16732-73-3

Usage

Uses

Used in Pharmaceutical Industry:
6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its unique structure allows it to be a key component in the synthesis of a range of drugs with different therapeutic applications.
Used in Chemical Synthesis:
6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID is used as a reactant for demethylation reactions using ionic liquids under microwave irradiation. This process is crucial in the synthesis of various organic compounds, as it allows for the selective removal of the methoxy group, enabling further functionalization and modification of the molecule.
Used in the Synthesis of Pyrazinoindoledione:
6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID is used as a reactant for the preparation of pyrazinoindoledione via Ugi reaction and microwave-assisted cyclization. Pyrazinoindoledione is a class of compounds with potential applications in various fields, including pharmaceuticals and materials science.
Used in the Synthesis of Isoquinolinecarboxamides and their Derivatives:
6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID is used as a reactant for the preparation of isoquinolinecarboxamides and their derivatives, which are known to act as opioid receptor antagonists. These compounds have potential applications in the treatment of pain and addiction.
Used in the Synthesis of Indole Fatty Alcohol Derivatives:
6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID serves as a synthetic intermediate for the preparation of indole fatty alcohol derivatives. These compounds have potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.
Used in the Synthesis of Acylaminoalkylindoles:
6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID is used as a reactant for the preparation of acylaminoalkylindoles as MT2-selective melatonin antagonists. These compounds have potential applications in the treatment of various disorders related to the melatonin receptor, such as sleep disorders, mood disorders, and circadian rhythm disorders.

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

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

Downstream Products

• 15050-04-1 6-methoxy-1H-indole-2-carboxylic acid ethyl ester 
• 3189-13-7 6-methoxylindole 
• 952140-14-6 methyl 3-[(6-methoxyindol-2-yl)carbonyl]-1-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate 
• 952140-60-2 methyl 3-[(6-methoxyindol-2-yl)carbonyl]-1-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate 
• 70555-46-3 6-methoxy-1H-indole-3-carbaldehyde 
• 651331-51-0 6-methoxy-1-(4-methoxybenzenesulfonyl)-1H-indole-3-carbaldehyde 
• 651331-67-8 10-[6-methoxy-1-(4-methoxybenzenesulfonyl)-1H-indol-3-yl]decan-1-ol 
• 651331-76-9 12-[6-methoxy-1-(4-methoxybenzsulfonyl)-1H-indole-3-yl]-dodecane-1-ol 
• 812653-06-8 14-[6-methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-tetradecan-1-ol 
• 812653-07-9 16-[6-methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-hexadecan-1-ol 
• 812653-08-0 18-[6-methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-octadecan-1-ol 
• 143702-32-3 1-benzenesulfonyl-3-bromomethyl-6-methoxyindole 
• 143702-30-1 6-methoxy-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde 
• 143702-31-2 1-benzenesulfonyl-3-hydroxymethyl-6-methoxyindole 

Relevant academic research and scientific papers

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.

N-substituted indole derivative and application thereof

The invention belongs to the technical field of medicine, and relates to an N-substituted indole derivative, pharmaceutically acceptable salts and hydrates thereof, a pharmaceutical composition taking the derivative as an active component, and application

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.

Structure-based design and biological evaluation of novel 2-(indol-2-yl) thiazole derivatives as xanthine oxidase inhibitors

Inhibition of xanthine oxidase (XO) has obviously been a central concept for controlling hyperuricemia, which causes serious and painful inflammatory arthritis disease such as gout. We discovered a series of novel 2-(indol-2-yl)thiazole derivatives as XO inhibitors at the level of nanomolar activity. Structure-guided design using molecular modeling program (Accelrys Software program) provided an excellent basis for optimization of 2-(indol-2-yl)thiazole compounds. Structure-activity relationship indicated that hydrophobic alkoxy group (isopropoxy, cyclopentoxy) at 5-position and hydrogen binding acceptor (NO2, CN) at 7-position of indole ring appear as critical functional groups. Among the compounds, 2-(7-nitro-5-isopropoxy-indol-2-yl)-4-methylthiazole-5-carboxylic acid (9m) exhibits the most potent XO inhibitory activity (IC50value: 5.1 nM) and the excellent uric acid lowering activity in potassium oxonate induced hyperuricemic rat model.

HETEROCYCLIC COMPOUNDS

Heterocyclic compounds and methods of making them and using them.

Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry

Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chemistry, allowing formation of peptide adducts which can be subsequently labeled with fluorine tags.

Synthesis and in vitro opioid receptor functional antagonism of analogues of the selective kappa opioid receptor antagonist (3R)-7-hydroxy-N-((1S)-1- {[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl) -1,2,3,4-tetrahydro-3-is

In previous structure-activity relationship (SAR) studies, we identified (3R)-7-hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1- piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3- isoquinolinecarboxamide (JDTic, 1) as the first poten

INDOLE DERIVATIVES AND DRUGS CONTAINING THE SAME

An indole derivative represented by the following general formula (1) : wherein at least one of R1, R2, R3, and R4 represents an alkoxy group containing 1 to 20 carbon atoms, and other groups of the R1, R2, R3, and R4 represent hydrogen, an alkyl group containing 1 to 6 carbon atoms, acetyl group, or hydroxyl group; and either one of X and Y represents -(CH2)nOH wherein n is an integer of 0 to 30, and the other one of the X and Y represents hydrogen atom; or a salt thereof; and a drug and an agent for promoting differentiation of a stem cell containing such indole derivative or its salt as an effective component. The indole derivative (1) of the present invention has action of inducing differentiation of neural stem cell specifically into a neuron, and this indole derivative is useful as a prophylactic or therapeutic drug for brain dysfunction or neuropathy caused by loss or degeneration of the neuron.

Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheres

In a search for inducers of neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared, 13c (n = 18) was able to promote the differentiation of neural stem cell derived neurospheres into neurons at a concentration of 10 nM. Analysis of the expression of the Notch pathway genes in neurospheres treated during the differentiation phase with 13c (n = 18) revealed a significant decrease in the transcription of the Notch 4 receptor.

USE OF INDOLYL DERIVATIVES FOR THE MANUFACTURE OF A MEDICAMENT FOR THE TREATMENT ALLERGIC RHINITIS

A method to treat allergic rhinitis is disclosed in which patients are administered certain indolyl compounds.