197506-83-5

Basic information

• Product Name: 3-FORMYL-1H-INDOLE-5-CARBOXYLIC ACID METHYL ESTER
• Synonyms: RARECHEM AH BS 0103;3-FORMYLINDOLE-5-CARBOXYLIC ACID METHYL ESTER;3-FORMYL-1H-INDOLE-5-CARBOXYLIC ACID METHYL ESTER;METHYL 3-FORMYLINDOLE-5-CARBOXYLATE;METHYL 3-FORMYL-1H-INDOLE-5-CARBOXYLATE;INDOLE-3-ALDEHYDE-5-CARBOXYLIC ACID METHYL ESTER;INDOLE-3-CARBOXALDEHYDE-5-CARBOXYLIC ACID METHYL ESTER;Methyl 3-forMylindole-5-c...
• CAS NO: 197506-83-5
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19
• Product Categories: Indole
• Mol File: 197506-83-5.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 404.4 °C at 760 mmHg
• Flash Point: 198.4 °C
• Appearance: /
• Density: 1.341 g/cm³
• Vapor Pressure: 9.46E-07mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 14.59±0.30(Predicted)
• CAS DataBase Reference: 3-FORMYL-1H-INDOLE-5-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FORMYL-1H-INDOLE-5-CARBOXYLIC ACID METHYL ESTER(197506-83-5)
• EPA Substance Registry System: 3-FORMYL-1H-INDOLE-5-CARBOXYLIC ACID METHYL ESTER(197506-83-5)

Safety Data

• Hazardous Substances Data: 197506-83-5(Hazardous Substances Data)

Usage

General Description

3-Formyl-1H-indole-5-carboxylic acid methyl ester is a chemical compound with the molecular formula C12H11NO3. It is an ester derivative of indole-5-carboxylic acid and is commonly used in organic synthesis and pharmaceutical research. 3-FORMYL-1H-INDOLE-5-CARBOXYLIC ACID METHYL ESTER has been studied for its potential biological activities, including its role as an inhibitor of the enzyme spermine synthase, which is involved in polyamine biosynthesis. Additionally, 3-formyl-1H-indole-5-carboxylic acid methyl ester has been investigated for its potential as a fluorescent probe for detecting zinc ions in biological samples. Overall, this compound has potential applications in the fields of medicinal chemistry and biochemistry, making it an interesting target for further research and development.

InChI:InChI=1/C11H9NO3/c1-15-11(14)7-2-3-10-9(4-7)8(6-13)5-12-10/h2-6,12H,1H3

Upstream product

• 100-97-0 hexamethylenetetramine 
• 1011-65-0 5-methoxycarbonylindole 
• 298-12-4 Glyoxilic acid 
• 1670-81-1 1H-Indole-5-carboxylic acid 
• 100-61-8 N-methylaniline 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 947413-24-3 1-benzyl-N-(diaminomethylene)-3-[(dimethylamino)methyl]-1H-indole-5-carboxamide 
• 194490-33-0 methyl 3-cyano-1H-indole-5-carboxylate 

Relevant articles and documents

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.

Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer

Evodiamine (Evo) is a quinazolinocarboline alkaloid found in Evodia rutaecarpa and exhibits moderate antiproliferative activity. Herein, we report using a scaffold-hopping approach to identify a series of novel polycyclic heterocyclic derivatives based on Evo as the topoisomerase I (Top1) inhibitor for the treatment of triple-negative breast cancer (TNBC), which is an aggressive subtype of breast cancer with limited treatment options. The most potent compound 7f inhibited cell growth in a human breast carcinoma cell line (MDA-MB-231) with an IC50 value of 0.36 μM. Further studies revealed that Top1 was the target of 7f, which directly induced irreversible Top1-DNA covalent complex formation or induced an oxidative DNA lesion through an indirect mechanism mediated by reactive oxygen species. More importantly, in vivo studies showed that 7f exhibited potent antitumor activity in a TNBC-patient-derived tumor xenograft model. These results suggest that compound 7f deserves further investigation as a promising candidate for the treatment of TNBC.

Synthesis of 3-Formylindoles via Electrochemical Decarboxylation of Glyoxylic Acid with an Amine as a Dual Function Organocatalyst

A new method for 3-formalytion of indoles has been developed through electrochemical decarboxylation of glyoxylic acid with the amine as a dual function organocatalyst. The amine facilitated both the electrochemical decarboxylation and the nucleophilic reaction efficiently, whose loading can be as low as 1 mol %. This protocol has a broad range of functional group tolerance under ambient conditions. The gram-scale experiment has shown great potential in the synthetic application of this strategy.