Description
Indole-3-carboxylic acid is a plant metabolite derived from tryptophan that has been found in Arabidopsis and has diverse biological activities.1,2,3,4 It induces resistance in Arabidopsis against the plant necrotrophic fungus P. cucumerina when applied as a soil-drenching solution at a concentration of 150 µM prior to infection.2 Indole-3-carboxylic acid is cytotoxic to A549 human lung and MCF-7 human breast cancer cells (EC50s = 4.6 and 12.9 µg/ml, respectively) and inhibits HIV replication in infected H9 lymphocytes (IC50 = 16.4 µg/ml).3 Indole-3-carboxylic acid has also been used as a precursor in the synthesis of substituted thiadiazoles with anticancer activity.4WARNING This product is not for human or veterinary use.
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).
