184151-47-1

Usage

Uses

Used in Organic Synthesis:
Ethanone, 1-(6-chloro-1H-indol-3-yl)is utilized as a key intermediate in organic synthesis for the production of a variety of chemical compounds. Its presence in the synthesis process allows for the creation of molecules with diverse functional groups and properties, which can be tailored for specific applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, Ethanone, 1-(6-chloro-1H-indol-3-yl)is employed as a building block for the development of new drugs. Its unique structure contributes to the design of molecules with potential therapeutic effects, making it a valuable asset in drug discovery and medicinal chemistry.
Used in the Development of New Compounds:
Ethanone, 1-(6-chloro-1H-indol-3-yl)is also used in the creation of new compounds for various applications in the chemical industry. Its versatility and reactivity enable the synthesis of a wide range of products, from specialty chemicals to advanced materials.
Used in the Medical Industry:
Ethanone, 1-(6-chloro-1H-indol-3-yl)plays a significant role in the medical industry, where it is used in the development of novel therapeutic agents. Its incorporation into drug molecules can lead to the discovery of new treatments for various diseases and conditions, enhancing patient care and improving health outcomes.

Upstream product

• 17422-33-2 6-chloroindole 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 947589-64-2 3-acetyl-1-(2,6-difluorobenzyl)-6-chloro-1H-indole 

Relevant academic research and scientific papers

Weak Coordination-Guided Regioselective Direct Redox-Neutral C4 Allylation of Indoles with Morita-Baylis-Hillman Adducts

A weak carbonyl coordination-guided regioselective C4 allylation of indoles is demonstrated using the versatile Morita-Baylis-Hillman adduct in the presence of Rh catalysts in a redox-neutral fashion. The substrate scope, functional group diversity, oxidant free character, mechanistic aspects, and synthetic utilities are important practical features.

Palladium-catalyzed regioselective C-H fluoroalkylation of indoles at the C4-position

An exclusive catalytic C4-selective fluoroalkylation of indoles with highly active (1H, 1H-perfluoroalkyl)mesityliodonium triflate has been described. The key to its high regioselectivity is the appropriate choice of an easily accessible, cheap and removable directing group at the C3 position in the presence of a Pd(OAc)2 catalyst. Besides indole fluoroalkylation, the application of this strategy in other heteroarenes such as benzo[b]thiophene is also described.

Synthetic analogues of the marine bisindole deoxytopsentin: Potent selective inhibitors of MRSA pyruvate kinase

As part of an ongoing study to elucidate the SAR of bisindole alkaloid inhibitors against the evolutionary conserved MRSA pyruvate kinase (PK), we present here the synthesis and biological activity of six dihalogenated analogues of the naturally occurring sponge metabolite deoxytopsentin, including the naturally occurring dibromodeoxytopsentin. The most active compounds displayed potent low nanomolar inhibitory activity against MRSA PK with concomitant significant selectivity for MRSA PK over human PK orthologues. Computational studies suggest that these potent MRSA PK inhibitors occupy a region of the small interface of the enzyme tetramer where amino acid sequence divergence from common human PK orthologues may contribute to the observed selectivity.

A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study

Novel and efficient Mn(OAc)3?2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.

Rh(III)-Catalyzed [5 + 1] Annulation of Indole-enaminones with Diazo Compounds to Form Highly Functionalized Carbazoles

A novel Rh(III)-catalyzed C-H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic is that this transformation could smoothly furnish a novel [5 + 1] cyclization product with good to excellent yields (up to 95%), accompanied by the thorough removal of acetyl and N,N-dimethyl groups of two substrates from the target products, rather than the normally expected [4 + 2] cyclization products.

Cascade Reaction to Selectively Synthesize Multifunctional Indole Derivatives by IrIII-Catalyzed C?H Activation

An effective and condition-controlled way to synthesize with high selectivity a variety of functionalized indoles with potent biological properties has been developed. Notably, 2,4-dialkynyl indole products were obtained by direct double C?H bond alkynylation, whereas alkynyl at the C4 position could convert to carbonyl to generate 2-alkynyl-3,4-diacetyl indoles fast and effectively. Additionally, a one-pot relay catalytic reaction led to 2,5-di-alkynyl-3,4-diacetyl indoles when using a carbonyl group as the directing group and by controlling the type and quantity of additives. A possible mechanism was proposed based on many studies including deuterium-exchange experiments, the necessary conditions of product conversion, and the effect of water on the reaction.

Ketone-Directed Cobalt(III)-Catalyzed Regioselective C2 Amidation of Indoles

An efficient cobalt(III)-catalyzed method for the direct C-H amidation of unprotected indoles for 2-amino indole scaffold construction has been developed. With dioxazolone as the amidating reagent, a variety of 2-amino indole derivatives were achieved in moderate to excellent yields using an organic acid as the additive and a ketone as the directing group.

Rhodium(III)-Catalyzed Regioselective Direct C4-Alkylation and C2-Annulation of Indoles: Straightforward Access to Indolopyridone

A straightforward RhIII-catalyzed strategy was developed for the site-selective C4-alkylation and C2-annulation of indole by using electronically variable diazo esters. The transformation was accomplished with the assist of an oxime directing group at the C3 position of the indole core with wide scope and functional-group tolerance. The method directly provided an indolopyridone core. The selectivity was triggered by the reactivity of the diazo coupling partner.

Meridianin D Analogues Display Antibiofilm Activity against MRSA and Increase Colistin Efficacy in Gram-Negative Bacteria

In the last 30 years, development of new classes of antibiotics has slowed, increasing the necessity for new options to treat multidrug resistant bacterial infections. Development of antibiotic adjuvants that increase the effectiveness of currently available antibiotics is a promising alternative approach to classical antibiotic development. Reports of the ability of the natural product meridianin D to modulate bacterial behavior have been rare. Herein, we describe the ability of meridianin D to inhibit biofilm formation of methicillin-resistant Staphylococcus aureus (MRSA) and to increase the potency of colistin against colistin-resistant and sensitive Gram-negative bacteria. Analogues were identified that are capable of inhibiting and dispersing MRSA biofilms and lowering the colistin MIC to below the CLSI breakpoint against Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli.

Regiocontrolled direct C4 and C2-methyl thiolation of indoles under rhodium-catalyzed mild conditions

A straightforward Rh(iii)-catalyzed general strategy was developed for the site-selective remote C4 (sp2) and C2 (sp3)-methyl thiolation of an indole core, keeping the oxime directing group at the C3 position. The transformation was accomplished under mild conditions with a wide scope and functional group tolerance. The directing group can easily be removed after operation. Methyl substitution at the C2 position of the indole core led to C2 (sp3)-methyl thiolation.