71086-99-2

Basic information

• Product Name: 5-AMINO-2-INDOLE CARBOXYLIC ACID
• Synonyms: 5-Aminoindole-2-carboxylic acid;1H-Indole-2-carboxylicacid,5-amino-,ethylester(9CI);5-AMINO-2-INDOLE CARBOXYLIC ACID ETHYL ESTER;5-Amino-2-indole carboxylic acid ,96%;Ethyl 5-AMinoindole-2-carboxylate;5-amino-1H-Indole-2-carboxylic acid ethyl ester
• CAS NO: 71086-99-2
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 176.17
• Product Categories: AMINOACID
• Mol File: 71086-99-2.mol
• Article Data: 51

Chemical Properties

• Melting Point: 126-127 °C
• Boiling Point: 420.097 °C at 760 mmHg
• Flash Point: 207.867 °C
• Appearance: /
• Density: 1.288 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: 2-8°C(protect from light)
• PKA: 15.41±0.30(Predicted)
• CAS DataBase Reference: 5-AMINO-2-INDOLE CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-2-INDOLE CARBOXYLIC ACID(71086-99-2)
• EPA Substance Registry System: 5-AMINO-2-INDOLE CARBOXYLIC ACID(71086-99-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 71086-99-2(Hazardous Substances Data)

Usage

General Description

5-AMINO-2-INDOLE CARBOXYLIC ACID is a chemical compound with the molecular formula C10H9N2O2. It is an indole derivative that contains an amino group and a carboxylic acid group. 5-AMINO-2-INDOLE CARBOXYLIC ACID is commonly used in the synthesis of pharmaceuticals and organic compounds. It has been investigated for its potential biological activities and has shown promise in various applications, including as a potential anticancer agent. The compound exhibits interesting properties due to its indole ring structure and has the potential for further exploration in drug development and medicinal chemistry.

InChI:InChI=1/C11H12N2O2/c1-2-15-11(14)10-6-7-5-8(12)3-4-9(7)13-10/h3-6,13H,2,12H2,1H3

Upstream product

• 63190-15-8 ethyl (Z)-2-(2-(4-nitrophenyl)hydrazineylidene)propanoate 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 73647-04-8 ethyl 2-[2-(4-nitrophenyl)hydrazinylidene]propanoate 
• 100-16-3 4-nitrophenylhydrazone 
• 1227862-58-9 5'-amino-4-phenyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-ol 
• 16732-57-3 5-nitro-indole-2-carboxylic acid ethyl ester 
• 138731-14-3 1H-indole-2,5-dicarboxylic acid 2-ethyl ester 
• 409315-76-0 5-isocyanato-indole-2-carboxylic acid ethyl ester 

Downstream Products

• 383674-95-1 ethyl 5-[[[(3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]amino]-1H-indole-2-carboxylate 
• 179556-52-6 1-benzyl-4-(N-methyl-N-(3-methoxymethyl-2-pyridinyl)amino)piperidine 
• 179556-27-5 (Z)-1-benzyl-4-(N-methyl-N-(3-(propen-1-yl)-2-pyridinyl)amino)piperidine 
• 179557-31-4 1-benzyl-4-[N-methyl-N-(3-(1-methylcyclopropylamino)-2-pyridinyl)amino]piperidine 

Relevant articles and documents

Synthesis of new gramine-type analogs of CC-1065

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Design, synthesis and biological evaluation of novel FXIa inhibitors with 2-phenyl-1H-imidazole-5-carboxamide moiety as P1 fragment

Factor XIa, as a blood coagulation enzyme, amplifies the generation of the last enzyme thrombin in the blood coagulation cascade. It was proved that direct inhibition of factor XIa could reduce pathologic thrombus formation without an enhanced risk of bleeding. WSJ-557, a nonpurine imidazole-based xanthine oxidase inhibitor in our previous reports, could delay blood coagulation during its animal experiments, which prompted us to investigate its action mechanism. Subsequently, during the exploration of the action mechanism, it was found that WSJ-557 exhibited weak in vitro factor XIa binding affinity. Under the guide of molecular modeling, we adopted molecular hybridization strategy to develop novel factor XIa inhibitors with WSJ-557 as an initial compound. This led to the identification of the most potent compound 44g with a Ki value of 0.009 μM, which was close to that of BMS-724296 (Ki = 0.0015 μM). Additionally, serine protease selectivity study indicated that compound 44g display a desired selectivity, more 400-fold than those of thrombin, factor VIIa and factor Xa in coagulation cascade. Moreover, enzyme kinetics studies suggested that the representative compound 44g acted as a competitive-type inhibitor for FXIa, and molecular modeling revealed that it could tightly bind to the S1, S1′ and S2′ pockets of factor XIa. Furthermore, in vivo efficacy in the rabbit arteriovenous shunt model suggested that compound 44g demonstrated dose-dependent antithrombotic efficacy. Therefore, these results supported that compound 44g could be a potential and efficacious agent for the treatment of thrombotic diseases.

Design, synthesis, and biological evaluation of 5-((8-methoxy-2-methylquinolin-4-yl)amino)-1H-indole-2-carbohydrazide derivatives as novel Nur77 modulators

Nur77 is a potential target for the treatment of cancer such as HCC. Herein, we detailed the discovery of a novel series of 5-((8-methoxy-2-methylquinolin-4-yl)amino)-1H-indole-2-carbohydrazide derivatives as potential Nur77 modulators. The studies of antiproliferative activity and Nur77-binding affinity of target compounds resulted in the discovery of a lead candidate (10g), which was a good Nur77 binder (KD = 3.58 ± 0.16 μM) with a broad-spectrum antiproliferative activity against all tested hepatoma cells (IC50 2.0 μM) and was low toxic to normal LO2 cells. 10g could up-regulate Nur77 expression and mediate sub-cellular localization of Nur77 to induce apoptosis in hepatocellular carcinoma cell lines, which relied on 10g inducing Nur77-dependent autophagy and endoplasmic reticulum stress as the upstream of apoptosis. Moreover, the in vivo assays verified that 10g significantly inhibited xenograft tumor growth. These results indicate that 10g has the potential to be developed as a novel Nur77-targeting anti-hepatoma drug.