6341-92-0

Usage

Chemical Properties

Orange powder

InChI:InChI=1S/C8H4ClNO2/c9-4-1-2-5-6(3-4)10-8(12)7(5)11/h1-3H,(H,10,11,12)

Upstream product

• 79-37-8 oxalyl dichloride 
• 141-85-5 3-chloroaniline hydrochloride 
• 98591-63-0 7-chloro-1,2,3,4-tetrahydroquinoline-2,3,4-trione 3-oxime 
• 17122-55-3 Ν-(3-chlorophenyl)-2-hydroxyiminoacetamide 
• 108-42-9 3-chloro-aniline 
• 98-86-2 acetophenone 
• 6344-05-4 4-chloroisatin 
• 1189051-98-6 4-chloro-2-nitro-1-[2-iodoethynyl]benzene 
• 302-17-0 chloral hydrate 
• 6828-35-9 5-chloro-2-iodoaniline 
• 17422-33-2 6-chloroindole 
• 52537-00-5 6-chloroindoline 
• 1261152-95-7 6-chloro-3-iminoindolin-2-one 
• 89-61-2 2,5-dichloronitrobenzene 

Downstream Products

• 130420-81-4 6-chloro-1-morpholinomethylisatin 
• 5900-58-3 2-amino-4-chloro-benzoic acid methyl ester 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 77603-39-5 9-chloroindolo[2,1-b]quinoxazoline-6,12-dione 
• 77603-40-8 1,9-Dichloro-indolo[2,1-b]quinazoline-6,12-dione 
• 124028-88-2 7-chloro-3-(2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-4-carboxylic acid 
• 122750-40-7 4-Methoxy-benzoic acid [6-chloro-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide 
• 124930-81-0 6-Chloro-3-[(Z)-4-chloro-phenylimino]-1,3-dihydro-indol-2-one 
• 124930-82-1 6-Chloro-3-[(Z)-4-methoxy-phenylimino]-1,3-dihydro-indol-2-one 
• 122750-39-4 4-Hydroxy-benzoic acid [6-chloro-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide 
• 4341-53-1 6-chloro-1H-indole-2,3-dione-3-thiosemicarbazone 
• 122750-38-3 4-Chloro-benzoic acid [6-chloro-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide 
• 124031-95-4 6-chloro-3-(6'-chloro-2'-hydrazonobenzothiazolyl)-2-indolinone 
• 95060-67-6 6-Chloro-3-(dimethyl-hydrazono)-1,3-dihydro-indol-2-one 

Relevant academic research and scientific papers

Discovery of Isatin-Based Carbohydrazones as Potential Dual Inhibitors of Fatty Acid Amide Hydrolase and Monoacylglycerol Lipase

Using ligand-based design strategy, a set of isatin-3-carbohydrazones was designed, synthesized and evaluated for dual fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL) inhibition properties. Compound 5-chloro-N′-(5-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 b) emerged as a potent MAGL inhibitor with nanomolar activity (IC50=3.33 nM), while compound 5-chloro-N′-(1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 j) was the most potent selective FAAH inhibitor (IC50=37 nM). Compound 5-chloro-N′-(6-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 c) showed dual FAAH-MAGL inhibitory activity with an IC50 of 31 and 29 nM respectively. Enzyme kinetics studies revealed that the isatin-based carbohydrazones are reversible inhibitors for both FAAH and MAGL. Further, blood-brain permeability assay confirmed that the lead compounds (13 b, 13 c, 13 g, 13 m and 13 q) are suitable as CNS candidates. Molecular dynamics simulation studies revealed the putative binding modes and key interactions of lead inhibitors within the enzyme active sites. The lead dual FAAH-MAGL inhibitor 13 c showed significant antioxidant activity and neuroprotection in the cell-based cytotoxicity assay. In summary, the study yielded three potent FAAH/MAGL inhibitor compounds (13 b, 13 c and 13 j) with acceptable pharmacokinetic profile and thus can be considered as promising candidates for treating neurological and mood disorders.

