28561-80-0

Usage

Uses

Used in Medicinal Chemistry:
1-Phenyl-1H-indazole-3-ol is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its ability to modulate biological targets makes it a valuable component in the development of new drugs with specific therapeutic effects.
Used in Drug Development:
1-Phenyl-1H-indazole-3-ol is utilized as a lead compound in drug discovery processes. Its potential to interact with specific biological targets allows researchers to explore its efficacy in treating various diseases and conditions, thereby contributing to the advancement of novel therapeutic agents.
Used in Research and Development:
1-Phenyl-1H-indazole-3-ol serves as a key research tool in the study of indazole derivatives and their pharmacological properties. It aids scientists in understanding the structure-activity relationships of these compounds, which is crucial for optimizing their therapeutic potential and guiding the design of more effective drugs.

InChI:InChI=1/C13H10N2O/c16-13-11-8-4-5-9-12(11)15(14-13)10-6-2-1-3-7-10/h1-9H,(H,14,16)

Upstream product

• 532-96-7 N-benzoyl-N'-phenylhydrazine 
• 30086-49-8 2-amino-N'-phenylbenzohydrazide 
• 118-48-9 isatoic anhydride 
• 723-89-7 1-phenyl-indole-2,3-dione 
• 122-39-4 diphenylamine 
• 382165-80-2 N-nitrosodiphenylamine 
• 87885-95-8 2-Phenylamino-benzoic acid 1-phenyl-1H-indazol-3-yl ester 
• 17223-83-5 N_.N-diphenylcarbamoyl azide 
• 87885-91-4 C₂₆H₁₈N₄O₃ 
• 50625-52-0 2-bromo-N'-phenylbenzohydrazide 
• 79271-24-2 2-iodo-N'-phenylbenzohydrazide 
• 609-67-6 2-Iodobenzoyl chloride 
• 88-67-5 2-Iodobenzoic acid 
• 100-63-0 phenylhydrazine 

Downstream Products

• 25854-97-1 N-Nitrozo-N-phenyl-anthranilic acid 
• 85581-08-4 1-Phenyl-2-(4-bromobutyl)-2,3-dihydro-1H-indazol-3-one 

Relevant academic research and scientific papers

Synthesis of quaternary carbon-centered indolo[1,2-a]quinazolinones and indazolo[1,2-a]indazolonesviaC-H functionalization

An unprecedented Ru(ii)-catalyzed Csp2-H bond activation and annulation reaction of phenylindazolones with diaryl-substituted alkynes and dialkyl-substituted alkynes provided efficient routes for the construction of all-carbon quaternary-centered indolo[1,2-a]quinazolinones and quaternary carbon-centered indazolo[1,2-a]indazolones, respectively. The indolo[1,2-a]quinazolinones were fomedviaCsp2-H activation, alkyne insertion and a 1,2-phenyl shift. Indazolo[1,2-a]indazolones were formed through a cascade reactionviathe formation of exocyclic double bonds containing indolo[1,2-a]quinazolinones.

Method for synthesis of indazolone compound

The invention provides a novel method for synthesis of an indazolone compound. The method comprises that an alkali is added into o-halogenated aromatic formylhydrazine as a raw material, and the mixture is heated in a solvent so that a 1-aryl and 2-aryl indazolone compound having a high yield is obtained. The method is free of a transition metal catalyst, is simple in operation, has a high reaction yield and has a very high practical value in industrial preparation of the indazolone compound.

Synthesis of Indazolones via Friedel-Crafts Cyclization of Blocked (Masked) N-Isocyanates

Nitrogen-substituted isocyanates (N-isocyanates) are rare amphoteric reagents with high, but underdeveloped synthetic potential. Herein, we study the formation of indazolones by Friedel-Crafts cyclization of N-isocyanates using blocked (masked) N-isocyanate precursors: the effect of the masking group and the reaction scope have been delineated. Substrate synthesis has also been improved using a reported copper-catalyzed coupling of arylbismuth(V) reagents that is compatible with the hemilabile OPh blocking group.

