7598-91-6

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE is used as a reactant for the preparation of potential anti-inflammatory and analgesic agents. Its unique chemical structure allows it to modulate biological pathways involved in inflammation and pain relief.
Used in Obesity Treatment:
ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE is used as a reactant for the preparation of histamine-3 receptor inverse agonists. These agents have the potential to treat obesity by modulating histamine signaling pathways, which play a role in appetite regulation and energy metabolism.
Used in Cancer Research:
ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE is useful for the preparation and study of hypoxia-selective cytotoxicity of indolequinone antitumor agents. Its ability to selectively target hypoxic cancer cells makes it a promising candidate for the development of novel cancer therapies.
Used in Tubulin Polymerization Inhibition:
ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE is used as a reactant for the preparation of tubulin polymerization inhibitors. These agents can disrupt the formation of microtubules, which are essential for cell division, and have potential applications in the treatment of various cancers.
Used in Drug Development:
ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE is used as a reactant for the preparation of 4,7-dioxoindole-3-methyl prodrugs. Prodrugs are biologically inactive compounds that are converted into active drugs within the body, allowing for improved drug delivery and reduced side effects.
Used in Muscarinic Receptor Antagonism:
ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE is used as an antagonist at M4 muscarinic receptors. Modulating the activity of these receptors can have therapeutic benefits in various conditions, such as urinary incontinence, overactive bladder, and certain neurological disorders.

InChI:InChI=1/C12H13NO3/c1-3-16-12(15)11-7(2)13-10-5-4-8(14)6-9(10)11/h4-6,13-14H,3H2,1-2H3

Upstream product

• 626-34-6 ethyl aminocrotonate 
• 106-51-4 p-benzoquinone 
• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 
• 626-34-6 ethyl 3-aminobut-2-enoate 
• 1386231-56-6 potassium (4-aminophenyl)trifluoroborate 

Downstream Products

• 101890-42-0 5-benzyloxy-2-methyl-indole-3-carboxylic acid ethyl ester 
• 13314-85-7 2-methyl-1H-indol-5-ol 
• 71982-15-5 5-hydroxy-2-methyl-1H-indole-3-carboxylic acid 
• 32387-22-7 5-methoxy-2methyl-1H-indole-3-carboxylic acid 
• 50995-59-0 2-methyl-4,5-dioxo-3-ethoxycarbonyl-4,5-dihydroindole 
• 20862-91-3 ethyl 5-acetyloxy-2-methyl-1H-indole-3-carboxylate 
• 40963-98-2 ethyl 5-methoxy-1,2-dimethyl-1H-indole-3-carboxylate 
• 16052-67-8 ethyl 6-bromo-5-hydroxy-2-methyl-indole-3-carboxylate 
• 87992-18-5 6H-4-bromo-8-carbethoxy-7-methyl-2-phenyloxazolo<4,5-e>indole 
• 2126032-35-5 ethyl 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-2-(((3-hydroxyphenyl)thio)methyl)-1-methyl-1H-indole-3-carboxylate 
• 842162-68-9 ethyl 6-bromo-5-hydroxy-2-(((3-methoxyphenyl)thio)methyl)-1-methyl-1H-indole-3-carboxylate 
• 131707-24-9 6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester 
• 131707-25-0 arbidol 

Relevant academic research and scientific papers

Preparation method of arbidol key intermediate

The invention discloses a preparation method of an arbidol key intermediate, which belongs to the technical field of drug synthesis. The preparation method comprises the following steps of carrying out bromination reaction on a 4-aminophenylboronic acid derivative 1 and NBS to obtain an intermediate 2, condensing the intermediate 2 and ethyl acetoacetate under the action of an indium catalyst to obtain an intermediate 3, carrying out catalytic cyclization reaction on a copper salt to obtain an intermediate 4, and oxidizing with hydrogen peroxide to obtain the 5-hydroxy-2-methyl-1H-indole-3-ethyl carboxylate 5. The process is simple, convenient and stable to operate, high in yield and environmentally friendly, compared with an existing process, benzoquinone which is high in toxicity and easy to raise is avoided, the production safety risk of an existing arbidol intermediate is greatly reduced, the product purity reaches up to 99.5%, and the single impurity content is lower than 0.1%.

MUSCARINIC ACETYLCHOLINE RECEPTOR SUBTYPE 4 ANTAGONISTS IN THE TREATMENT OF ANEMIA

This disclosure generally relates to treating anemias. More specifically, the disclosure relates to use of muscarinic acetylcholine receptor subtype 4 antagonists, such as small molecule compounds, to promote self-renewal of burst forming unit erythroid (BFU-E) cells and treat anemias.

