6344-05-4

Basic information

• Product Name: 4-CHLOROISATIN
• Synonyms: 4-CHLORO-2,3-INDOLINEDIONE;4-CHLOROISATIN;4-CHLOROINDOLE-2,3-DIONE;BUTTPARK 50\07-90;4-Chloro-(1H)-indole-2,3-dione;4-Chloro-2,3-dihydro-1H-indole-2,3-dione;4-chloro-1H-indole-2,3-dione(SALTDATA: FREE);4-Chloroindole-2,3-dione 4-Chloro-2,3-indolinedione
• CAS NO: 6344-05-4
• Molecular Formula: C₈H₄ClNO₂
• Molecular Weight: 181.58
• EINECS: 1533716-785-6
• Product Categories: Indane/Indanone and Derivatives;Indoles;Simple Indoles
• Mol File: 6344-05-4.mol

Chemical Properties

• Melting Point: 258 °C
• Appearance: /
• Density: 1.519 g/cm³
• Refractive Index: 1.626
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Dimethylformamide
• PKA: 9.44±0.20(Predicted)
• CAS DataBase Reference: 4-CHLOROISATIN(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROISATIN(6344-05-4)
• EPA Substance Registry System: 4-CHLOROISATIN(6344-05-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 6344-05-4(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
4-Chloroisatin is used as a plant growth regulator for enhancing crop yield and quality by modulating plant growth and development.
Used in Pharmaceutical Industry:
4-Chloroisatin is used as a selective inhibitor of carboxylesterases for potential applications in the treatment of various diseases and conditions where carboxylesterase activity plays a role, such as certain cancers and neurological disorders.

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

Upstream product

• 108-42-9 3-chloro-aniline 
• 302-17-0 chloral hydrate 
• 98-86-2 acetophenone 
• 17122-55-3 Ν-(3-chlorophenyl)-2-hydroxyiminoacetamide 

Downstream Products

• 130420-80-3 4-chloro-1-morpholinomethylisatin 
• 122750-36-1 4-Methoxy-benzoic acid [4-chloro-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide 
• 124930-77-4 4-Chloro-3-[(Z)-4-chloro-phenylimino]-1,3-dihydro-indol-2-one 
• 878479-69-7 (2-Ethyl-phenoxy)-acetic acid [4-chloro-2-oxo-1,2-dihydro-indol-(3E)-ylidene]-hydrazide 
• 139516-68-0 C₂₀H₂₀ClN₅O₂S 
• 729597-47-1 N-(3-chloro-2-carboxy-phenyl)glycine 
• 20870-77-3 4-chloroindolin-2-one 
• 6341-92-0 6-chloroisatin 
• 1357391-13-9 3(RS)4(RS)-methyl 4-chloro-2-oxo-4'-phenyl-4'H-spiro[indoline-3,5'-oxazole]-4'-carboxylate 

Relevant articles and documents

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.

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.

Cyclization of cyanoethylated ketones as a route to 6-substituted indole derivatives

δ-Cyanoketones are quickly cyclized with KOtBu to 3-aminocyclohex-2-enone derivatives, which in turn will give substituted indoles when treated with oxalyl chloride. Thus, 3-amino-6,6-dimethylcyclohex-2-enone gave 3-chloro-6,6-dimethyl-2,5,6,7-tetrahydroindole-2,5-dione, whose structure was corroborated by X-ray crystallography, whereas the corresponding molecule without the blocking gem-dimethyl groups, 3-aminocyclohex-2-enone, gave via hydrogen shifts 6-chloro-3-hydroxyoxindole.

Novel synthesis of 4-or 6-substituted indirubin derivatives

A simple and convenient route for synthesis of a series of 4-or 6-substituted indirubin derivatives by oxidation and subsequent condensation of indoxyl and isatin is described. Acidic reaction conditions are crucial to the condensation of 4-substituted derivatives, whereas for the condensation of 6-substituted derivatives, both acidic and basic conditions work well. Copyright Taylor & Francis Group, LLC.

