32387-21-6 Usage
Description
1-Methyl-1H-indole-3-carboxylic acid is an indole derivative, characterized as an off-white solid. It is synthesized through the oxidation of 1-methylindole-3-aldehyde using alkaline potassium permanganate. 1-Methyl-1H-indole-3-carboxylic acid serves as a versatile reactant in the pharmaceutical and chemical industries for the preparation of various bioactive molecules.
Uses
Used in Pharmaceutical Industry:
1-Methyl-1H-indole-3-carboxylic acid is used as a reactant for the preparation of bisindolyl pyrimidinones, which are analogs of the PKC inhibitor LY333531. These compounds play a role in regulating protein kinase C, a crucial enzyme involved in various cellular signaling pathways.
1-Methyl-1H-indole-3-carboxylic acid is also used as a reactant for the preparation of (heteroaryl)(carboxamido)arylpyrrole derivatives. These derivatives act as Cdc7 kinase inhibitors, exhibiting antitumor and antiproliferative properties, making them valuable in cancer research and treatment.
In the field of immunology, 1-Methyl-1H-indole-3-carboxylic acid is utilized as a reactant for the synthesis of (pyrrolidinylmethoxy)cyclohexanecarboxylic acids. These compounds serve as antigen-4 (VLA-4) antagonists, which can potentially modulate immune responses and be applied in the treatment of autoimmune diseases.
Furthermore, this compound is used as a reactant for the preparation of EphB3 receptor tyrosine kinase inhibitors. These inhibitors target the EphB3 receptor, which is involved in cell signaling and has been implicated in various diseases, including cancer.
1-Methyl-1H-indole-3-carboxylic acid is also employed in the synthesis of pyrazolodiazepine derivatives, which act as human P2X7 receptor antagonists. These antagonists can potentially be used in the treatment of inflammatory and neurodegenerative diseases.
Additionally, this compound is used as a reactant for the preparation of potent nonpeptidic urotensin II receptor agonists. These agonists can be applied in the study and treatment of various cardiovascular and renal diseases.
Lastly, 1-Methyl-1H-indole-3-carboxylic acid is used in the synthesis of pyrrolizidine esters, amides, and ureas, which serve as 5-HT4 receptor ligands. These ligands can be utilized in the development of drugs targeting the serotonin system, with potential applications in the treatment of gastrointestinal, cardiovascular, and central nervous system disorders.
Check Digit Verification of cas no
The CAS Registry Mumber 32387-21-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,2,3,8 and 7 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 32387-21:
(7*3)+(6*2)+(5*3)+(4*8)+(3*7)+(2*2)+(1*1)=106
106 % 10 = 6
So 32387-21-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H9NO2/c1-11-6-8(10(12)13)7-4-2-3-5-9(7)11/h2-6H,1H3,(H,12,13)
32387-21-6Relevant articles and documents
Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles
Nemoto, Koji,Tanaka, Shinya,Konno, Megumi,Onozawa, Satoru,Chiba, Masafumi,Tanaka, Yuuki,Sasaki, Yosuke,Okubo, Ryo,Hattori, Tetsutaro
, p. 734 - 745 (2016/01/15)
Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.
Copper-catalyzed methyl esterification reactions via C-C bond cleavage
Zhu, Yan,Yan, Hong,Lu, Linhua,Liu, Defu,Rong, Guangwei,Mao, Jincheng
, p. 9898 - 9905 (2013/10/22)
The highly effective synthesis of methyl esters from benzylic alcohols, aldehydes, or acids via copper-catalyzed C-C cleavage from tert-butyl hydroperoxide is reported in this paper for the first time. Our protocol is easily accessible and practical, making it a possible supplement for the traditional way.
