4382-54-1

Basic information

• Product Name: 5-METHOXYINDOLE-2-CARBOXYLIC ACID
• Synonyms: TIMTEC-BB SBB003635;1H-Indole-2-carboxylic acid, 5-methoxy-;5-Methoxy-2-indolecarboxylic acid;5-methoxy-2-indolecarboxylicacid;5-methoxy-indole-2-carboxylicaci;Acide methoxy-5 indole carboxylique-2;Indole-2-carboxylic acid, 5-methoxy-;5-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
• CAS NO: 4382-54-1
• Molecular Formula: C₁₀H₉NO₃
• Molecular Weight: 191.18
• EINECS: 224-487-6
• Product Categories: Indole/indoline/oxindole;Indole and Indoline;Indoles and derivatives;Indole;Indoles;Simple Indoles;Boronic Acid;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Building Blocks;C10;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 4382-54-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 199-201 °C(lit.)
• Boiling Point: 326.92°C (rough estimate)
• Flash Point: 224.5 °C
• Appearance: Light yellow to brownish/Powder
• Density: 1.2722 (rough estimate)
• Vapor Pressure: 8.54E-09mmHg at 25°C
• Refractive Index: 1.5310 (estimate)
• Storage Temp.: Refrigerator
• PKA: 4.38±0.30(Predicted)
• BRN: 157478
• CAS DataBase Reference: 5-METHOXYINDOLE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXYINDOLE-2-CARBOXYLIC ACID(4382-54-1)
• EPA Substance Registry System: 5-METHOXYINDOLE-2-CARBOXYLIC ACID(4382-54-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: NL6005000
• HazardClass: IRRITANT
• Hazardous Substances Data: 4382-54-1(Hazardous Substances Data)

Usage

Description

5-Methoxyindole-2-carboxylic acid is a versatile organic compound with a light yellow to brownish powder appearance. It serves as a crucial synthetic intermediate in the development of various pharmaceutical agents and imaging probes.

Uses

Used in Pharmaceutical Industry:
5-Methoxyindole-2-carboxylic acid is used as a reactant for the preparation of various pharmaceutical agents, including:
Anticancer agents: It plays a role in the synthesis of compounds that target cancer cells and inhibit their growth.
Indoleamine 2,3-dioxygenase (IDO) inhibitors: These inhibitors are used to modulate immune responses and have potential applications in cancer therapy.
Potent antitumor bifunctional DNA alkylating agents: These agents are designed to bind and alter DNA, leading to the disruption of cancer cell replication.
Used in Biomedical Research:
5-Methoxyindole-2-carboxylic acid is used as a fluorescent small molecule probe for in vivo lipid imaging, aiding in the visualization and study of lipid metabolism and distribution within living organisms.
Used in Drug Development:
It serves as a reactant for the preparation of:
Selective Dopamine D3 receptor ligands: These ligands are used to study and modulate dopamine receptor activity, with potential applications in the treatment of neurological and psychiatric disorders.
5-HT4 receptor ligands: These ligands target the serotonin 4 receptor, which is involved in various physiological processes, including gastrointestinal motility and cognitive function.
Inhibitors of Mycobacterium tuberculosis pantothenate synthetase: These inhibitors target an enzyme essential for the growth of Mycobacterium tuberculosis, potentially leading to new treatments for tuberculosis.
Hypoxia selective cytotoxins: These compounds are designed to selectively kill cells under low oxygen conditions, such as those found in solid tumors, making them potential candidates for cancer therapy.