Synthesis of substituted tryptanthrin via aryl halides and amines as antitumor and anti-MRSA agents

The natural alkaloid, tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione), and its analogues are found to exhibit potent antitumor and anti-MRSA activities. An efficient and convenient method has been developed for the synthesis of tryptanthrin D-ring derivatives through the reaction of substituted tryptanthrins and secondary amines in moderate to good yields. Some of the new compounds exhibited antitumor activities against the human tumor cell lines A549, HCT116 and MDA-MB-231, with mean IC50 values at low micromolar levels. In addition, some of the compounds showed excellent anti-MRSA activities and were more effective than vancomycin, with MIC values of 0.31–1.25 μg/mL for Mu50,RN4220, and Newman strains.

Synthesis and biological evaluation of novel 2-oxo-1,2-dihydroquinoline-4-carboxamide derivatives for the treatment of esophageal squamous cell carcinoma

No new and effective treatments have been approved for the treatment of esophageal squamous cell carcinoma (ESCC) in the past decade. Cisplatin and 5-fluoruracil are the most commonly used drugs for this disease. In order to develop a new class of drugs effective in our ESCC phenotypic screens, we began a systematic approach to generate novel compounds based on the 2-oxo-1,2-dihydroquinoline-4-carboxamide fragment. Herein, we report on the synthesis and initial assessment of 55 new analogues in two ESCC cell lines. Some of the active analogues with IC50 values around 10 μM were tested in three additional cell lines. Our structure-activity relationships revealed remarkable alterations in the anti proliferative activities upon modest chemical modifications and autophagy modulation is a suggested mechanism of action.

An efficient method based on indoles for the synthesis of isatins by taking advantage of I2O5 as oxidant

An efficient method to synthesize isatins based on indoles by using inorganic hypervalent I2O5 has been explored in good yields, which successfully realized the transformation from indoles to isatins under metal-free, mild condition

A Benzisoelenazolone modified pyrrole methyl ester substituted indole ketone compound and use thereof

The invention discloses a benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound and a use thereof. The invention depends on and claims the priority of a Chinese patent application 201110105248.0 submitted on April 26, 2011. Through reference, all contents of the Chinese patent application 201110105248.0 are incorporated into the invention. The benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound is shown in the general formula I. The 2-indolone compound provided by the invention has excellent antitumor activity and can be widely used for preparation of antitumor drugs.

Synthesis of diverse isatins: Via ring contraction of 3-diazoquinoline-2,4-diones

An efficient synthesis of diverse isatin derivatives was accomplished by a copper-mediated reaction of 3-diazoquinoline-2,4-diones via ring contraction through domino Wolff rearrangement, decarboxylation, bromination, substitution, and dehydration. This protocol has several advantages as a one-pot procedure, with functional group tolerance, and high yield.

Utilizing Solubility differences to achieve regiocontrol in the synthesis of substituted quinoline-4-carboxylic acids

A practical method for the regiocontrolled synthesis of substituted quinoline-4-carboxylic acids is described. Solubility differences between the product quinoline regioisomers enable their facile separation, thus avoiding any challenging chromatographic purifications and allowing access to highly substituted quinoline compounds in three steps from commercially available anilines.

A Palladium-Catalyzed Double Carbonylation Approach to Isatins from 2-Iodoanilines

A high-yielding procedure for the synthesis of isatins has been developed. Sequential Pd-catalyzed double carbonylation of 2-iodoanilines with near stoichiometric amounts of CO followed by acid-promoted cyclization readily affords an array of isatins. The conversion of 2-iodoanilines to isatins in good to excellent yields was found to proceed with good functional group tolerance. This protocol proved adaptable to 13C-isotope labeling of isatins, which was extended to the synthesis of the 13C-isotope labeled antiviral drug metisazone and the experimental anti-schizophrenia drug ML137.

A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: Construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters

A cinchona alkaloid catalyzed diastereoselective and enantioselective sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and isoindigos has been successfully developed to afford the highly congested bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters in high yields (up to 91%), excellent diastereoselectivities (up to >20 : 1 dr), and good enantioselectivities (up to 98% ee). Some synthetic transformations of the reaction products were also studied.

Copper-catalyzed base-accelerated direct oxidation of C-H bond to synthesize benzils, isatins, and quinoxalines with molecular oxygen as terminal oxidant

We describe herein an efficient and general copper (II)-catalyzed base-accelerated oxidation of the C-H bond to synthesize benzils and isatins. With similar oxidation system an efficient one-pot procedure for the synthesis of quinoxaline derivatives was realized. The two protocols feature using molecular oxygen as terminal oxidant, low catalyst loading, wide substrate scope, and high functional-group tolerance.