7598-91-6

Basic information

• Product Name: ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE
• Synonyms: ETHYL 5-HYDROXYMETHYL-2-INDOLE-3-CARBOXYLATE;2171-Antibiotic;2-Methyl-5-hydroxy-1H-indole-3-carboxylic acid ethyl ester;Madumitsin;Madumycin;Mecarbin;Ethyl 5-hydroxy-2-methylindole-3-carboxylate,99%;NSC 405600
• CAS NO: 7598-91-6
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• EINECS: 231-507-7
• Product Categories: Indoles and derivatives;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 7598-91-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 205-208 °C(lit.)
• Boiling Point: 360.05°C (rough estimate)
• Flash Point: 199.7 °C
• Appearance: off-white to light tan crystalline powder
• Density: 1.1825 (rough estimate)
• Vapor Pressure: 3.4E-07mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE(7598-91-6)
• EPA Substance Registry System: ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE(7598-91-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 7598-91-6(Hazardous Substances Data)

Usage

Chemical Properties

off-white to light tan crystalline powder

Uses

Different sources of media describe the Uses of 7598-91-6 differently. You can refer to the following data:
1. Ethyl 5-Hydroxy-2-methyl-1H-indole-3-carboxylate is useful for preparation and study of hypoxia-selective cytotoxicity of indolequinone antitumor agents.
2. Reactant for preparation of:Potential anti-inflammatory and analgesic agentsHistamine-3 receptor inverse agonists for the treatment of obesityTubulin Polymerization Inhibitors4,7-dioxoindole-3-methyl prodrugsAntagonists at M4 muscarinic receptors

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

Downstream Products

• 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 
• 13314-85-7 2-methyl-1H-indol-5-ol 
• 15574-49-9 mecarbinate 
• 34572-31-1 ethyl 5-methoxy-2-methyl-1H-indole-3-carboxylate 
• 110543-98-1 5-acetoxy-6-bromo-2-bromomethyl-1-methylindole-3-carboxylic acid ethyl ester 
• 131707-25-0 arbidol 
• 131707-24-9 6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester 
• 842162-68-9 ethyl 6-bromo-5-hydroxy-2-(((3-methoxyphenyl)thio)methyl)-1-methyl-1H-indole-3-carboxylate 
• 2126032-35-5 ethyl 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-2-(((3-hydroxyphenyl)thio)methyl)-1-methyl-1H-indole-3-carboxylate 

Relevant articles and documents

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%.

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.

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.