25888-01-1

Basic information

• Product Name: 5-HYDROXY-1,2-DIMETHYL-1H-INDOLE-3-CARBOXYLIC ACID
• Synonyms: 5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid(SALTDATA: FREE)
• CAS NO: 25888-01-1
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.22
• Mol File: 25888-01-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 465.7°C at 760 mmHg
• Flash Point: 235.5°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 1.79E-09mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: 5-HYDROXY-1,2-DIMETHYL-1H-INDOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXY-1,2-DIMETHYL-1H-INDOLE-3-CARBOXYLIC ACID(25888-01-1)
• EPA Substance Registry System: 5-HYDROXY-1,2-DIMETHYL-1H-INDOLE-3-CARBOXYLIC ACID(25888-01-1)

Safety Data

• Hazardous Substances Data: 25888-01-1(Hazardous Substances Data)

Usage

General Description

5-HYDROXY-1,2-DIMETHYL-1H-INDOLE-3-CARBOXYLIC ACID is a chemical compound that belongs to the indole carboxylic acid family. It is a derivative of the amino acid tryptophan and is involved in various metabolic and regulatory processes in the body. It has been studied for its potential role in neurotransmitter regulation, immune function, and as a precursor for the synthesis of important biomolecules. 5-HYDROXY-1,2-DIMETHYL-1H-INDOLE-3-CARBOXYLIC ACID has also been investigated for its potential therapeutic applications in the treatment of various diseases and disorders, including mood disorders, inflammation, and cancer. Its unique structure and biological activities make it a subject of ongoing research and interest in the fields of pharmacology and medicine.

InChI:InChI=1/C11H11NO3/c1-6-10(11(14)15)8-5-7(13)3-4-9(8)12(6)2/h3-5,13H,1-2H3,(H,14,15)

Upstream product

• 73975-59-4 methyl 5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylate 
• 870-85-9 ethyl 3-methylaminocrotonate 
• 15574-49-9 mecarbinate 
• 21759-70-6 ethyl (Z)-3-(methylamino)-2-butenoate 

Relevant articles and documents

Synthesis and biological evaluation of indole-3-carboxamide derivatives as antioxidant agents

Oxidative stress results in various pathologies and as consequence antioxidant agents have attracted uninterrupted attention. In this paper, a novel series of indole-3-carboxamide derivatives (6a–6l) were designed and synthesized based on the melatonin structure as novel antioxidants. All of them were evaluated for the antioxidant activities in vitro against human neuroblastoma SH-SY5Y cell line using H2O2 radical scavenging assay. The target compounds 6a, 6f and 6i indicated better activities than the positive control, ascorbic acid, and 6a exhibited the best antioxidant activity. In addition, the structure-activity relationships of the target compounds were also preliminarily summarized based on the obtained experimental data.

Design, synthesis and biological evaluation of a novel series of indole-3-carboxamide derivatives for cancer treatment as EGFR inhibitors

Background: As reported EGFR is a sialoglycoprotein with tyrosine kinase activity involved in control of cellular survival, multiplication, differentiation and metastasis. Dysregulation or aberrant expression of EGFR has been implicated in cell transformation and having oncogenic roles in a number of human cancers. Therefore EGFR has become a significant target for developing targeted therapy for cancer. Methods: A novel series of indole-3-carboxamide derivatives as EGFR inhibitors were designed, synthesized and evaluated for the anticancer activity in vitro against three EGFR high-expressed cancer cell lines (A549, HeLa, and SW480), one EGFR low-expressed cell line (HepG2) and one human liver normal cell line (HL7702) by MTT assay. Results: The target compounds 6c, 6f, 6i, 6j, 6l, 6r, 6u and 6x exhibited potent anticancer activities against the three tested cancer cell lines and weak cytotoxic effects on HepG2, which imply that the target compounds are probably effective in inhibiting EGFR. And they also did not show measurable activities in HL7702, which imply the target compounds are likely to overcome the nonspecific toxicity against normal cells. Particularly, the target compound 6x indicated equal to the positive control erlotinib. In addition, molecular docking studies demonstrated the target compound 6x may be the potential inhibitor to EGFR. Conclusion: A new EGFR inhibitor scaffold and a preliminary discussion on their SARs provide promising opportunities to guide further research on indole-3-carboxamide derivatives as novel anticancer agents.

N-H insertion reactions of rhodium carbenoids. Part 3. The development of a modified Bischler indole synthesis and a new protecting-group strategy for indoles

A modified version of the Bischler indole synthesis has been developed in which the key step is the N-H insertion reaction of rhodium carbene intermediates derived from α-diazo-β-ketoesters with anilines. Thus N-methylanilines 1 react with diazoketoesters 2 in the presence of dirhodium(II) acetate to give (N-arylamino)ketones 3, cyclisation of which using boron trifluoride-ethyl acetate or acidic ion exchange resin gives the indoles 4. In order to extend this method to the synthesis of N-unsubstituted indoles, a new protecting group strategy for indoles was developed. In this, anilines are reacted with α,β-unsaturated-esters or -sulfones to give the conjugate addition products 6 and 9, cyclisation of which gives indoles 8 and 11. The N-(2-ethoxycarbonylethyl)- and -(2-sulfonylethyl)- protecting groups are readily removed from indoles 8 and 11 by treatment with base.