89438-55-1

Usage

InChI:InChI=1/C11H14N2O/c1-2-3-8-13-11(14)9-6-4-5-7-10(9)12-13/h4-7,12H,2-3,8H2,1H3

Upstream product

• 89438-43-7 2-Butyl-3-oxo-2,3-dihydro-indazole-1-carboxylic acid ethyl ester 
• 542-69-8 1-iodo-butane 
• 7364-25-2 3-indazolinone 
• 16105-24-1 ethyl 2,3-dihydro-3-oxo-1H-indazole-1-carboxylate 
• 612-25-9 2-Nitrobenzyl alcohol 
• 109-73-9 N-butylamine 
• 64-17-5 ethanol 
• 79903-04-1 N-butyl-2-nitrobenzamide 
• 552-16-9 ortho-nitrobenzoic acid 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 1016230-13-9 C₁₁H₁₅IN₂O 

Downstream Products

• 1016230-14-0 2-butyl-2,3-dihydro-1-[[2'-[2-(triphenylmethyl)-2H-tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]-1H-indazol-3-one 

Relevant academic research and scientific papers

A B2(OH)4-Mediated Synthesis of 2-Substituted Indazolone and Its Application in a DNA-Encoded Library

Indazolone cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. In this report, a mild and efficient approach to 2-substituted indazolones via B2(OH)4-mediated reductive N-N b

Rapid and halide compatible synthesis of 2-: N -substituted indazolone derivatives via photochemical cyclization in aqueous media

Indazolone derivatives exhibit a wide range of biological and pharmaceutical properties. We report a rapid and efficient approach to provide structurally diverse 2-N-substituted indazolones via photochemical cyclization in aqueous media at room temperatur

Preparation method for synthesizing indazolinone compound by carbon dioxide promotion and photocatalyst-free photo-induction

The invention discloses a preparation method for synthesizing an indazolinone compound by carbon dioxide promotion and photocatalyst-free photo-induction. A quinoline 2-nitrobenzyl alcohol compound and an amine derivative serve as raw materials, low-priced and easily available common bulbs serve as reaction light sources, carbon dioxide serves as a promoter, common organic solvents serve as reaction solvents, reaction is performed at a certain temperature for a certain time, the indazolinone compound can be prepared in a high-yield and high-selectivity manner, and high yield is obtained in gram-scale amplification reaction.

Photocatalyst-free Synthesis of Indazolones under CO2 Atmosphere

A convenient photocatalyst-free method for the synthesis of redox-active 1,2-dihydro-3H-indazol-3-one derivatives from (2-nitroaryl)methanol and amines was developed. The reaction proceeded efficiently at room temperature by irradiation of UV light under CO2 atmosphere (1.0 atm, flow) without any photocatalysts or additives. This mild, operationally simple method shows wide functional tolerance. The carbamate formed in situ from CO2 and amine is proposed to be the key of this reaction. Some of these compounds synthesized by the present method were found to exhibit high anticancer activities, which can lower the viability of cancerous cell lines such as HeLa, MCF-7 and U87.

Davis-Beirut Reaction: A Photochemical Br?nsted Acid Catalyzed Route to N-Aryl 2 H-Indazoles

The Davis-Beirut reaction provides access to 2H-indazoles from aromatic nitro compounds. However, N-aryl targets have been traditionally challenging to access due to competitive alternate reaction pathways. Previously, the key nitroso imine intermediate w

N-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights

A concise, one-step route to indazolones from primary alkyl amines and o-nitrobenzyl alcohols is reported. The key step in this readily scalable indazolone forming process involves base-mediated in situ o-nitrobenzyl alcohol → o-nitrosobenzaldehyde conversion. Although this functional group interconversion is known to be useful for 2H-indazole synthesis, its reactivity was modulated for indazolone formation.

Photochemical Preparation of 1,2-Dihydro-3 H-indazol-3-ones in Aqueous Solvent at Room Temperature

o-Nitrosobenzaldehyde is a reactive intermediate useful in the synthesis of nitrogen heterocycles. Previous strategies for using o-nitrosobenzaldehyde involve its isolation via chromatography and/or formation under harsh conditions. Herein, this intermedi

Inhibition of myeloperoxidase: Evaluation of 2H-indazoles and 1H-indazolones

Myeloperoxidase (MPO) produces hypohalous acids as a key component of the innate immune response; however, release of these acids extracellularly results in inflammatory cell and tissue damage. The two-step, one-pot Davis-Beirut reaction was used to synth

Design, synthesis, and biological evaluation of AT1 angiotensin II receptor antagonists based on the pyrazolo[3,4-b]pyridine and related heteroaromatic bicyclic systems

Novel AT1 receptor antagonists bearing the pyrazolo[3,4-b] pyridine bicyclic heteroaromatic system (or structurally related moieties) were designed and synthesized as the final step of a large program devoted to the development of new antihypertensive agents and to the understanding of the molecular basis of their pharmacodynamic and pharmacokinetic properties. The preliminary pharmacological characterization revealed nanomolar AT1 receptor affinity for several compounds of the series and a potent antagonistic activity in isolated rabbit aortic strip functional assay for 7c and 8a. These results stimulated the study of the biopharmaceutical properties of some selected compounds, which were found to be characterized by a permeability from medium to high. Remarkably, the least permeable 7c showed both permeability and oral bioavailability (80%) higher than losartan, but its terminal half-life was shorter. These results suggest that the permeability is not a limiting factor in the pharmacokinetics of these AT1 receptor antagonists.

Selective synthesis of 2-substituted indazolin-3-ones without N-1 protection

N-2-Alkylation of indazolin-3-ones was performed in neutral conditions. This method represents a direct and efficient entry to a class of compounds having interesting biological activities, avoiding the generally required N-1 protection.