A Convenient Synthesis of 1-Aryl- A nd 2-Aryl-Substituted Indazolones via Intramolecular C-N Coupling Promoted by KO t-Bu

A new method for the synthesis of 1-arylindazolones and 2-arylindazolones from N′-aryl-2-halobenzohydrazides promoted by KOt-Bu was developed. The difference of 2-halogen substituent exerted a significant effect on the distribution of the products. Two di

Synthesis of cinnolines via Rh(III)-catalysed dehydrogenative C-H/N-H functionalization: Aggregation induced emission and cell imaging

Rhodium catalysed dehydrogenative C-H/N-H functionalization was developed to construct phthalazino[2,3-a]-/indazolo[1,2-a]cinnolines by reacting N-phenyl phthalazine/indazole with alkynes. The synthesized compounds exhibit prominent fluorescence properties in solid and aggregation states. Their application in cell imaging was investigated using various cancer cell lines.

Rhodium(III)-catalyzed N-nitroso-directed C-H addition to ethyl 2-oxoacetate for cycloaddition/fragmentation synthesis of indazoles

RhIII-catalyzed N-nitroso-directed C-H addition to ethyl 2-oxoacetate allows subsequent construction of indazoles, a privileged heterocycle scaffold in synthetic chemistry, through the exploitation of reactivity between the directing group and installed group. The formal [2+2] cycloaddition/fragmentation reaction pathway identified herein, a unique reactivity pattern hitherto elusive for the N-nitroso group, emphasizes the importance of forward reactivity analysis in the development of useful C-H functionalization-based synthetic tools. The synthetic utility of the protocol is demonstrated with the synthesis of a tri-cyclic-fused ring system. The diversity of covalent linkages available for the nitroso group should enable the extension of the genre of reactivity reported herein to the synthesis of other types of heterocycles.

Copper-catalyzed synthesis of substituted indazoles from 2-chloroarenes at low catalyst-loading

An efficient and convenient access to 1-substituted indazol-3-ones 2 has been achieved throughout the intramolecular C-N bond formations of 2-chloro-benzoic acid-N′-aryl and alkyl-hydrazides employing 0.5 mol% of cuprous (I) iodide and 20 mol% of l-prolin

Assembly of N, N -disubstituted hydrazines and 1-aryl-1 H-indazoles via copper-catalyzed coupling reactions

CuI-catalyzed coupling of N-acyl-N′-substituted hydrazines with aryl iodides takes place at 60-90 °C to afford N-acyl-N′,N′- disubstituted hydrazines regioselectively and thereby gives a facile method for assembling N,N-diaryl hydrazines. N-Acyl-N′-substituted hydrazines can also react with 2-bromoarylcarbonylic compounds at 60-125 °C under the catalysis of CuI/4-hydroxy-l-proline to provide 1-aryl-1H-indazoles.

Copper-catalyzed mild and efficient entry to 1-substituted indazolones

A variety of 1-alkyl- and aryl-substituted indazolones were synthesized easily starting from commercially available 2-halobenzoic acids and hydrazines via the copper-catalyzed intramolecular C-N bond formation of 2-halobenzohydrazides under mild conditions.

Synthesis and biological evaluation of novel pyrazoles and indazoles as activators of the nitric oxide receptor, soluble guanylate cyclase

Database searching and compound screening identified 1-benzyl-3-(3-dimethylaminopropyloxy)-indazole (benzydamine, 3) as a potent activator of the nitric oxide receptor, soluble guanylate cyclase. A comprehensive structure-activity relationship study surrounding 3 clearly showed that the indazole C-3 dimethylaminopropyloxy substituent was critical for enzyme activity. However replacement of the indazole ring of 3 by appropriately substituted pyrazoles maintained enzyme activity. Compounds were evaluated for inhibition of platelet aggregation and showed a general lipophilicity requirement. Aryl-substituted pyrazoles 32, 34, and 43 demonstrated potent activation of soluble guanylate cyclase and potent inhibition of platelet aggregation. Pharmacokinetic studies in rats showed that compound 32 exhibits modest oral bioavailability (12%) Furthermore 32 has an excellent selectivity profile notably showing no significant inhibition of phosphodiesterases or nitric oxide synthases.