72083-74-0

Basic information

• Product Name: 1H-INDAZOLE-3-CARBONYL CHLORIDE
• Synonyms: 1H-INDAZOLE-3-CARBONYL CHLORIDE
• CAS NO: 72083-74-0
• Molecular Formula: C₈H₅ClN₂O
• Molecular Weight: 180.594
• Mol File: 72083-74-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-INDAZOLE-3-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDAZOLE-3-CARBONYL CHLORIDE(72083-74-0)
• EPA Substance Registry System: 1H-INDAZOLE-3-CARBONYL CHLORIDE(72083-74-0)

Safety Data

• Hazardous Substances Data: 72083-74-0(Hazardous Substances Data)

Usage

Physical state

Colorless to light yellow liquid at room temperature

Reactivity

Highly reactive, particularly in the presence of nucleophiles

Uses

Widely used in organic synthesis as a versatile intermediate for the preparation of various indazole derivatives with potential pharmaceutical and medicinal applications, also used in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals, and as a building block for the production of various types of compounds with diverse biological activities.

Role

Plays an important role in the field of organic synthesis and drug development.

Upstream product

• 4498-67-3 1H-Indazole-3-carboxylic acid 

Downstream Products

• 23765-17-5 1⁽²⁾H-indazole-3-carboxylic acid 2-chloro-anilide 
• 1239843-02-7 5-(1H-indazol-3-yl)-3-phenyl-1,2,4-oxadiazole 
• 1449714-09-3 1-(4-benzamidobenzyl)-1H-indazole-3-carboxamide 
• 1449714-08-2 1-(4-(cyclopropanecarboxamido)benzyl)-1H-indazole-3-carboxamide 
• 1449714-43-5 1-(4-aminobenzyl)-1H-indazole-3-carboxamide 
• 1449714-42-4 1-(4-nitrobenzyl)-1H-indazole-3-carboxamide 
• 1449714-07-1 1-(2-benzamidobenzyl)-1H-indazole-3-carboxamide 
• 1449714-06-0 1-(2-(cyclopropanecarboxamido)benzyl)-1H-indazole-3-carboxamide 
• 1449714-41-3 1-(2-aminobenzyl)-1H-indazole-3-carboxamide 
• 1449714-40-2 1-(2-nitrobenzyl)-1H-indazole-3-carboxamide 
• 1449714-18-4 methyl 2-(1-(3-(4-fluorobenzamido)benzyl)-1H-indazole-3-carboxamido)acetate 
• 1449714-17-3 1-(3-benzamidobenzyl)-N-phenyl-1H-indazole-3-carboxamide 
• 1449714-16-2 1-(3-(cyclopropanecarboxamido)benzyl)-N-phenyl-1H-indazole-3-carboxamide 
• 1449714-33-3 1-(3-(4-acetylbenzamido) benzyl)-1H-indazole-3-carboxamide 

Relevant articles and documents

Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis

Selective methods for introducing protein post-translational modifications (PTMs) within living cells have proven valuable for interrogating their biological function. In contrast to enzymatic methods, abiotic catalysis should offer access to diverse and new-to-nature PTMs. Herein, we report the boronate-assisted hydroxamic acid (BAHA) catalyst system, which comprises a protein ligand, a hydroxamic acid Lewis base, and a diol moiety. In concert with a boronic acid-bearing acyl donor, our catalyst leverages a local molarity effect to promote acyl transfer to a target lysine residue. Our catalyst system employs micromolar reagent concentrations and affords minimal off-target protein reactivity. Critically, BAHA is resistant to glutathione, a metabolite which has hampered many efforts toward abiotic chemistry within living cells. To showcase this methodology, we installed a variety of acyl groups inE. colidihydrofolate reductase expressed within human cells. Our results further establish the well-known boronic acid-diol complexation as abona fidebio-orthogonal reaction with applications in chemical biology and in-cell catalysis.

Synthesis and HepatitisC Antiviral Activity of 1-Aminobenzyl-1H-indazole-3-carboxamide Analogues

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Structure-activity relationship study of EphB3 receptor tyrosine kinase inhibitors

A structure-activity relationship study for a 2-chloroanilide derivative of pyrazolo[1,5-a]pyridine revealed that increased EphB3 kinase inhibitory activity could be accomplished by retaining the 2-chloroanilide and introducing a phenyl or small electron donating substituents to the 5-position of the pyrazolo[1,5-a]pyridine. In addition, replacement of the pyrazolo[1,5-a]pyridine with imidazo[1,2-a]pyridine was well tolerated and resulted in enhanced mouse liver microsome stability. The structure-activity relationship for EphB3 inhibition of both heterocyclic series was similar. Kinase inhibitory activity was also demonstrated for representative analogs in cell culture. An analog (32, LDN-211904) was also profiled for inhibitory activity against a panel of 288 kinases and found to be quite selective for tyrosine kinases. Overall, these studies provide useful molecular probes for examining the in vitro, cellular and potentially in vivo kinase-dependent function of EphB3 receptor.