103781-89-1

Basic information

• Product Name: METHYL 6-BENZYLOXYINDOLE-2-CARBOXYLATE
• Synonyms: METHYL 6-BENZYLOXYINDOLE-2-CARBOXYLATE;Methyl 6-(benzyloxy)
• CAS NO: 103781-89-1
• Molecular Formula: C₁₇H₁₅NO₃
• Molecular Weight: 281.31
• Mol File: 103781-89-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 472.3°C at 760 mmHg
• Flash Point: 239.5°C
• Appearance: /
• Density: 1.253g/cm³
• Vapor Pressure: 4.31E-09mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL 6-BENZYLOXYINDOLE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 6-BENZYLOXYINDOLE-2-CARBOXYLATE(103781-89-1)
• EPA Substance Registry System: METHYL 6-BENZYLOXYINDOLE-2-CARBOXYLATE(103781-89-1)

Safety Data

• Hazardous Substances Data: 103781-89-1(Hazardous Substances Data)

Usage

General Description

Methyl 6-benzyloxyindole-2-carboxylate is a chemical compound with the molecular formula C20H17NO3. It is an ester derived from 6-benzyloxyindole-2-carboxylic acid and methanol. METHYL 6-BENZYLOXYINDOLE-2-CARBOXYLATE is commonly used in organic synthesis and medicinal chemistry, as it can serve as a precursor for the preparation of various indole-based compounds. It is also known for its potential pharmacological activities, and its derivatives have been studied for their anti-proliferative, anti-inflammatory, and anti-cancer properties. Additionally, it has shown promising results in the development of novel drugs for neurological disorders. Therefore, methyl 6-benzyloxyindole-2-carboxylate is a versatile and important compound in the field of drug discovery and development.

InChI:InChI=1/C17H15NO3/c1-20-17(19)16-9-13-7-8-14(10-15(13)18-16)21-11-12-5-3-2-4-6-12/h2-10,18H,11H2,1H3

Upstream product

• 4397-53-9 p-benzyloxybenzaldehyde 
• 115663-17-7 methyl α-azido-4-(benzyloxy)cinnamate 

Downstream Products

• 933474-42-1 6-benzyloxy-1-methyl-1H-indole-2-carboxylic acid 
• 933474-43-2 C₂₉H₃₀N₂O₂ 
• 1620658-46-9 1-allyl-6-benzyloxy-1H-indole-2-carboxylic acid 
• 1620658-49-2 7-benzyloxy-10-Iodo-3-(iodomethyl)-3,4-dihydro-1H-[1,4]oxazino[4,3-a]indol-1-one 
• 1620658-53-8 8-benzyloxy-4-hydroxy-11-iodo-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-one 
• 1620658-43-6 methyl 1-allyl-6-benzyloxy-1H-indole-2-carboxylate 
• 1362861-22-0 methyl 6-(benzyloxy)-3-(2,4-bis(methoxymethoxy)phenyl)-1H-indole-2-carboxylate 
• 1362861-21-9 methyl 3-(2,5-dimethoxyphenyl)-6-(benzyloxy)-1H-indole-2-carboxylate 
• 1362860-98-7 methyl 3-iodo-6-(benzyloxy)-1H-indole-2-carboxylate 
• 1362861-45-7 methyl 6-(benzyloxy)-3-(2,4-bis(benzyloxy)phenyl)-1H-indole-2-carboxylate 
• 115663-19-9 3-(6-benzyloxyindol-2-ylcarbonyl)-4,5-dihydro-3-methylfuran-2-one 
• 115663-20-2 1-(6-benzyloxyindol-2-yl)-4-hydroxy-2-methylbutan-1-one 
• 103763-42-4 4-hydroxy-1-(6-benzyloxyindol-2-yl)butan-1-one 
• 103763-36-6 7-benzyloxy-1-methoxy-9H-carbazole 

Relevant articles and documents

Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: A novel DYRK1A inhibitor class

A library of substituted chromeno[3,4-b]indoles was developed as Lamellarin isosters. Synthesis was achieved from indoles after a four-step pathway sequence involving C-3 iodination, a Suzuki cross-coupling reaction, and a one pot deprotection/lactonisation step. Twenty final compounds were tested in order to determine their activity against topoisomerase I and kinases, the two major biological activities of Lamellarins. One newly synthesized derivative exhibited a strong topoisomerase activity comparable to reference compounds such as campthotecin and Lamellarin with only a weak kinase inhibition. Two other lead compounds were identified as new nanomolar DYRK1A inhibitors and several other drugs affected the kinases in the sub-micromolar range. These results will enable us to use the chromeno[3,4-b]indole as a pharmacophore to develop potent treatments for neurological or oncological disorders in which DYRK1A is fully involved.

Oxidative Coupling of Methyl 6-Hydroxyindole-2-carboxylate with Primary Amines: Preparation of 2-Substituted Methyl Pyrrolobenzoxazole-5-carboxylates

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