167479-13-2

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Bromoindole-2-carboxylic acid methyl ester is used as an intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique structure and reactivity contribute to the development of new drugs with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-Bromoindole-2-carboxylic acid methyl ester is utilized as a key component in the design and synthesis of novel compounds with potential biological activities. Its versatility allows for the exploration of various chemical modifications to enhance the pharmacological properties of the resulting compounds.
Used in Drug Discovery:
4-Bromoindole-2-carboxylic acid methyl ester plays a significant role in drug discovery, where it serves as a starting material for the development of new chemical entities. Its potential pharmacological properties and biological activities make it an attractive candidate for further research and development in the pharmaceutical industry.
Used in Organic Chemistry Research:
4-Bromoindole-2-carboxylic acid methyl ester is also used in organic chemistry research to study its reactivity and explore its potential applications in various chemical reactions. Its unique structure provides opportunities for the synthesis of new organic compounds and the investigation of novel reaction mechanisms.

Upstream product

• 16732-64-2 4-bromo-1H-indole-2-carboxylic acid 
• 74-88-4 methyl iodide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67-56-1 methanol 
• 52488-36-5 4-bromo-1H-indole 
• 558-13-4 carbon tetrabromide 
• 220448-44-2 C₁₀H₈BrN₃O₂ 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 1362861-01-5 methyl 4-(4-methoxyphenyl)-1H-indole-2-carboxylate 
• 1362861-28-6 11-(4-hydroxyphenyl)chromeno[3,4-b]indole-6(7H)-one 
• 1362861-29-7 2-hydroxy-11-(4-hydroxyphenyl)chromeno[3,4-b]indole-6(7H)-one 
• 1362861-03-7 methyl 3-iodo-4-(4-methoxyphenyl)-1H-indole-2-carboxylate 
• 1362861-10-6 methyl 3-(2-methoxyphenyl)-4-(4-methoxyphenyl)-1H-indole-2-carboxylate 
• 1362861-11-7 methyl 3-(2,5-dimethoxyphenyl)-4-(4-methoxyphenyl)-1H-indole-2-carboxylate 
• 1446308-69-5 C₁₆H₁₄BrNO₃S 
• 1446308-70-8 C₁₆H₁₃BrClNO₂S 

Relevant academic research and scientific papers

METHODS AND COMPOUNDS FOR RESTORING MUTANT p53 FUNCTION

Mutations in oncogenes and tumor suppressors contribute to the development and progression of cancer. The present disclosure describes compounds and methods to recover wild-type function to p53 mutants. The compounds of the present disclosure can bind to mutant p53 and restore the ability of the p53 mutant to bind DNA and activate downstream effectors involved in tumor suppression. The disclosed compounds can be used to reduce the progression of cancers that contain a p53 mutation.

TRANSGLUTAMINASE 2 (TG2) INHIBITORS

Described herein are compounds and pharmaceutical compositions containing such compounds which inhibit transglutaminase 2 (TG2). Also described herein are methods for using such TG2 inhibitors, alone or in combination with other compounds, for treating diseases or conditions that would benefit from TG2 inhibition.

A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger–Knittel Indole Synthesis

The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.

Visible-Light-Induced Direct Photocatalytic Carboxylation of Indoles with CBr4/MeOH

Photocatalysis enables the cascade reactions of indoles and CBr4 in MeOH through a C(sp2)-H functionalization/methanolysis sequence. The title reaction provides an efficient access to indole 2- and 3-carboxylates in a single operation (no preinstallation of protecting as well as directing groups was required) with good yields under mild reaction conditions. Shedding light on indole: The regioselective alkoxycarboxylation of indoles and heteroarenes using the CBr4/MeOH couple was accomplished through visible-light-induced photoredox catalysis. The described photocatalytic strategy features operational simplicity as well as high functional-group tolerance and represents a direct procedure to access indole carboxylates in generally moderate to good yields (see scheme).

Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: A novel DYRK1A inhibitor class

A library of substituted chromeno[3,4-b]indoles was developed as Lamellarin isosters. Synthesis was achieved from indoles after a four-step pathway sequence involving C-3 iodination, a Suzuki cross-coupling reaction, and a one pot deprotection/lactonisation step. Twenty final compounds were tested in order to determine their activity against topoisomerase I and kinases, the two major biological activities of Lamellarins. One newly synthesized derivative exhibited a strong topoisomerase activity comparable to reference compounds such as campthotecin and Lamellarin with only a weak kinase inhibition. Two other lead compounds were identified as new nanomolar DYRK1A inhibitors and several other drugs affected the kinases in the sub-micromolar range. These results will enable us to use the chromeno[3,4-b]indole as a pharmacophore to develop potent treatments for neurological or oncological disorders in which DYRK1A is fully involved.

Rapid and easy access to indoles via microwave-assisted Hemetsberger-Knittel synthesis

Hemetsberger-Knittel indole synthesis can be carried out under microwave activation. The optimum reaction conditions were found by using different solvents and by varying irradiation times and temperature. After 10 min of microwave irradiation, high conversion into the corresponding indole products was achieved without formation of any side products.

Novel quinolinequinone antitumor agents: Structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1)

A series of quinolinequinones bearing various substituents has been synthesized, and the effects of substituents on the metabolism of the quinones by recombinant human NAD(P)H:quinone oxidoreductase (hNQO1) was studied. A range of quinolinequinones were selected for study, and were specifically designed to probe the effects of aryl substituents at C-2. A range of 28 quinolinequinones 2-29 was prepared using three general strategies: the palladium(0) catalyzed coupling of 2-chloroquinolines, the classical Friedlaender synthesis and the double-Vilsmeier reaction of acetanilides. One example of an isoquinolinequinone 30 was also prepared, and the reduction potentials of the quinones were measured by cyclic voltammetry. For simple substituents R2 at the quinoline 2-position, the rates of quinone metabolism by hNQO1 decrease for R2=Cl>H～Me>Ph. For aromatic substituents, the rate of reduction decreases dramatically for R 2=Ph>1-naphthyl>2-naphthyl>4-biphenyl. Compounds containing a pyridine substituent are the best substrates, and the rates decrease as R 2=4-pyridyl>3-pyridyl>2-pyridyl>4-methyl-2-pyridyl>5- methyl-2-pyridyl. The toxicity toward human colon carcinoma cells with either no detectable activity (H596 or BE-WT) or high NQO1 activity (H460 or BE-NQ) was also studied in representative quinones. Quinones that are good substrates for hNQO1 are more toxic to the NQO1 containing or expressing cell lines (H460 and BE-NQ) than the NQO1 deficient cell lines (H596 and BE-WT).

4-Oxo-3,5-dihydro-4H-pyridazino[4,5-b]-indole-1-acetamide derivatives, their preparation and their application in therapy

Compounds of general formula (I) in which X represents a hydrogen or halogen atom or a methyl, methoxy or phenylmethoxy group, Y represents a hydrogen atom, 1 or 2 halogen atoms or a hydroxyl, methoxy, nitro or methyl group, R1represents a hydr