16732-73-3

Basic information

• Product Name: 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
• Synonyms: 1H-INDOLE-2-CARBOXYLIC ACID, 6-METHOXY-;AKOS JY2082559;6-METHOXYINDOLE-2-CARBOXYLIC ACID;6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID;6-Methoxindole-2-Carboxylic Acid;6-Methoxy-1H-indole-2-carboxylic aci;NSC 27988;16732-73-3
• CAS NO: 16732-73-3
• Molecular Formula: C₁₀H₉NO₃
• Molecular Weight: 191.18336
• Product Categories: Indole/indoline/oxindole;Indole and Indoline;Indole;Indoles;Boronic Acid;Heterocyclic Compounds;Building Blocks;C10;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 16732-73-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 198-203℃
• Boiling Point: 447.6 °C at 760 mmHg
• Flash Point: 224.5 °C
• Appearance: /Solid
• Density: 1.381 g/cm³
• Vapor Pressure: 8.54E-09mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly)
• PKA: 4.54±0.30(Predicted)
• CAS DataBase Reference: 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID(16732-73-3)
• EPA Substance Registry System: 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID(16732-73-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 16732-73-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 16732-73-3 differently. You can refer to the following data:
1. ? ;Reactant for demethylation reactions using ionic liquids under microwave irradiation1? ;Reactant for preparation of pyrazinoindoledione via Ugi reaction and microwave-assisted cyclization2? ;Reactant for preparation of isoquinolinecarboxamides and their derivatives as opioid receptor antagonists3? ;Synthetic intermediate for preparation of indole fatty alcohol derivatives4? ;Reactant for preparation of acylaminoalkylindoles as MT2-selective melatonin antagonists5
2. Reactant for demethylation reactions using ionic liquids under microwave irradiationReactant for preparation of pyrazinoindoledione via Ugi reaction and microwave-assisted cyclizationReactant for preparation of isoquinolinecarboxamides and their derivatives as opioid receptor antagonistsSynthetic intermediate for preparation of indole fatty alcohol derivativesReactant for preparation of acylaminoalkylindoles as MT2-selective melatonin antagonists

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

Upstream product

• 3189-13-7 6-methoxylindole 
• 124-38-9 carbon dioxide 
• 123-11-5 4-methoxy-benzaldehyde 
• 143702-29-8 2-azido-3-(4'-methoxyphenyl)acrylic acid methyl ester 
• 98081-83-5 methyl 6-methoxy-1H-indole-2-carboxylate 
• 16792-46-4 (4-methoxy-2-nitro-phenyl)-pyruvic acid 
• 24513-03-9 (Z)-ethyl 2-azido-3-(4-methoxyphenyl)acrylate 
• 15384-39-1 (3-methoxyphenyl)hydrazine 
• 536-90-3 m-Anisidine 
• 98081-75-5 2-azido-3-(4-methoxyphenyl)acrylic acid methyl ester 
• 15050-04-1 6-methoxy-1H-indole-2-carboxylic acid ethyl ester 
• 17484-36-5 4-Methyl-3-nitroanisole 
• 2042-14-0 4-methyl-5-nitrophenol 

Downstream Products

• 15050-04-1 6-methoxy-1H-indole-2-carboxylic acid ethyl ester 
• 3189-13-7 6-methoxylindole 
• 812653-08-0 18-[6-methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-octadecan-1-ol 
• 812653-07-9 16-[6-methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-hexadecan-1-ol 
• 812653-06-8 14-[6-methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-tetradecan-1-ol 

Relevant articles and documents

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.

Discovery and structure-activity relationship studies of N-substituted indole derivatives as novel Mcl-1 inhibitors

Myeloid cell leukemia-1 (Mcl-1) is an important antiapoptotic protein functioning through protein-protein interactions. We discovered LSL-A6 (2-((2-carbamoyl-1-(3-(4-methoxyphenoxy)propyl)-1H-indol-6-yl)oxy)acetic acid) with a novel N-substituted indole scaffold to interfere Mcl-1 binding as a novel Mcl-1 inhibitor. Molecular modeling indicated that this compound binds with Mcl-1 by interaction with P2 and R263 hot-spots. Structure modification focused on several moieties including indole core, hydrophobic tail and acidic chain were conducted and structure-activity relationship was analyzed. The most potent compound 24d which exhibited Ki value of 110?nM for interfering Mcl-1 binding was obtained after hit-to-lead modification.

HETEROCYCLIC COMPOUNDS

Heterocyclic compounds and methods of making them and using them.