858515-65-8

Basic information

• Product Name: 4-METHYLINDOLE-3-CARBOXYLIC ACID
• Synonyms: 4-METHYLINDOLE-3-CARBOXYLIC ACID;4-Methyl-1H-indole-3-carboxylic acid
• CAS NO: 858515-65-8
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Mol File: 858515-65-8.mol

Chemical Properties

• Melting Point: 189 °C(Solv: acetone (67-64-1))
• Boiling Point: 419.9°C at 760 mmHg
• Flash Point: 207.8°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 8.41E-08mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.93±0.10(Predicted)
• CAS DataBase Reference: 4-METHYLINDOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLINDOLE-3-CARBOXYLIC ACID(858515-65-8)
• EPA Substance Registry System: 4-METHYLINDOLE-3-CARBOXYLIC ACID(858515-65-8)

Safety Data

• Hazardous Substances Data: 858515-65-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-METHYLINDOLE-3-CARBOXYLIC ACID is used as a precursor in the pharmaceutical industry for the synthesis of various organic compounds. Its unique structure and functional group contribute to the development of new drug molecules, particularly those with potential anti-inflammatory and immunomodulatory effects.
Used in Drug Development:
In the field of drug development, 4-METHYLINDOLE-3-CARBOXYLIC ACID serves as a building block for creating innovative therapeutic agents. Its potential properties are being studied to enhance the treatment of various conditions, highlighting its importance in advancing pharmaceutical research.
Used in Biosynthesis of Natural Products:
4-METHYLINDOLE-3-CARBOXYLIC ACID is also utilized in the biosynthesis of natural products, playing a crucial role in the production of compounds found in nature. This application underscores its versatility and the breadth of its potential impact across different areas of chemistry and biology.
Used in Synthesis of Heterocyclic Compounds:
In the synthesis of heterocyclic compounds, 4-METHYLINDOLE-3-CARBOXYLIC ACID is employed as a key component. Its presence in these reactions allows for the creation of a diverse range of heterocyclic structures, which are vital in various chemical and pharmaceutical applications.

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

Upstream product

• 16096-32-5 4-methyl-1H-indole 
• 15719-64-9 methylammonium carbonate 
• 79878-01-6 4-methyl-3-trifluoroacetylindole 
• 858515-77-2 methyl 4-methyl-1H-indole-3-carboxylate 

Downstream Products

• 858515-39-6 C₃₂H₄₁N₃O₅ 

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.

Design, synthesis, and biological activity of potent and selective inhibitors of mast cell tryptase

A new series of novel mast cell tryptase inhibitors is reported, which features the use of an indole structure as the hydrophobic substituent on a m-benzylaminepiperidine template. The best members of this series display good in vitro activity and excellent selectivity against other serine proteases.