2124-55-2 Usage
Description
Indole-4-carboxylic acid is an organic compound with the chemical formula C9H7NO2, featuring a beige powder appearance. It serves as a crucial intermediate in the synthesis of various biologically active molecules and pharmaceuticals.
Uses
Indole-4-carboxylic acid is used as a reactant for the preparation of a wide range of compounds with diverse applications across different industries. Here are some of its uses:
Used in Pharmaceutical Industry:
Indole-4-carboxylic acid is used as a reactant for the preparation of substituted indole derivatives, which act as histamine H3 antagonists. These antagonists are essential in the treatment of various conditions, including allergies and cognitive disorders.
Indole-4-carboxylic acid is also used as a reactant for the preparation of potent and selective inhibitors of human reticulocyte 15-lipoxygenase-1. These inhibitors play a significant role in the management of inflammatory diseases and cancer.
In the field of cancer research, Indole-4-carboxylic acid is used as a reactant for the preparation of inhibitors of Gli1-mediated transcription in the Hedgehog pathway. These inhibitors are crucial in the development of targeted cancer therapies.
Furthermore, Indole-4-carboxylic acid is used as a reactant for the preparation of pyridinyl carboxylates, which act as SARS-CoV 3CL proinhibitors. These inhibitors are vital in the development of antiviral drugs to combat SARS-CoV and other related coronaviruses.
Indole-4-carboxylic acid is also utilized as a reactant for the preparation of substituted bipiperidinylmethyl amides, which serve as CCR3 membrane binding ligands. These ligands are essential in the treatment of various immune disorders and allergies.
In addition, Indole-4-carboxylic acid is used as a reactant for the preparation of indole amide hydroxamic acids, which are potent inhibitors of histone deacetylases. These inhibitors play a crucial role in the regulation of gene expression and have potential applications in the treatment of various diseases, including cancer.
Lastly, Indole-4-carboxylic acid is used as a reactant for the preparation of 2-[[[4′-chloro-[1,1-biphenyl]-4-yl]thio]methyl]-N-hydroxybutanamide derivatives, which are specific metalloproteinase inhibitors. These inhibitors have potential applications in the treatment of various diseases, including neurodegenerative disorders and cancer.
Check Digit Verification of cas no
The CAS Registry Mumber 2124-55-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,2 and 4 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 2124-55:
(6*2)+(5*1)+(4*2)+(3*4)+(2*5)+(1*5)=52
52 % 10 = 2
So 2124-55-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H7NO2/c11-9(12)7-2-1-3-8-6(7)4-5-10-8/h1-5,10H,(H,11,12)/p-1
2124-55-2Relevant articles and documents
Indole- and benzothiophene-based histamine H3 antagonists
Santillan Jr., Alejandro,McClure, Kelly J.,Allison, Brett D.,Lord, Brian,Boggs, Jamin D.,Morton, Kirsten L.,Everson, Anita M.,Nepomuceno, Diane,Letavic, Michael A.,Lee-Dutra, Alice,Lovenberg, Timothy W.,Carruthers, Nicholas I.,Grice, Cheryl A.
, p. 6226 - 6230 (2010)
Previous research on histamine H3 antagonists has led to the development of a pharmacophore model consisting of a central phenyl core flanked by two alkylamine groups. Recent investigation of the replacement of the central phenyl core with heteroaromatic fragments resulted in the preparation of novel 3,5-, 3,6- and 3,7-substituted indole and 3,5-substituted benzothiophene analogs that demonstrate good to excellent hH3 affinities. Select analogs were profiled in a rat pharmacokinetic model.
Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D2 Receptor Through Fragmentation of a Bitopic Ligand
Mistry, Shailesh N.,Shonberg, Jeremy,Draper-Joyce, Christopher J.,Klein Herenbrink, Carmen,Michino, Mayako,Shi, Lei,Christopoulos, Arthur,Capuano, Ben,Scammells, Peter J.,Lane, J. Robert
, p. 6819 - 6843 (2015/09/22)
Recently, we have demonstrated that N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide (SB269652) (1) adopts a bitopic pose at one protomer of a dopamine D2 receptor (D2R) dimer to negatively modulate the binding of dopamine at the other protomer. The 1H-indole-2-carboxamide moiety of 1 extends into a secondary pocket between the extracellular ends of TM2 and TM7 within the D2R protomer. To target this putative allosteric site, we generated and characterized fragments that include and extend from the 1H-indole-2-carboxamide moiety of 1. N-Isopropyl-1H-indole-2-carboxamide (3) displayed allosteric pharmacology and sensitivity to mutations of the same residues at the top of TM2 as was observed for 1. Using 3 as an "allosteric lead", we designed and synthesized an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D2R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.
