10242-02-1

Basic information

• Product Name: 5-METHYL-1H-INDOLE-3-CARBOXYLIC ACID
• Synonyms: 5-Methylindole-3-forMicacid;5-Methyl-3-indole acid;5-METHYLINDOLE-3-CARBOXYLIC ACID;5-METHYL-1H-INDOLE-3-CARBOXYLIC ACID;RARECHEM AL BE 0707;1H-Indole-3-carboxylic acid, 5-methyl-
• CAS NO: 10242-02-1
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Mol File: 10242-02-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 202 °C
• Boiling Point: 421.2 °C at 760 mmHg
• Flash Point: 208.5 °C
• Appearance: /
• Density: 1.34 g/cm³
• Vapor Pressure: 7.58E-08mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: 2-8°C
• PKA: 3.98±0.30(Predicted)
• CAS DataBase Reference: 5-METHYL-1H-INDOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-1H-INDOLE-3-CARBOXYLIC ACID(10242-02-1)
• EPA Substance Registry System: 5-METHYL-1H-INDOLE-3-CARBOXYLIC ACID(10242-02-1)

Safety Data

• Hazardous Substances Data: 10242-02-1(Hazardous Substances Data)

Usage

General Description

5-Methyl-1H-indole-3-carboxylic acid, also known as MICA, is a chemical compound with the molecular formula C11H9NO2. It is a derivative of indole, a heterocyclic compound commonly found in various natural products and pharmaceuticals. MICA is a carboxylic acid containing a methyl substituent at the 5-position of the indole ring. 5-METHYL-1H-INDOLE-3-CARBOXYLIC ACID has been studied for its potential applications in the pharmaceutical industry, particularly as a building block for the synthesis of bioactive compounds and pharmaceutical ingredients. Its unique structure and properties make it a valuable starting material for the development of new drugs and other biologically active molecules.

InChI:InChI=1/C10H9NO2/c1-6-2-3-9-7(4-6)8(5-11-9)10(12)13/h2-5,11H,1H3,(H,12,13)

Upstream product

• 227960-12-5 methyl 5-methyl-1H-indole-3-carboxylate 
• 124-38-9 carbon dioxide 
• 614-96-0 5-methyl-1H-indole 
• 858515-93-2 2,2,2-trifluoro-1-(5-methyl-1H-indol-3-yl)-ethanone 
• 15719-64-9 methylammonium carbonate 

Downstream Products

• 858515-40-9 C₃₂H₄₁N₃O₅ 
• 614-96-0 5-methyl-1H-indole 
• 1404619-67-5 C₃₁H₃₆N₆O₃ 
• 1404536-38-4 C₃₂H₃₅F₃N₆O₃ 

Relevant articles and documents

Design and synthesis of indoleamine 2,3-dioxygenase 1 inhibitors and evaluation of their use as anti-tumor agents

Indoleamine 2,3-dioxygenase (IDO) 1 is the key enzyme for regulating tryptophan metabolism and is an important target for interrupting tumor immune escape. In this study, we designed four series of compounds as potential IDO1 inhibitors by attaching various fragments or ligands to indole or phenylimidazole scaffolds to improve binding to IDO1. The compounds were synthesized and their inhibitory activities against IDO1 and tryptophan 2,3-dioxygenase were evaluated. The cytotoxicities of the compounds against two tumor cell lines were also determined. Two compounds with a phenylimidazole scaffold (DX-03-12 and DX-03-13) showed potent IDO1 inhibition with IC50 values of 0.3–0.5 μM. These two IDO1 inhibitors showed low cell cytotoxicity, which indicated that they may exert their anti-tumor effect via immune modulation. Compound DX-03-12 was investigated further by determining the in vivo pharmacokinetic profile and anti-tumor efficacy. The pharmacokinetic study revealed that DX-03-12 had satisfactory properties in mice, with rapid absorption, moderate plasma clearance (～36% of hepatic blood flow), acceptable half-life (～4.6 h), and high oral bioavailability (～96%). Daily oral administration of 60 mg/kg of compound DX-03-12 decreased tumor growth by 72.2% after 19 days in a mouse melanoma cell B16-F10 xenograft model compared with the untreated control. Moreover, there was no obvious weight loss in DX-03-12-treated mice. In conclusion, compound DX-03-12 is a potent lead compound for developing IDO1 inhibitors and anti-tumor agents.

N -[6-(4-Butanoyl-5-methyl-1 H -pyrazol-1-yl)pyridazin-3-yl]-5-chloro-1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1 H -indole-3-carboxamide (SAR216471), a Novel Intravenous and Oral, Reversible, and Directly Acting P2Y12 Antagonist

In the search of a potential backup for clopidogrel, we have initiated a HTS campaign designed to identify novel reversible P2Y12 antagonists. Starting from a hit with low micromolar binding activity, we report here the main steps of the optimization process leading to the identification of the preclinical candidate SAR216471. It is a potent, highly selective, and reversible P2Y12 receptor antagonist and by far the most potent inhibitor of ADP-induced platelet aggregation among the P2Y12 antagonists described in the literature. SAR216471 displays potent in vivo antiplatelet and antithrombotic activities and has the potential to differentiate from other antiplatelet agents.

NOVEL INDOL CARBOXYLIC ACID BISPYRIDYL CARBOXAMIDE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PREPARATION METHOD AND COMPOSITION CONTAINING THE SAME AS AN ACTIVE INGREDIENT

Disclosed herein are a new indole carboxylic acid bispyridyl carboxamide derivative, a preparation method thereof, and a composition for prevention or treatment of obesity, urinary disorders, and CNS disorders, containing the same as an active ingredient. Because the indole carboxylic acid bispyridyl carboxamide derivatives according to the present invention have high affinity for 5-HT2c receptors, act selectively on the 5-HT2c receptors, the derivatives rarely have adverse effects caused by other receptors. Because the derivatives effectively inhibit serotonin activity, they may be useful for treatment or prevention of obesity; urinary disorders such as urinary incontinence, premature ejaculation, erectile dysfunction, and prostatic hyperplasia; CNS disorders such as depression, anxiety, concern, panic disorder, epilepsy, obsessive-compulsive disorder, migraine, sleep disorder, withdrawal from drug abuse, Alzheimer's disease, and schizophrenia, associated with 5-HT2c receptors.