Counter-current chromatography separation of isatin derivatives using the sandmeyer methodology

A rapid and efficient method, using high-speed counter-current chromatography (HSCCC) technique, was developed for the separation of isomeric isatin derivatives, prepared following the Sandmeyer route. The biphasic solvent system composed of hexane:ethyl acetate:ethanol:water 1:0.5:0.5:1 (v/v/v/v) was used for all separations.

Synthesis and antimicrobial evaluation of some 4- or 6-chloroisatin derivatives

Two series of chloroisatin-3-semicarbazones and hydrazones have been designed and prepared by condensing 4-chloro and 6-chloroisatin with several substituted semicarbazides and related bioisosteric hydrazides, respectively. Investigation of in vitro antimicrobial activity of compounds has been performed by agar double dilution method against nine pathogenic bacteria and four pathogenic fungi. The title compounds are also screened for their antitubercular activity against Mycobacterium tuberculosis H37 Rv using microplate alamar blue assay. Many of the synthesized compounds exhibit significant antibacterial activity in comparison to sulphamethoxazole, trimethoprim and some compounds show good antifungal activity comparable to clotrimazole. The semicarbazones arised from the 6-chloroisatin series have exhibited good antimicrobial activity than that obtained from 4-chloroisatins. Compounds, 6-chloroisatin-3-(2′-chlorophenyl) semicarbazones 1b and 6-chloroisatin-3-(4′-bromophenyl) semicarbazone 4b have shown a promising activity in both antibacterial and antifungal screenings. None of the compounds has been found to be active in antitubercular screening.

INDIRUBIN-TYPE COMPOUNDS, COMPOSITIONS, AND METHODS FOR THEIR USE

Compounds and compositions including 6-bromo-indirubin, 5-amino-indirubin and N-methyl-indirubins and related indirubin derivatives are provided that are useful as selective modulators of glycogen synthase kinase-3, cyclin-dependent protein kinases or aryl hydrocarbon receptors. Methods of inhibiting or modulating cell growth or cell cycling are provided using the compounds of the invention. In other aspects, compounds and methods for the treatment of protozoan-mediated diseases, Alzheimer's disease and diabetes are provided.

Structural Basis for the Synthesis of Indirubins as Potent and Selective Inhibitors of Glycogen Synthase Kinase-3 and Cyclin-Dependent Kinases

Pharmacological inhibitors of glycogen synthase kinase-3 (GSK-3) and cyclin-dependent kinases have a promising potential for applications against several neurodegenerative diseases such as Alzheimer's disease. Indirubins, a family of bis-indoles isolated from various natural sources, are potent inhibitors of several kinases, including GSK-3. Using the cocrystal structures of various indirubins with GSK-3β, CDK2 and CDK5/p25, we have modeled the binding of indirubins within the ATP-binding pocket of these kinases. This modeling approach provided some insight into the molecular basis of indirubins' action and selectivity and allowed us to forecast some improvements of this family of bis-indoles as kinase inhibitors. Predicted molecules, including 6-substituted and 5,6-disubstituted indirubins, were synthesized and evaluated as CDK and GSK-3 inhibitors. Control, kinase-inactive indirubins were obtained by introduction of a methyl substitution on N1.

Oxindole derivative

An oxindole of Formula 1 or a prodrug thereof, or a pharmaceutically acceptable salt thereof is useful for growth hormone releaser: wherein R1, R2, R3and R4are independently hydrogen, optionally substituted alkyl etc; R5is optionally substituted aryl or optionally substituted heteroaryl; Z is —O— or —NH—; one of W1and W2is hydrogen, alkyl or —Y—CON(R10)R11; the other of W1and W2is n is 1, 2 or 3; m is 0, 1, 2 or 3; Y is single bond or C1-C3alkylene; R6and R7are independently hydrogen, optionally substituted alkyl etc; R8and R9are independently hydrogen, optionally substituted alkyl etc; R10and R11are independently hydrogen, alkyl etc.