620175-74-8

Basic information

• Product Name: 4-METHOXY-1-METHYL-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: 4-METHOXY-1-METHYL-1H-INDOLE-3-CARBALDEHYDE;4-methoxy-1-methyl-1H-Indole-3-carboxaldehyde;1H-Indole-3-carboxaldehyde, 4-methoxy-1-methyl-;4-methoxy-1-methylindole-3-carbaldehyde
• CAS NO: 620175-74-8
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.213
• Mol File: 620175-74-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 357.855°C at 760 mmHg
• Flash Point: 170.225°C
• Appearance: /
• Density: 1.144g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-METHOXY-1-METHYL-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-1-METHYL-1H-INDOLE-3-CARBALDEHYDE(620175-74-8)
• EPA Substance Registry System: 4-METHOXY-1-METHYL-1H-INDOLE-3-CARBALDEHYDE(620175-74-8)

Safety Data

• Hazardous Substances Data: 620175-74-8(Hazardous Substances Data)

Usage

General Description

4-Methoxy-1-methyl-1H-indole-3-carbaldehyde is a chemical compound with the molecular formula C11H11NO2. It is a yellow crystalline powder with a molecular weight of 189.21 g/mol. 4-METHOXY-1-METHYL-1H-INDOLE-3-CARBALDEHYDE is an aldehyde derivative of indole, which is a heterocyclic aromatic organic compound. It is often used as an intermediate in the synthesis of pharmaceuticals, dyes, and other organic compounds. Its chemical properties make it a valuable building block for the production of various pharmaceutical and industrial products.

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

Upstream product

• 90734-97-7 4-methoxyindole-3-carboxaldehyde 
• 74-88-4 methyl iodide 
• 7556-35-6 4-methoxy-1-methyl-1H-indole 
• 75-50-3 trimethylamine 
• 4837-90-5 4-methoxy-1H-indole 

Relevant articles and documents

Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles

A Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles was achieved, affording a variety of multifunctional 3-ylideneoxindoles with good yields andZ/Eselectivities (64%-89% yield, 78?:?22->99?:?1Z/E). Importantly, an operationally simple, one-pot sequential catalytic synthesis of 3-ylideneoxindoles was also developed. Additionally, a cross [1,3]-rearrangement experiment and nonracemic transformation were also carried out, which indicated a concerted rearrangement mechanism of this methodology.

Synthesis and evaluation of selenium-containing indole chalcone and diarylketone derivatives as tubulin polymerization inhibition agents

Sixteen new selenium-containing indole chalcone and diarylketone derivatives were synthesized and evaluated as tubulin polymerization inhibitors. Among them, compound 25b exhibited the most potent antiproliferative activities against six human cancer cell lines with IC50 values of 0.004-0.022 μM. A microtubule dynamics assay and an immunofluorescence assay confirmed that 25b could effectively inhibit tubulin polymerization (IC50 = 2.1 ± 0.27 μM). Further cellular mechanism studies revealed that 25b induced G2/M phase arrest, which was further evidenced by the decrease in the mitochondrial membrane potential (MMP).

Synthesis, biological evaluation and mechanism study of chalcone analogues as novel anti-cancer agents

A series of novel chalcone analogues were designed, synthesized and evaluated as anticancer agents. The results of antiproliferative activity tests showed that most of the analogues exhibited moderate to very good antiproliferative activities with GI50 values in the micromol to sub-micromol range. Especially compound 10a gave 0.026 μM to 0.035 μM GI50 for five cancer cell lines. The mechanistic studies including tubulin polymerization inhibition, disruption of microtubule dynamics and cell cycle arrest assay demonstrated that compound 10a could effectively inhibit in vitro cellular tubulin polymerization, interfere with the mitosis, resulting in a prolonged G2/M cell cycle arrest and ultimately lead to cell apoptosis of cancer cells. Taken together, these results suggested that 10a may became a promising lead compound for development of new anticancer drugs.