106698-07-1

Usage

Uses

Used in Pharmaceutical Research:
1-Acetyl-5-bromoindolin-3-one is used as a research intermediate for the preparation of indole derivatives and analogs. Its application is primarily driven by its ability to contribute to the development of compounds with 5-HT6 receptor antagonistic activity, which can be crucial in the treatment of various neurological and psychiatric disorders.
Used in Drug Development:
In the pharmaceutical industry, 1-Acetyl-5-bromoindolin-3-one is utilized as a key component in the synthesis of novel drugs targeting the 5-HT6 receptor. This receptor is associated with cognitive functions, and its modulation has been linked to potential therapeutic benefits in conditions such as Alzheimer's disease, schizophrenia, and obesity. The compound's role in drug development is to facilitate the creation of new molecules with improved efficacy and selectivity for the 5-HT6 receptor.
Used in Chemical Synthesis:
1-Acetyl-5-bromoindolin-3-one is also employed in chemical synthesis as a versatile building block for the creation of various indole-based compounds. Its unique structure allows for further functionalization and modification, enabling the synthesis of a wide range of molecules with diverse biological activities and potential applications in different fields, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C10H8BrNO2/c1-6(13)12-5-10(14)8-4-7(11)2-3-9(8)12/h2-4H,5H2,1H3

Upstream product

• 106698-05-9 1-acetyl-5-bromo-3-hydroxy-2-methoxyindole 
• 33588-54-4 5-bromoindoxyl diacetate 
• 61995-52-6 1-(5-bromo-1H-indol-1-yl)ethan-1-one 
• 610-71-9 2,5-dibromobenzoic acid 
• 32253-75-1 5-bromo-2-<(carboxymethyl)amino>-benzoic acid 
• 17357-14-1 5-bromo-3-indoxyl acetate 
• 10075-50-0 5-bromo-1H-indole 
• 868694-19-3 5-bromo-3-iodo-1H-indole 

Downstream Products

• 1276688-15-3 (S)-1-acetyl-5-bromo-2-((S)-2-nitro-1-phenylethyl)indolin-3-one 

Relevant academic research and scientific papers

Synthesis and evaluation of analogues of 10H-indolo[3,2-b]-quinoline as G-quadruplex stabilising ligands and potential inhibitors of the enzyme telomerase

We report here the synthesis and evaluation for telomerase-inhibitory and quadruplex DNA binding properties of several rationally-designed quindoline analogues, substituted at the 2- and 7- positions. The ability of these compounds to interact with and stabilise an intramolecular G-quadruplex DNA against increases in temperature was evaluated by a fluorescence-based (FRET) melting assay. The resulting Tm values were found to correlate with their potency for telomerase inhibition, as measured in an in vitro telomerase TRAP assay. The interactions of a number of compounds with a quadruplex DNA molecular structure were simulated by molecular modelling methods. It is concluded that this class of compound represents a new chemical type suitable for further development as telomerase inhibitors.

Indoxyl-based umpolung strategy for the synthesis of unsymmetrical 3,3′-biindoles

3,3′-Bisindoles are known to be important structural motifs found in bioactive natural products, pharmaceuticals, and functional materials. Herein, a novel indoxyl-based approach was established for the synthesis of unsymmetrical 3,3′-biindoles from indoles and indoxyls. This approach generated moderate to excellent yields of the desired products (24 examples, up to 98% yield). The present method features broad substrate scope, operational simplicity, high atom economy, and utilization of non-toxic and inexpensive molecular iodine as catalyst. The applicability of this method has been demonstrated by the facile gram-scale synthesis.

Araf51 with improved transglycosylation activities: One engineered biocatalyst for one specific acceptor

A random mutagenesis of the arabinofuranosyl hydrolase Araf51 has been run in order to have access to efficient biocatalysts for the synthesis of alkyl arabinofuranosides. The mutants were selected on their ability to catalyze the transglycosylation reaction of p-nitrophenyl α-l-arabinofuranoside (pNP-Araf) used as a donor and various aliphatic alcohols as acceptors. This screening strategy underlined 5 interesting clones, each one corresponding to one acceptor. They appeared to be much more efficient in the transglycosylation reaction compared to the wild type enzyme whereas no self-condensation or hydrolysis products could be detected. Moreover, the high specificity of the mutants toward the alcohols for which they have been selected validates the screening process. Sequence analysis of the mutated enzymes revealed that, despite their location far from the active site, the mutations affect significantly the kinetics properties as well as the substrate affinity of these mutants toward the alcohol acceptors in the transglycosylation reaction.

Indole-3-piperazinyl derivatives: Novel chemical class of 5-HT6 receptor antagonists

N1-Arylsulfonyl-3-piperazinyl indole derivatives were designed and identified as a novel class of 5-HT6 receptors ligands. All the compounds have high affinity and antagonist activity towards 5-HT6 receptor. The compound 7a (Ki = 3.4 nM, functional assay IC 50 = 310 nM) shows enhanced cognitive effect when tested in NORT and Morris water maze models. Synthesis, SAR and PK profile of these novel compounds constitute the subject matter of this Letter.

Derivatives of Thiourea and Thiosemicarbazide. Structure, Transformations, and Pharmacological Activity. V. Imidazo[4,5-b]indoles

Bromination of 1-acetyl-3-indolinone and its 5-bromoderivative followed by the reaction of the formed 2-bromoderivatives of indolinone with ammonia and amines result in the formation of 2-amino-1-acetyl-3-indolinones which by the reaction with potassium r

A convenient synthesis of 1,2-dihydro-3H-indol-3-ones and 1,2-dihydro-2H-indol-2-ones by Baeyer-Villiger oxidation

The Baeyer-Villiger rearrangement of substituted 1H-indole-3-carbaldehydes afforded the corresponding substituted 1,2-dihydro-3H-indol-3-ones. The influence of 3-carbonyl and 1-protecting groups has been examined. Reaction has been extended to 1H-indole-2-carbaldehydes and used for synthesis of 1-(phenylsulfonyl)-1H-indol-2-yl trifluoromethanesulfonate.

A Novel Synthesis of 1-Acylindoxyls

A novel and efficient synthesis of 1-acylindoxyls (3) from 1-acylindoles (1) is described.The procedure involves the demethoxylation with stannic chloride of 1-acyl-3-hydroxy-2-methoxy-indoline (2), which were obtained by the MoO5 oxidation of 1 in methanol.Since the MoO5 oxidation of 2-substituted 1-acylindoles (1f and 1g) gave not the corresponding indolines (2f and 2g), but 2-hydroxyindoxyls (4f and 4g), 2f and 2g were obtained by the methylation of 4f and 4g with diazomethane to give 5f and 5g, followed by the reduction of 5f and 5g with sodium borohydride, respectively.Keywords - indoxyl; indole; indoline; oxidation; demethoxylation; peroxomolybdenum complex; methylation; diazomethane; reduction; sodium borohydride