53590-58-2

Usage

Chemical Properties

Light yellow solid

Upstream product

• 27034-51-1 ethyl 6-chloro-1H-indole-2-carboxylate 
• 16732-75-5 6-chloro-1H-indole-2-carboxylic acid 
• 98081-84-6 6-chloro-2-methoxycarbonylindole 
• 540523-98-6 3-(4-chloro-2-nitro-phenyl)-2-oxo-propionic acid ethyl ester 
• 89-59-8 4-chloro-2-nitrotoluene 

Downstream Products

• 53590-59-3 6-chloro-1H-indole-2-carbaldehyde 
• 1616101-46-2 7-chloro-1,2,4-triphenyl-9H-carbazole 
• 53590-49-1 5-chloro-1H-indole-2-carbaldehyde 
• 6127-17-9 6-chloro-2-methyl-1H-indole 
• 540524-03-6 methyl 4-{2-[2-{2-[(benzylsulfonyl)amino]ethyl}-6-chloro-1-(diphenylmethyl)-1H-indol-3-yl]ethoxy}benzoate 
• 540524-02-5 N-{2-[6-chloro-1-(diphenylmethyl)-1H-indol-2-yl]ethyl}-1-phenylmethanesulfonamide 
• 540524-01-4 {2-[6-chloro-1-(diphenylmethyl)-1H-indol-2-yl]ethyl}amine 
• 934285-82-2 6-chloro-1-(diphenylmethyl)-2-[(E)-2-nitrovinyl]-1H-indole 
• 540523-99-7 6-chloro-1-(diphenylmethyl)-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.

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.

FUSED-RING OR TRICYCLIC ARYL PYRIMIDINE COMPOUND USED AS KINASE INHIBITOR

Disclosed is a fused-ring or tricyclic aryl pyrimidine compound used as a mutation selectivity EGFR inhibitor. Specifically, disclosed is a compound represented by formula (I) and used as an EGFR inhibitor or a pharmaceutically acceptable salt thereof.

Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells

We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

One-Pot Base-Mediated Synthesis of Functionalized Aza-Fused Polycyclic Quinoline Derivatives

A new one-pot protocol has been developed for the facile and efficient synthesis of aza-fused polycyclic quinolines (e.g., pyrrolo[1,2-a]quinolines) by the base-catalyzed reaction of 2-formylpyrroles and 2-halophenylacetonitriles. This reaction proceeded under transition metal-free conditions and showed high functional group tolerance, with the desired products being formed in good yields.

Construction of Benzo[c]carbazoles and Their Antitumor Derivatives through the Diels-Alder Reaction of 2-Alkenylindoles and Arynes

The direct assembly of benzo[c]carbazole derivatives via the Diels-Alder reaction of arynes and easily accessible 2-alkenylidoles was reported. By employing different aryne precursor loads, 6,7-dihydrobenzo[c]carbazoles or aryl-substituted 7,11b-dihydrobenzo[c]carbazoles could be controllably generated in good to excellent yields under a nitrogen atmosphere. On the other hand, when the reaction was conducted under oxygen, oxidated/aromatized product benzo[c]carbazoles could be generated directly with high selectivity and efficiency in a one-step manner. Interestingly, the benzo[c]carbazole-5-carboxamide amidation derivatives of the above products showed good antitumor activities. The inhibitory effect of these molecules against cancer cells was also described.

Inhibition of 5-oxo-6,8,11,14-eicosatetraenoic acid-induced activation of neutrophils and eosinophils by novel indole oxe receptor antagonists

5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a 5-lipoxygenase product that is a potent granulocyte chemoattractant, which induces the infiltration of eosinophils into human skin when injected intradermally. It could therefore be an important proinflammatory mediator in eosinophilic diseases such as asthma and allergic rhinitis, and the OXE receptor, which mediates its actions, is therefore an attractive drug target. Using a structure-based approach in which substituents mimicking the essential polar (C1-C5) and hydrophobic (C15-C20) regions of 5-oxo-ETE were incorporated on an indole scaffold, we identified two potent selective OXE antagonists with IC50 values of about 30 nM. Neither compound displayed agonist activity and both inhibited 5-oxo-ETE-induced chemotaxis and actin polymerization and were relatively resistant to metabolism by rat liver homogenates. The active enantiomers of these racemic antagonists were even more potent, with IC50 values of 10 nM. These selective OXE antagonists could potentially be useful therapeutic agents in allergic diseases such as asthma.

Methods for the use of inhibitors of cytosolic phospholipase A2 in the treatment of thrombosis

This invention provides methods for the use of substituted indole compounds of the general formula: and pharmaceutically acceptable salt forms thereof. The invention provides methods for the use of the compounds in the treating or preventing thrombosis in a mammal, or preventing progression of symptoms of thrombosis.