1912-35-2

Basic information

• Product Name: Methyl 2-(2-bromo-1H-indol-3-yl)acetate
• Synonyms: (2-Bromo-1H-indol-3-yl)-aceticacidmethylester;METHYL 2-(2-BROMO-1H-INDOL-3-YL)ACETATE
• CAS NO: 1912-35-2
• Molecular Formula: C₁₁H₁₀BrNO₂
• Molecular Weight: 268.11
• Mol File: 1912-35-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 394.1 °C at 760 mmHg
• Flash Point: 192.2 °C
• Appearance: /
• Density: 1.569 g/cm³
• Refractive Index: 1.648
• CAS DataBase Reference: Methyl 2-(2-bromo-1H-indol-3-yl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-(2-bromo-1H-indol-3-yl)acetate(1912-35-2)
• EPA Substance Registry System: Methyl 2-(2-bromo-1H-indol-3-yl)acetate(1912-35-2)

Safety Data

• Hazardous Substances Data: 1912-35-2(Hazardous Substances Data)

Usage

General Description

Methyl 2-(2-bromo-1H-indol-3-yl)acetate is a chemical compound with the molecular formula C11H10BrNO2. It is a derivative of indole, a heterocyclic organic compound. Methyl 2-(2-bromo-1H-indol-3-yl)acetate is commonly used in the synthesis of pharmaceutical and agrochemical products due to its potential biological activities. It is also utilized as an intermediate in the production of various organic compounds, including those used in the manufacture of dyes and fragrances. Methyl 2-(2-bromo-1H-indol-3-yl)acetate may also be used in academic research for the study of indole derivatives and their potential applications in medicinal chemistry.

InChI:InChI=1/C11H10BrNO2/c1-15-10(14)6-8-7-4-2-3-5-9(7)13-11(8)12/h2-5,13H,6H2,1H3

Upstream product

• 1912-33-0 Indole-3-acetic acid methyl ester 
• 771-51-7 indole-3-acetonitrile 
• 87-51-4 indole-3-acetic acid 

Downstream Products

• 1374335-75-7 C₂₆H₂₉BrN₂O₅ 
• 142273-18-5 paullone 
• 924627-44-1 [2-(2-aminophenyl)-1H-indol-3-yl]acetic acid methyl ester 
• 1609008-20-9 C₁₇H₁₄BrNO₄S 
• 1609008-21-0 C₂₂H₂₃NO₅S 
• 1609008-22-1 C₂₂H₂₁NO₄S 

Relevant articles and documents

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Depsipeptides Featuring a Neutral P1 Are Potent Inhibitors of Kallikrein-Related Peptidase 6 with On-Target Cellular Activity

Kallikrein-related peptidase 6 (KLK6) is a secreted serine protease that belongs to the family of tissue kallikreins (KLKs). Many KLKs are investigated as potential biomarkers for cancer as well as therapeutic drug targets for a number of pathologies. KLK6, in particular, has been implicated in neurodegenerative diseases and cancer, but target validation has been hampered by a lack of selective inhibitors. This work introduces a class of depsipeptidic KLK6 inhibitors, discovered via high-throughput screening, which were found to function as substrate mimics that transiently acylate the catalytic serine of KLK6. Detailed structure-activity relationship studies, aided by in silico modeling, uncovered strict structural requirements for potency, stability, and acyl-enzyme complex half-life. An optimized scaffold, DKFZ-251, demonstrated good selectivity for KLK6 compared to other KLKs, and on-target activity in a cellular assay. Moreover, DKFZ-633, an inhibitor-derived activity-based probe, could be used to pull down active endogenous KLK6.

Biomimetic total syntheses of borreverine and flinderole alkaloids

Dimeric indole alkaloids represent a structurally unique class of natural products having interesting biological activities. Recently, we reported the first total synthesis of flinderoles B and C, structurally unique and potent antimalarial natural products. Central to the design of the approach and by virtue of a one-pot, acid-catalyzed dimerization reaction, the route also provided total synthesis of the borreverine class of natural products. This full account details the progress of efforts that culminated in the protecting-group-free, six-step total synthesis of all of the flindersia alkaloids: dimethylisoborreverine, isoborreverine, flinderoles A-C, and their analogues. A biomimetic approach featuring a scalable and catalytic formal [3 + 2] cycloaddition and Diels-Alder reaction is outlined in detail. On the basis of the experimental observations, a detailed mechanism has been proposed for the dimerization of tertiary alcohol 28.