1201-24-7

Usage

InChI:InChI=1/C9H8N2O2/c1-5-2-3-7-6(4-5)8(9(12)13)11-10-7/h2-4H,1H3,(H,10,11)(H,12,13)

Upstream product

• 608-05-9 5-methyl-indole-2,3-dione 
• 10501-70-9 1-benzylideneamino-5-methyl-indole-2,3-dione 
• 100-52-7 benzaldehyde 
• 1858-99-7 benzaldehyde p-tolylhydrazone 

Downstream Products

• 1776-37-0 5-methyl-1H-indazole 
• 15719-64-9 methylammonium carbonate 
• 660823-02-9 5-methyl-1H-indazole-3-carboxylic acid (4-fluorophenyl)amide 
• 1908-01-6 3-ethoxycarbonyl-5-methyl-1H-indazole 
• 1448314-58-6 5-methyl-1-(3-methylbenzoyl)-1H-indazole-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthetic method of 5-substituted indazole-3-carboxylic acid

The invention provides a synthesis method of 5-substituted indazole-3-carboxylic acid, and belongs to the field of pharmaceutical chemical synthesis, wherein R=hydrogen, alkyl, alkoxy, trifluoroalkoxyand halogen. A phenylhydrazine compound 3 is taken as a

Optimization of N-benzoylindazole derivatives as inhibitors of human neutrophil elastase

Human neutrophil elastase (HNE) is an important therapeutic target for treatment of pulmonary diseases. Previously, we identified novel N-benzoylindazole derivatives as potent, competitive, and pseudoirreversible HNE inhibitors. Here, we report further development of these inhibitors with improved potency, protease selectivity, and stability compared to our previous leads. Introduction of a variety of substituents at position 5 of the indazole resulted in the potent inhibitor 20f (IC50 ～10 nM) and modifications at position 3 resulted the most potent compound in this series, the 3-CN derivative 5b (IC50 = 7 nM); both derivatives demonstrated good stability and specificity for HNE versus other serine proteases. Molecular docking of selected N-benzoylindazoles into the HNE binding domain suggested that inhibitory activity depended on geometry of the ligand-enzyme complexes. Indeed, the ability of a ligand to form a Michaelis complex and favorable conditions for proton transfer between Hys57, Asp102, and Ser195 both affected activity.

Practical synthesis of 3-carboxyindazoles

A clean, high-yielding synthetic route to methyl 5-(bromomethyl)-1- tritylindazole 3-carboxylate 1 was needed. A principal intermediate was 5-methyl-3-carboxyindazole 2. An analysis of a by-product found after executing Schad's 3-carboxyindazole synthesis led to undertaking this reaction with an inverse addition in the principal step. This simple modification gave 2 in excellent and reproducible yields. Copyright Taylor & Francis, Inc.