1677-47-0

Basic information

• Product Name: 4,5-DICHLORO-1H-INDOLE-2,3-DIONE
• Synonyms: 4,5-DICHLORO-1H-INDOLE-2,3-DIONE;4,5-DICHLOROISATIN;BUTTPARK 50\07-97;4,5-Dichloroindoline-2,3-dione
• CAS NO: 1677-47-0
• Molecular Formula: C₈H₃Cl₂NO₂
• Molecular Weight: 216.02
• Product Categories: Indoles and derivatives
• Mol File: 1677-47-0.mol

Chemical Properties

• Appearance: /
• Density: 1.643g/cm³
• Refractive Index: 1.637
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4,5-DICHLORO-1H-INDOLE-2,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DICHLORO-1H-INDOLE-2,3-DIONE(1677-47-0)
• EPA Substance Registry System: 4,5-DICHLORO-1H-INDOLE-2,3-DIONE(1677-47-0)

Safety Data

• Hazardous Substances Data: 1677-47-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,5-Dichloro-1H-indole-2,3-dione is used as a chemical intermediate for the development of new drugs and pharmaceutical products. Its unique reactivity and ability to participate in various chemical reactions make it a promising candidate for the creation of novel therapeutic agents.
Used in Organic Chemistry Research:
In the field of organic chemistry, 4,5-Dichloro-1H-indole-2,3-dione is used as a research compound to study and advance the understanding of chemical reactions and synthesis processes. Its versatility in undergoing different types of reactions contributes to the exploration of new synthetic pathways and methodologies.
Used in Laboratory Synthesis:
4,5-Dichloro-1H-indole-2,3-dione is used as a key intermediate in the synthesis of a variety of organic compounds in laboratory settings. Its presence in the synthesis process is crucial for the production of specific target molecules, highlighting its importance in the realm of chemical synthesis.

InChI:InChI=1/C8H3Cl2NO2/c9-3-1-2-4-5(6(3)10)7(12)8(13)11-4/h1-2H,(H,11,12,13)

Upstream product

• 6344-05-4 4-chloroisatin 
• 6662-53-9 N-(α-Oximino-acetyl)-3.4-dichlor-anilin 
• 115-17-3 bromal 
• 95-76-1 m,p-dichloroaniline 
• 1081809-48-4 (2E)-N-(3,4-dichlorophenyl)-2-hydroxyimino-acetamide 

Downstream Products

• 857601-95-7 6-(carboxymethyl-amino)-2,3-dichloro-benzoic acid 
• 68475-42-3 anagrelide 
• 58579-51-4 anagrelide hydrochloride 
• 70406-92-7 N-(6-amino-2,3-dichlorobenzyl)glycine ethyl ester 
• 70380-51-7 3,4-dichloro-2-hydroxymethylaniline 
• 1164112-22-4 C₁₈H₁₅Cl₂N₃O₅ 
• 847866-81-3 4,5-dichloro-3-hydroxy-3-(2-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-one 
• 122509-73-3 4,5-dichloroindole 
• 20776-60-7 6-amino-2,3-dichlorobenzoic acid 

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.

Synthesis and antifungal activity of 1-aminomethyl-3-{4- (chlorobenzyloxy) benzoylhydrazono}-4, 5/5, 6-dichloroindolin-2- ones

3-{4-(Chlorobenzyloxy) benzoylhydrazono}-4,5/5,6-dichloroindolin-2-ones 1a,b-5a,b, were synthesized by the condensation of 4-(chlorobenzyloxy) benzoylhydrazines and 4, 5/5, 6-dichloroindolin-2,3-diones. Compounds 1a,b-5a,b when subjected to Mannich reaction with secondary heterocyclic amines in the presence of formaldehyde, furnished 1-aminomethyl-3-{4-(chlorobenzyloxy) benzoylhydrazono}-4, 5/5, 6-dichloroindolin-2- ones 6a,b-20a,b. The structures of the compounds have been established by means of spectral (IR and 1H NMR) and elemental analysis. The compounds have been screened for their antifungal potential against human pathogenic fungi.

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.

Glycine receptor antagonist pharmacophore

Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer''s disease, amyotrophic lateral sclerosis, Huntington''s disease and Down''s syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions and inducing anesthesia are disclosed by administering to an animal in need of such treatment a compound which has high binding to the glycine receptor.

Imidazobenzodiazepines

There are described novel pharmaceutically active substances which have a pronounced affinity to the central benzodiazepine receptors and which have only a low toxicity.These active substances, namely imidazobenzodiazepines of the formula STR1 wherein A is lower alkylene, n is zero or 1, R 1 is lower alkynyl, lower alkenyl, aryl, (C 3-8)-cycloalkyl optionally substituted by lower alkyl or (C 5-8)-cycloalkenyl optionally substituted by lower alkyl, or a 5- or 6-membered saturated or unsaturated heterocycle which contains an oxygen or sulphur atom as a ring member and which is optionally substituted by lower alkyl, R 4 and R 5 each are hydrogen, halogen, trifluoromethyl, cyano, nitro, amino or lower alkyl and either R 2 is hydrogen and R 3 is lower alkyl or R 2 and R 3 together are dimethylene, trimethylene or propenylene, the compounds of formula I in which R 2 and R 3 together are dimethylene, trimethylene or propenylene having the (S) or (R,S) configuration with reference to the carbon atom denoted by γ,and their pharmaceutically acceptable acid addition salts, can be used as medicaments in the form of pharmaceutical preparations, especially in the control of convulsions and anxiety states and/or in the partial or complete antagonization of some or all activities which 1,4-benzodiazepines having tranquillizing activity or other substances display via the central benzodiazepine receptors.

Alkyl 5,6-dichloro-3,4-dihydro-2(1H)-iminoquinazoline-3-acetate hydrohalides

The known blood platelet antiaggregative agent 6,7-dichloro-1,5-dihydroimidazo[2,1-b]quinazolin-2(3H)-one is prepared in high yield via an improved process involving a novel intermediate of the Formula STR1 in which R1 is (lower)alkyl and X is bromo, chloro or iodo. Two processes for the preparation of compounds of the Formula III are disclosed, one of which involves the novel intermediate STR2