184031-16-1

Basic information

• Product Name: (1H-INDOL-5-YL)-CARBAMIC ACID TERT-BUTYL ESTER
• Synonyms: 5-BOC-AMINO-1H-INDOLE;5-N-BOC-AMINO-1H-INDOLE;(1H-INDOL-5-YL)-CARBAMIC ACID TERT-BUTYL ESTER;Carbamic acid, N-1H-indol-5-yl-, 1,1-dimethylethyl ester;tert-Butyl 1H-indol-5-ylcarbaMate
• CAS NO: 184031-16-1
• Molecular Formula: C₁₃H₁₆N₂O₂
• Molecular Weight: 232.28
• Mol File: 184031-16-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 350.355 °C at 760 mmHg
• Flash Point: 165.689 °C
• Appearance: /
• Density: 1.217 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: 2-8°C
• PKA: 14.33±0.43(Predicted)
• CAS DataBase Reference: (1H-INDOL-5-YL)-CARBAMIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (1H-INDOL-5-YL)-CARBAMIC ACID TERT-BUTYL ESTER(184031-16-1)
• EPA Substance Registry System: (1H-INDOL-5-YL)-CARBAMIC ACID TERT-BUTYL ESTER(184031-16-1)

Safety Data

• Hazardous Substances Data: 184031-16-1(Hazardous Substances Data)

Usage

General Description

(1H-Indol-5-yl)-carbamic acid tert-butyl ester, also known as indacaterol, is a chemical compound that belongs to the class of indole derivatives. It is commonly used as a bronchodilator in the treatment of chronic obstructive pulmonary disease (COPD) and asthma. Indacaterol works by relaxing the muscles in the airways, allowing for easier breathing. It is marketed under the brand name Onbrez for the management of COPD and has been shown to improve lung function and reduce symptoms of breathlessness. The compound is a white to off-white solid and is typically administered via inhalation in the form of a dry powder or a solution for nebulization.

InChI:InChI=1/C13H16N2O2/c1-13(2,3)17-12(16)15-10-4-5-11-9(8-10)6-7-14-11/h4-8,14H,1-3H3,(H,15,16)

Upstream product

• 5192-03-0 5-amino-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1549940-96-6 N-(3-(2-(4-(4-fluorobenzyl)piperidin-1-yl)-2-oxoacetyl)-1H-indol-5-yl)methanesulfonamide 
• 1549940-93-3 N-(3-(2-(4-(4-fluorobenzyl)piperidin-1-yl)acetyl)-1H-indol-5-yl)methanesulfonamide 
• 1549940-85-3 1-(5-amino-1H-indol-3-yl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethanone 
• 1549940-71-7 tert-butyl 3-(2-(4-(4-fluorobenzyl)piperidin-1-yl)-2-oxoacetyl)-1H-indol-5-ylcarbamate 
• 1549940-55-7 tert-butyl 3-[2-(4-(4-fluorobenzyl)piperidin-1-yl)acetyl]-1H-indol-5-ylcarbamate 

Relevant articles and documents

Synthesis and biological characterization of 3-substituted 1 H -indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors. Part 2

In the course of the identification of new indole derivatives targeting GluN2B-subunit-containing N-methyl-d-aspartate (NMDA) receptor, the (N-1H-indol-6-methanesulfonamide-3-yl)-2-(4-benzylpiperidin-1-yl)ethanone (10b) was identified as a potent ligand for this NMDA receptor subunit. It displays very high binding affinity (IC50 of 8.9 nmol) for displacement of [3H]ifenprodil, thus showing improved potency with respect to the previously reported analogues as confirmed by functional assay. This finding was consistent with the docking pose of compound 10b within the binding pocket localized in the GluN1-GluN2B subunit interface of NMDA receptor tetraheteromeric complex.

Indol-3-yl-tetramethylcyclopropyl ketones: Effects of indole ring substitution on CB2 cannabinoid receptor activity

A series of potent indol-3-yl-tetramethylcyclopropyl ketones have been prepared as CB2 cannabinoid receptor ligands. Two unsubstituted indoles (5, 32) were the starting points for an investigation of the effect of indole ring substitutions on CB2 and CB1 binding affinities and activity in a CB2 in vitro functional assay. Indole ring substitutions had varying effects on CB2 and CB1 binding, but were generally detrimental to agonist activity. Substitution on the indole ring did lead to improved CB2/CB1 binding selectivity in some cases (i.e., 7-9,15-20). All indoles with the morpholino-ethyl side chain (32-43) exhibited weaker binding affinity and less agonist activity relative to that of their tetrahydropyranyl-methyl analogs (5-31). Several agonists were active in the complete Freund's adjuvant model of chronic inflammatory thermal hyperalgesia (32, 15).

HETEROARYLPHENYLUREA DERIVATIVE

The present invention provides a compound represented by the formula (1): wherein R 1 , R 2 and R 5 are each independently selected from a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl is substituted with a halogen atom and the like; R 3 and R 4 are each independently selected from a hydrogen atom, a halogen atom, a substituted C 1 -C 6 alkyl group and the like; R 6 and R 7 are each independently selected from a hydrogen atom and a halogen atom; Z 1 and Z 2 are each independently selected from a hydrogen atom, a hydroxyl group and -O(CHR 11 )OC(=O)R 12 ; Q is a group of the formula: (wherein G 1 is C-Y 2 or N; a ring A is a benzene ring or a 5- to 6-membered unsaturated heterocycle) a pharmaceutically acceptable salt thereof or a prodrug thereof.