Indole Based Weapons to Fight Antibiotic Resistance: A Structure-Activity Relationship Study

Antibiotic resistance represents a worldwide concern, especially regarding the outbreak of methicillin-resistant Staphylococcus aureus, a common cause for serious skin and soft tissues infections. A major contributor to Staphylococcus aureus antibiotic resistance is the NorA efflux pump, which is able to extrude selected antibacterial drugs and biocides from the membrane, lowering their effective concentrations. Thus, the inhibition of NorA represents a promising and challenging strategy that would allow recycling of substrate antimicrobial agents. Among NorA inhibitors, the indole scaffold proved particularly effective and suitable for further optimization. In this study, some unexplored modifications on the indole scaffold are proposed. In particular, for the first time, substitutions at the C5 and N1 positions have been designed to give 48 compounds, which were synthesized and tested against norA-overexpressing S. aureus. Among them, 4 compounds have NorA IC50 values lower than 5.0 μM proving to be good efflux pump inhibitor (EPI) candidates. In addition, preliminary data on their ADME (absorption, distribution, metabolism, and excretion) profile is reported.

Manufacturing synthesis of 5-hydroxy-2-methyl-1H-indole

The manufacturing synthesis of 5-hydroxy-2-methyl-1H-indole is described and two synthetic methods were used and the results discussed. Two small and three large runs with Nenitzescu's method were analyzed and results reported with different reaction conditions. Manufacturing issues encountered were discussed. Production scale of more than 60 kg of the 5-hydroxy-2-methyl-1H- indole-3-carboxylic acid ethyl ester and over 20 kg of the 5-hydroxy-2-methyl- 1H-indole were achieved. Based on these results, larger scale manufacturing of this product or similar products based on the optimized conditions is feasible.

A mild and selective method for the N-Boc deprotection by sodium carbonate

A cleavage of N-tert-butyloxycarbonyl protection by Na2CO3 is reported. The N-free products are obtained in excellent yields. The compatibility of the method with the presence of acidic or basic groups is demonstrated. The reactions were performed on indole, azaindole, indazole, pyrazole, indolinone, quinolinone, and oxazolone.

Lewis acid catalyzed Nenitzescu indole synthesis

A novel method for Lewis acid catalyzed Nenitzescu indole syntheses of 5-hydroxyindoles bearing different substituents in positions 1 (Alk, Bn, Ar), 2 (Me, Et, Ph), and 3 (COOEt, COMe, CONHPh) as well as tricyclic derivatives are reported. The method is simple, rapid, efficient, and allows preparation of hydroxyindoles from 1,4-benzoquinone and enamines in good to excellent yields with the use of low-polar solvents in the presence of weak Lewis acids catalysts. The formation of 5-hydroxyindoles under such mild conditions is explained in terms of a non-redox mechanism.

Synthesis of Substituted 1H-3,4-Dihydrodiazepinoindol-3-ones, 3,7-Dihydropyranoindol-7-ones and 6H-Oxazoloindoles

Ethyl 6-substituted 5-hydroxy-2-methylindole-3-carboxylates (1a,b), prepared by Nenitzescu reaction, Vilsmeier-Haack formylation using DMF and POCl3 form the corresponding 4-aldehydes (2a,b).These aldehydes undergo condensation with hydrazine hydrate (80percent) to produce 8-substituted 3,4-dihydro-7-hydroxy-2-methyldiazepinoindol-3-ones (3a,b).The reaction of 2a,b with acetic anhydride and triethylamine under reflux yields 5-substituted 1-carbethoxy-3,7-dihydro-2-methylpyranoindol-7-ones (4a,b).Ethyl 6-substituted 5-hydroxy-2-methyl-4-nitrosoindole-3-carboxylates (5a,b), prepared by nitrosation of 1a,b with acetic acid and sodium nitrite, when refluxed with benzylamine furnish the corresponding 4-substituted 6H-8-carbethoxy-7-methyl-2-phenyloxazoloindoles (6a,b).Following the above sequence of reactions ethyl 5-hydroxy-2-methylbenzindole-3-carboxylate has been converted into 1H-3,4-dihydro-7-hydroxy-2-methylbenzdiazepinoindol-3-one (9), 3-carbethoxy-1,6-dihydro-2-methylbenzpyranoindol-6-one (10) and 6H-4-carbethoxy-5-methyl-2-phenylbenzoxazoloindole (12).

Synthesis of Substituted Oxadiazolylindoles

Indole-3-carboxyhydrazides (2a-d) are prepared and reacted with triethyl orthoformate to yield 3-(1',3',4'-oxadiazol-2'-yl)indoles (4a1-d1). 2a-d on reaction with benzaldehyde yield the corresponding schiff bases (3a-c).These on oxidative cyclodehydrogenation give 3-(5'-phenyl-1',3',4'-oxadiazol-2'-yl)indoles (4a2-d2). 2a-d also react with CS2 to produce 3-(5'-thione-1',3',4'-oxadiazol-2'-yl)indoles (5a-c) which undergo Mannich reaction with formaldehyde and 2-aminothiazoles to yield 7a-d.