55271-06-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-METHOXY-PHENYL)-1H-INDAZOLE is used as a potential drug candidate for its pharmacological properties, making it suitable for the development of therapeutic agents for a range of conditions.
Used in Pre-Clinical Research:
3-(4-METHOXY-PHENYL)-1H-INDAZOLE is used as a subject of investigation in pre-clinical research to explore its potential uses and effects, with ongoing studies aimed at understanding its pharmacological actions and applications in medicine.

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 66607-27-0 3-iodoindazole 
• 40598-94-5 3-bromo-1H-indazole 
• 19350-72-2 N'-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 1373397-21-7 2-(trimethylsilyl)phenyl imidazol-1-sulfonate 
• 1441096-60-1 3-ethoxy-1-tosyl-1H-indazole 
• 825-60-5 benzimidic acid ethyl ester 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1885-29-6 anthranilic acid nitrile 
• 54118-74-0 2-chloro-4'-methoxybenzophenone 
• 609-65-4 o-chlorobenzoyl chloride 
• 41920-22-3 Dimethyl (α-diazo-p-methoxybenzyl)phosphonate 

Downstream Products

• 1569280-69-8 C₂₀H₁₇N₃O₃S 
• 1204771-24-3 C₁₈H₁₃N₃O₃S 
• 1451489-90-9 3-(4-methoxyphenyl)-1,2-dimethyl-2,3-dihydro-1H-indazole 
• 51093-44-8 3‐(4‐methoxyphenyl)‐1‐methyl‐1H‐indazole 

Relevant academic research and scientific papers

Arylation Using Sulfonamides: Phenylacetamide Synthesis through Tandem Acylation-Smiles Rearrangement

A range of electron-poor and heterocyclic sulfonamides react with phenylacetyl chlorides to produce benzhydryl derivatives in a single step. The reaction proceeds via tandem amide bond formation/Dohmori-Smiles rearrangement under the simple conditions of

A facile route to 1: H- A nd 2 H-indazoles from readily accessible acyl hydrazides by exploiting a novel aryne-based molecular rearrangement

Herein we report the transformation of readily synthesised acyl hydrazides into 2-hydrazobenzophenones via a novel molecular rearrangement pathway using aryne chemistry. The developed reaction protocol is performed under relatively mild conditions and is

Synthesis of 3-aryl/heteroaryl-1-methyl-1H-indazoles and evaluation of their biological activities

The synthesis of 3-aryl/heteroaryl-1-methyl-1H-indazole derivatives (5a-j) was achieved from commercially available 1H-indazole through the Suzuki cross-coupling reaction. The indazoles 5a-j were synthesized through two alternative routes (Route 1 and Route 2) from the same starting material and characterized using1H nuclear magnetic resonance (NMR),13C NMR, infrared, and liquid chromatography-mass spectrometry data. The first step which is common step to both routes involves conversion of 1H-3-iodo-1H-indazole (2). The antibacterial activity of 5a-j and intermediates 3a-j was evaluated against two Gram-positive and two Gram-negative bacterial strains and anticancer activity against HT-29 and MDA-MB-231cancer cell lines.

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.

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.

A Synthesis of 1H-Indazoles via a Cu(OAc)2-Catalyzed N-N Bond Formation

A facile synthesis of 1H-indazoles featuring a Cu(OAc)2-catalyzed N-N bond formation using oxygen as the terminal oxidant is described. The reaction of readily available 2-aminobenzonitriles with various organometallic reagents led to o-aminoar

Microwave assisted solvent-free C-H amination by silica-supported manganese dioxide

An effective and convenient method has been developed for the preparation of 1-unsubstituted 1H-indazoles via C-H amination of N-acetylhydrazones in the presence of a catalytic amount of manganese dioxide under microwave irradiation. This new method featured easy operation and relatively short reaction-time.

Elemental step thermodynamics of various analogues of indazolium alkaloids to obtaining hydride in acetonitrile

A series of analogues of indazolium alkaloids were designed and synthesized. The thermodynamic driving forces of the 6 elemental steps for the analogues of indazolium alkaloids to obtain hydride in acetonitrile were determined using an isothermal titration calorimeter (ITC) and electrochemical methods, respectively. The effects of molecular structure and substituents on the thermodynamic driving forces of the 6 steps were examined. Meanwhile, the oxidation mechanism of NADH coenzyme by indazolium alkaloids was examined using the chemical mimic method. The result shows that the oxidation of NADH coenzyme by indazolium alkaloids in vivo takes place by one-step concerted hydride transfer mechanism.

A general synthesis of diversely substituted indazoles and hetero-aromatic derivatives from o-halo-(het)arylaldehydes or -phenones

A set of variously substituted indazoles and hetero-aromatic derivatives were synthesized from o-halo-(het)arylaldehydes using a palladium catalyzed amination followed by cyclization. Starting from phenones, this process was extended to give 3-substituted indazoles. Moreover, N-1-substituted-indazoles can be reached by this strategy using an optional selective N-1-alkylation step during the process. This methodology offers a general and easy route for the synthesis of regioselectively substituted indazoles.

Discovery of 2-(1H-indazol-1-yl)-thiazole derivatives as selective EP 1 receptor antagonists for treatment of overactive bladder by core structure replacement

We have designed a series of potent EP1 receptor antagonists. These antagonists are a series of 2-(1H-indazol-1-yl)-thiazoles in which the core structure was replaced with pyrazole-phenyl groups. In preliminary conscious rat cystometry experiments, two representative candidates, 2 and 22, increased bladder capacity. In particular, the increase using 22 was approximately 2-fold that of the baseline. More detailed profiling of this compound and further optimization of this series promises to provide a novel class of drug for treating overactive bladder (OAB).