108438-43-3

Basic information

• Product Name: 1-methylindole-3-carboxylic acid methyl ester
• Synonyms: 1-methylindole-3-carboxylic acid methyl ester;1H-Indole-3-carboxylic acid, 1-Methyl-, Methyl ester;Methyl-N-Methylindole-3-Carboxylate;1-Methyl-1H-indole-3-carboxylic acid methyl ester
• CAS NO: 108438-43-3
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189
• Mol File: 108438-43-3.mol
• Article Data: 33

Chemical Properties

• Melting Point: 87.6-88.7 °C
• Boiling Point: 320.2°C at 760 mmHg
• Flash Point: 147.4°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 0.000323mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-methylindole-3-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methylindole-3-carboxylic acid methyl ester(108438-43-3)
• EPA Substance Registry System: 1-methylindole-3-carboxylic acid methyl ester(108438-43-3)

Safety Data

• Hazardous Substances Data: 108438-43-3(Hazardous Substances Data)

Usage

General Description

1-Methylindole-3-carboxylic acid methyl ester is a chemical compound that belongs to the classes of compounds known as Indoles, specifically Methylindoles. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. They are derived from and include indole itself. Methyl esters are carboxylic acid esters where the parent acid is a simple carboxylic acid and the esterifying group is methyl. This chemical compound is primarily used for research purposes in the fields of organic chemistry, medicinal chemistry, and material science, among others. Details regarding its physical properties, such as its melting and boiling points, its molecular weight, and other specific details will change depending upon its degree of purity, its state, and other specific conditions.

InChI:InChI=1/C11H11NO2/c1-12-7-9(11(13)14-2)8-5-3-4-6-10(8)12/h3-7H,1-2H3

Upstream product

• 1014697-44-9 methyl 3-[N-(2-iodophenyl)-N-methylamino]propionate 
• 603-76-9 1-methylindole 
• 124-38-9 carbon dioxide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67-56-1 methanol 
• 32387-21-6 1-methyl-3-indolecarboxylic acid 
• 942-24-5 3-methoxycarbonylindole 
• 77-78-1 dimethyl sulfate 
• 124-41-4 sodium methylate 
• 151621-88-4 2,2,2-trichloro-1-(1-methyl-1H-indol-3-yl)ethan-1-one 
• 698-01-1 1-chloro-2-(dimethylamino)benzene 
• 120-72-9 indole 
• 487-89-8 Indole-3-carboxaldehyde 
• 558-13-4 carbon tetrabromide 

Relevant articles and documents

Discovery of new indole-based 1,2,4-triazole derivatives as potent tubulin polymerization inhibitors with anticancer activity

Thirty-six novel indole-based 1,2,4-triazole derivatives were designed and synthesized through the molecular hybrid strategy. The bioassay results revealed that 9p displayed excellent antiproliferative efficacies in the nanomolar range against HeLa cells. Importantly, the compound exhibited no obvious cytotoxic activity (IC50 > 100 μM) toward HEK-293, a normal human embryonic kidney cell line. Mechanism analysis indicated that 9p significantly arrested the cell cycle at the G2/M phase and induced apoptosis in HeLa cells in a dose-dependent manner. Further evidence demonstrated that the promising compound effectively inhibited tubulin polymerization with an IC50 value of 8.3 μM, and molecular docking studies revealed that 9p well occupied the colchicine-site in tubulin. The present study highlights that indole-triazole hybrids might be used as a promising scaffold to develop novel tubulin polymerization inhibitors for cancer treatment.

Discovery of novel indole-1,2,4-triazole derivatives as tubulin polymerization inhibitors

A series of novel indole-1,2,4-triazole derivatives have been designed, synthesized, and evaluated as potential tubulin polymerization inhibitors. The top hit 12, bearing the 3,4,5-trimethoxyphenyl moiety, exhibited substantial anti-proliferative activity against HepG2, HeLa, MCF-7, and A549 cells in vitro with IC50 values of 0.23 ± 0.08 μM, 0.15 ± 0.18 μM, 0.38 ± 0.12 μM, and 0.30 ± 0.13 μM, respectively. It also inhibited tubulin polymerization with the IC50 value of 2.1 ± 0.12 μM, which was comparable with that of the positive controls. Furthermore, compound 12 regulated the expression of cell cycle-related proteins (Cyclin B1, Cdc25c, and Cdc2) and apoptosis-related proteins (Bcl-2, Bcl-x, and Mcl-1). Mechanistically, compound 12 could arrest cell cycle at the G2/M phase, thus induce an increase of apoptotic cell death. In addition, molecular docking hinted the possible interaction mode of compound 12 into the colchicine binding site of tubulin heterodimers. According to the applications of microtubule-targeting agents in both direct and synergistic cancer therapies, we hope this work might be of significance for future researches.

Synthesis, anticancer evaluation and molecular docking studies of 2,5-bis(indolyl)-1,3,4-oxadiazoles, Nortopsentin analogues

A series of ten novel 2,5-bis(indolyl)-1,3,4-oxadiazoles were designed and synthesized. All these compounds were evaluated for their cytotoxicity against four cancer cell lines namely A549, MDA-MB-231, MCF-7 and HeLa using MTT reduced assay. Among them, compound 12e exhibited good cytotoxicity on MCF-7 cell line with IC50 value of 1.8 μM and it was identified as a promising drug lead when compared to the standard drug doxorubicin (IC50 value 0.98 μM). Compound, 12h exhibited better antitumor activity against three cancer cell lines i.e., lung (A549), breast (MCF-7) and cervical (HeLa) with IC50 values of 3.3 μM, 2.6 μM and 6.34 μM respectively. The impact of these compounds on colchicine binding site of tubulin polymer was carefully investigated using molecular docking studies and interpretations between actives and inactive were explained.