1912-35-2

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
Methyl 2-(2-bromo-1H-indol-3-yl)acetate is used as a key intermediate in the synthesis of pharmaceutical and agrochemical products. Its unique structure and properties make it a valuable building block for the development of new drugs and agrochemicals with improved efficacy and selectivity.
Used in Organic Compounds Production:
Methyl 2-(2-bromo-1H-indol-3-yl)acetate is utilized as an intermediate in the production of various organic compounds, including those used in the manufacture of dyes and fragrances. Its presence in these compounds contributes to their color, stability, and sensory properties.
Used in Academic Research:
Methyl 2-(2-bromo-1H-indol-3-yl)acetate is employed in academic research for the study of indole derivatives and their potential applications in medicinal chemistry. Researchers explore its chemical properties, reactivity, and interactions with biological targets to gain insights into the development of novel therapeutic agents and agrochemicals.

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 academic research and scientific papers

Efficient Synthesis of the Peptide Fragment of the Natural Depsipeptides Jaspamide and Chondramide

A new method for the synthesis of the tripeptide part of the jaspamide and chondramide alkaloids using a Ugi reaction was developed. The reported approach is considerably shorter than all literature syntheses of the peptide parts of these natural products. A family of peptides with different substituents at the 2-position of the indole moiety was prepared to open up access to analogues of these natural products.

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.

Remarkable switch of regioselectivity in diels-alder reaction: Divergent total synthesis of borreverine, caulindoles, and flinderoles

Switchable reaction patterns of dimerization of indole substituted butadienes via a Lewis acid and thermal activation are reported. While under acidic conditions dimerization occurred around the internal double bond of the dienophile, a complete switch of

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.

New synthetic approach to paullones and characterization of their SIRT1 inhibitory activity

A series of 7,12-dihydroindolo[3,2-d][1]benzazepine-6(5H)-ones (paullones) substituted at C9/C10 (Br) and C2 (Me, CF3, CO2Me) have been synthesized by a one-pot Suzuki-Miyaura cross-coupling of an o-aminoarylboronic acid and methyl 2-iodoindoleacetate followed by intramolecular amide formation. Other approaches to the paullone scaffold based on Pd-catalyzed C-H activation were unsuccessful. In vitro enzymatic assay with recombinant human SIRT-1 indicated a strong inhibitory profile for the series, in particular the analogue with a methoxycarbonyl group at C2 and a bromine at C9. These compounds are, in general, inducers of granulocyte differentiation of the U937 acute leukemia cell line and cause a marked increase in pre-G1 of the cell cycle.

Synthesis of paullone and kenpaullone derivatives by photocyclization of 2-(2-chloro-1H-indol-3-yl)-N-arylacetamides

An efficient synthesis of paullone and kenpaullone derivatives in moderate to high yields has been achieved through photocyclizations of (2-chloro-1H-indole-3-yl)-N-arylacetamides in acetone at room temperature. Paullone and kenpaullone have been obtained

A remarkable ring contraction en route to the chartelline alkaloids

Weinheim (Chemical Equation Presented) One-of-a-kind. A bromine-induced rearrangement has been designed for the formation of the spiro-β-lactam ring present in the structurally unique chartelline alkaloids (see picture of chartelline A). This method is used in combination with others to provide rapid access to the carbocyclic skeletons of the chartelline, securine, and securamine alkaloids.