Chemical Properties
light beige crystalline powder (recrystallized from acetate-petroleum ether). Soluble in ethanol, ether, acetate, insoluble in boiling water, benzene, insoluble in petroleum ether.
Application
Indole-3-carboxylic Acid is a specific and competitive inhibitor of the potentiation of glycine of NMDA-gated current. Chemical reagent in the synthesis of thiadiazole derivatives used for anticancer activity.
Uses
Indole-3-carboxylic acid is used as a raw material in synthesis. It is useful for the synthesis of anticancer agents, serotonin receptor antagonists, primary acylureas, and amino acid derivatives.Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite and has been found elevated in patients with liver diseases.
Uses
Reactant for preparation of:
Anticancer agents
Derivatives of amino acids and peptides
Serotonin 5-HT4 receptor antagonists
Primary acylureas
Inhibitors of Gli1-mediated transcription in the Hedgehog pathway
Serotonin 5-HT6 antagonists
Very Late Antigen-4 (VLA-4) sntagonists
EphB3 receptor tyrosine kinase inhibitors
Potential Therapeutic Agent for Alzheimer′s Disease
Vinyl ester pseudotripeptide proteasome inhibitors
Definition
ChEBI: Indole-3-carboxylic acid is an indole-3-carboxylic acid carrying a carboxy group at position 3. It has a role as a human metabolite and a bacterial metabolite. It is a conjugate acid of an indole-3-carboxylate.
Preparation
indole-3-carboxylic acid can be synthesized by the hydrolysis reaction of 3-trichloroacetyl indole: add 235g 3-trichloroacetyl indole into 1000ml methanol, slowly drop an appropriate amount of 50% KOH solution, heat up and reflux for 18 hours, cool to room temperature, The methanol was recovered by concentration, and the residual liquid was left; 1500 ml of water was added to the residual liquid, hydrochloric acid was added dropwise to adjust pH=3～4, and then filtered, and the solid obtained by filtration was dried to obtain 144g of indole-3-carboxylic acid crude product; The crude product was slurried with 100g of ethyl acetate for 25 minutes,filtered and dried to obtain indole-3-carboxylic acid (137g, yield 91.8%).
General Description
The structures of the derivatives of indole-3-carboxylic acid were studied using gas chromatography with high resolution mass spectrometry (GC-HRMS), ultra-high performance liquid chromatography in combination with high resolution tandem mass spectrometry (UHPLC-HRMS), nuclear magnetic resonance spectroscopy (NMR) and Fourier transform infrared spectroscopy (FT-IR).
