87802-11-7

Basic information

• Product Name: 5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 5-CHLOROINDOLE-2-CARBOXYLIC ACID METHYL ESTER;5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER;AKOS JY2082797;METHYL 5-CHLOROINDOLE-2-CARBOXYLATE;Methyl 5-chloro-1H-indole-2-carboxylate;1H-Indole-2-carboxylic acid, 5-chloro-, Methyl ester
• CAS NO: 87802-11-7
• Molecular Formula: C₁₀H₈ClNO₂
• Molecular Weight: 209.63
• Mol File: 87802-11-7.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 365.5 °C at 760 mmHg
• Flash Point: 174.8 °C
• Appearance: /
• Density: 1.381 g/cm³
• Vapor Pressure: 1.56E-05mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER(87802-11-7)
• EPA Substance Registry System: 5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER(87802-11-7)

Safety Data

• Hazardous Substances Data: 87802-11-7(Hazardous Substances Data)

Usage

General Description

5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER is a chemical compound with the molecular formula C10H8ClNO2. It is a methyl ester derivative of 5-chloro-1H-indole-2-carboxylic acid, and it is commonly used in organic synthesis and pharmaceutical research. 5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER has potential applications in the development of new drugs and medications due to its biological activity and pharmacological properties. It is an important intermediate in the synthesis of various pharmaceutical compounds and can be used as a building block in the production of other organic compounds. Additionally, 5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER may also have other industrial applications in the manufacturing of chemicals and materials.

InChI:InChI=1/C10H8ClNO2/c1-14-10(13)9-5-6-4-7(11)2-3-8(6)12-9/h2-5,12H,1H3

Upstream product

• 63069-48-7 p-chloro-o-iodoaniline 
• 55477-80-0 methyl 2-[(tert-butoxycarbonyl)amino]acrylate 
• 10517-21-2 5-chloro-1H-Indole-2-carboxylic acid 
• 380374-20-9 C₁₀H₁₀ClNO₂ 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 956903-52-9 C₁₀H₁₁ClN₂O₂ 
• 174265-12-4 2-bromo-5-chlorobenzaldehyde 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 944275-74-5 C₁₀H₈ClN₃O₂ 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1072943-49-7 4-chloro-2-(2,2-dibromoethenyl)benzenamine 
• 131770-31-5 N-(4-Chlorophenyl)glycine methyl ester 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 1609930-26-8 ethyl 5-chloro-3-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)-1H-indol-2-ylcarbamate 
• 1609930-27-9 ethyl 5-chloro-3-(1-(3,5-dimethylphenyl)-2,2,2-trifluoro-1-hydroxyethyl)-1H-indol-2-ylcarbamate 
• 540740-53-2 methyl 5-chloro-3-[(3-methylphenyl)thio]-1H-indole-2-carboxylate 

Relevant articles and documents

Design, synthesis, biological evaluation and docking study of novel indole-2-amide as anti-inflammatory agents with dual inhibition of COX and 5-LOX

In this work, a series of novel indole-2-amide compounds were designed, synthesized, characterized and the anti-inflammatory activity in vivo were evaluated. Compounds 8a, 10b, 12h, and 12l exhibited marked anti-inflammatory activity in 2,4-Dinitrofluorob

Novel indole hydrazide derivatives: Synthesis and their antiproliferative activities through inducing apoptosis and DNA damage

A series of novel indole hydrazide derivatives was synthesized and evaluated for their anticancer activities. Compound 12 exhibited the highest antiproliferative activity against the MCF-7 cell line, with an IC50 value of 3.01 μM. Treatment of MCF-7 cells with compound 12 led to cell cycle arrest at the G0/G1 phase and also displayed a significant annexin V binding pattern, indicating that compound 12 is effective in apoptotic cell death. The Western blot analysis showed that compound 12 increased the expression of proapoptotic Bax and decreased the levels of the antiapoptotic Bcl-2 protein. It was also observed that MCF-7 cells treated with compound 12 showed reduced levels of procaspase-3 and -9 proteins. Moreover, compound 12 treatment induced a significant DNA damage in MCF-7 cells by increasing H2AX and ATM phosphorylation.

Intracellular Trapping of the Selective Phosphoglycerate Dehydrogenase (PHGDH) Inhibitor BI-4924 Disrupts Serine Biosynthesis

Phosphoglycerate dehydrogenase (PHGDH) is known to be the rate-limiting enzyme in the serine synthesis pathway in humans. It converts glycolysis-derived 3-phosphoglycerate to 3-phosphopyruvate in a co-factor-dependent oxidation reaction. Herein, we report the discovery of BI-4916, a prodrug of the co-factor nicotinamide adenine dinucleotide (NADH/NAD+)-competitive PHGDH inhibitor BI-4924, which has shown high selectivity against the majority of other dehydrogenase targets. Starting with a fragment-based screening, a subsequent hit optimization using structure-based drug design was conducted to deliver a single-digit nanomolar lead series and to improve potency by 6 orders of magnitude. To this end, an intracellular ester cleavage mechanism of the ester prodrug was utilized to achieve intracellular enrichment of the actual carboxylic acid based drug and thus overcome high cytosolic levels of the competitive cofactors NADH/NAD+