A substituted benzimidazole and benzindazole derivatives had been synthesized having antihypertensive activity through antagonizing the angiotensin II (Ang II) receptors. The in vivo antihypertensive activity of the compounds was done with acute renal hypertension model. Two compounds TG 1 and TG 3 were found to have antihypertensive activity comparable to Telmisartan which is a prototype for Angiotensin II receptor antagonists class of drugs.In an antihypertensive study the compounds TG 1, TG 2 and TG 3 had systolic blood pressures of 147.2 mm/Hg, 168.2 mm/Hg, and 126.3 mm/Hg, respectively. This systolic blood pressure was lower than the disease control vehicle-treated rodents, which had a systolic blood pressure of 167.2 mm/Hg. The diastolic blood pressure was 119.7 mm/Hg, 124.7 mm/Hg and 88.83 mm/Hg, respectively and that of the disease control vehicle-treated rodents was 122.3 mm/Hg. TG 3 had comparable decrease in the MABP to Telmisartan. These encouraging results make compound TG 3 effective anti-hypertensive drug candidate and worthy of further investigation.

Copper-Promoted Oxidative Intramolecular C–H Amination of Hydrazones to Synthesize 1H-Indazoles and 1H-Pyrazoles Using a Cleavable Directing Group

A facile and efficient synthesis of 1H-indazoles and 1H-pyrazoles through a copper-promoted oxidative intramolecular C–H amination of hydrazones using a cleavable directing group was developed. This reaction is characterized by its mild conditions, operational simplicity, readily available reagents, and excellent yields. A tentative mechanism for Cu-mediated C–H oxidative amination was proposed.