53590-48-0

Usage

Chemical Properties

Off-white solid

InChI:InChI=1/C9H8BrNO/c10-7-1-2-9-6(3-7)4-8(5-12)11-9/h1-4,11-12H,5H2

Upstream product

• 16732-70-0 ethyl 5-bromoindolecarboxylate 
• 210345-56-5 5-bromo-1H-indole-2-carboxylic acid methyl ester 
• 7254-19-5 5-bromo-2-indolecarboxylic acid 

Downstream Products

• 53590-50-4 5-bromo-1H-indole-2-carbaldehyde 

Relevant academic research and scientific papers

Amide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility

Indolecarboxamides are potent but poorly soluble mycobactericidal agents. Here we found that modifying the incipient scaffold by amide-amine substitution and replacing the indole ring with benzothiophene or benzoselenophene led to striking (10-20-fold) im

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones

The aromatic nitrogen atoms of heteroarylaldehydes are activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products are afforded in good to excellent yields and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichemicals for plant protection.

SPIROCHROMANE DERIVATIVES

The invention relates to spirochromane derivatives, or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof, as well as to pharmaceutical compositions containin

PROTEIN KINASE C AGONISTS

The present disclosure relates generally to certain diacylglycerol lactone compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions dis

IMIDAZO-PYRIDINE COMPOUNDS AS PAD INHIBITORS

Heterocyclic compounds of Formula (I), (II), and (III) are described herein along with their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof. The compounds described herein, their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosis, cutaneous lupus erythematosis, ulcerative colitis, cancer, cystic fibrosis, asthma, multiple sclerosis and psoriasis. The process of preparation of the compounds of Formula (I), (II), and (III), their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof, along with a pharmaceutical composition comprising a compound of Formula (I), Formula (II), Formula (III), or a pharmaceutically acceptable salt thereof have also been described.

Addition of a Carbene Catalyst to Indole Aryl Aldehyde Activates a Remote δ-sp2 Carbon for Protonation and Formal [4+2] Reaction

The addition of a carbene catalyst to an indole aryl aldehyde leads to the activation of a remote sp2 carbon that is five atoms away from the catalyst. The unsaturated Breslow intermediate formed between the catalyst and substrate undergoes an internal redox reaction and remote carbon protonation to generate an analogous azolium vinyl enolate intermediate. Subsequent [4+2] reaction with cyclic imine substrates eventually affords multicyclic pyridoindoles as nearly single diastereomers with excellent enantioselectivities.

Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.

THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION

Disclosed herein are compounds of formula (I), or a salt thereof and compositions comprising compounds of formula I that exhibit antibacterial activities, when tested alone and/or in combination with a bacterial efflux pump inhibitor. Also disclosed are methods of treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I alone or in combination with the administration of a bacterial efflux pump inhibitor.

Fluorination-Oxidation of 2-Hydroxymethylindole Using Selectfluor

An unexpected fluorination-oxidation of 2-hydroxymethylindole using selectfluor under mild condi-tions without a catalyst is described. This new chemistry allows for efficient and rapid synthesis of various 3-fluoroindole-2-aldehydes and novel quaternary

Facile Synthesis of 3-Halobenzo-heterocyclic-2-carbonyl Compounds via in situ Halogenation-Oxidation

A facile method to synthesize 3-halobenzo-heterocyclic-2-carbonyl compounds is described. Mechanistic studies suggested that a halo-cyclization process, which generated the unstable spiro-acetal transition state and readily convertible to the corresponding carbonyl compound might be involved. Diverse 3-halobenzo-heterocyclic-2-carbonyl compounds could be synthesized with up to 95 % yield in mild conditions with inexpensive starting materials. (Figure presented.).