InChI:InChI=1/C10H9NO3/c1-14-7-2-3-8-6(4-7)5-9(11-8)10(12)13/h2-5,11H,1H3,(H,12,13)/p-1

Upstream product

• 4792-58-9 ethyl 5-methoxy-1H-indole-2-carboxylate 
• 82204-34-0 (5-methoxy-2-nitro-phenyl)-pyruvic acid 
• 67929-86-6 methyl 5-methoxyindole-2-carboxylate 
• 591-31-1 3-methoxy-benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 4346-59-2 para-methoxyphenyldiazonium chloride 
• 4792-56-7 ethyl 2-(4-methoxyphenylazo)-2-methyl-3-oxobutanoate 
• 4792-57-8 ethyl 2-[2-(4-methoxyphenyl)hydrazinylidene]propanoate 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 124-38-9 carbon dioxide 
• 169383-96-4 2-bromo-5-methoxy-1H-indole 

Downstream Products

• 1006-94-6 5-methoxylindole 
• 104961-45-7 5-methoxy-1-phenyl-1H-indole-2-carboxylic acid 
• 4792-58-9 ethyl 5-methoxy-1H-indole-2-carboxylate 
• 101134-49-0 (5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone 
• 103373-06-4 1,3-Dihydro-3-(RS)-(5-methoxyindole-2-carbonylamino)-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one 
• 62099-65-4 5-methoxyindole-2-carbonyl chloride 
• 160153-70-8 N-phenyl-5-methoxy-1H-2-indolecarboxamide 
• 156638-95-8 5-methoxy-N-methyl-N-phenyl-1H-indole-2-carboxamide 
• 67929-86-6 methyl 5-methoxyindole-2-carboxylate 
• 28837-78-7 N-4-methylperhydro-1-pyrazinyl-5-methoxy-1H-2-indolecarboxamide 
• 855299-72-8 2-[4-(N-benzylamino)-2-(5-methoxyindole-2-carboxamido)naphthalen-1-yl]ethyl acetate 

Relevant articles and documents

Preparation method of indole-2-formic acid derivative

The invention discloses a preparation method of an indole-2-formic acid derivative, wherein the preparation method comprises the steps: by using an oxazolone compound as a raw material, carrying out areaction in an organic solvent at the temperature of 70-150 DEG C under the action of alcohol, alkali and a catalyst, tracking by TLC until the raw material is completely reacted, and separating andpurifying the obtained reaction solution to obtain the indole-2-formic acid derivative. The technology is adopted, the target product indole-2-formic acid derivative is prepared by taking an oxazolonecompound as a raw material through one-pot reaction under the action of alcohol, alkali and a catalyst, so that direct conversion from an oxazolone ring to an indole ring is realized, reaction stepsand an intermediate process are reduced, and the method has the characteristics of cheap raw materials, environmental friendliness and the like, and is suitable for industrial production.

Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway

A series of novel oridonin derivatives bearing various substituents on the 14-OH position were designed and synthesised. Their antitumour activity was evaluated in vitro against three human cancer cell lines (HCT116, BEL7402, and MCF7). Most tested derivatives showed improved anti-proliferative activity compared to the lead compound oridonin and the positive control drug 5-fluorouracil (5-Fu). Among them, compound C7 (IC50 = 0.16 μM) exhibited the most potent anti-proliferative activity against HCT116 cells; it was about 43- and 155-fold more efficacious than that of oridonin (IC50 = 6.84 μM) and 5-Fu (IC50 = 24.80 μM) in HCT116 cancer cells. Interestingly, the IC50 value of compound C7 in L02 normal cells was 23.6-fold higher than that in HCT116 cells; it exhibited better selective anti-proliferative activity and specificity than oridonin and 5-Fu. Furthermore, compound C7 possibly induced cell cycle arrest and apoptosis by regulating the p53-MDM2 signalling pathway. Notably, C7 displayed more significant suppression of tumour growth than oridonin in colon tumour xenograft models where the tumour growth inhibition rate was 85.82%. Therefore, compound C7 could be a potential lead compound for the development of a novel antitumour agent.

Halogen–metal exchange on bromoheterocyclics with substituents containing an acidic proton via formation of a magnesium intermediate

A selective and practical bromine–metal exchange on bromoheterocyclics bearing substituents with an acidic proton under non-cryogenic conditions was developed by a simple modification of an existing protocol. Our protocol of using a combination of i-PrMgCl and n-BuLi has not only solved the problem of intermolecular quenching that often occurred when using alkyl lithium alone as the reagent for halogen–lithium exchange, but also offered a highly selective method for performing bromo–metal exchange on dibrominated arene compounds through chelation effect.