1677-48-1

Basic information

• Product Name: 5,6-dichloro-1H-indole-2,3-dione
• Synonyms: 5,6-Dichloroindoline-2,3-dione
• CAS NO: 1677-48-1
• Molecular Formula: C₈H₃Cl₂NO₂
• Molecular Weight: 216.02
• Mol File: 1677-48-1.mol

Chemical Properties

• Melting Point: 273-275℃
• Appearance: /
• Density: 1.643 g/cm³
• Refractive Index: 1.637
• Storage Temp.: 2-8°C
• PKA: 7.63±0.20(Predicted)
• CAS DataBase Reference: 5,6-dichloro-1H-indole-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-dichloro-1H-indole-2,3-dione(1677-48-1)
• EPA Substance Registry System: 5,6-dichloro-1H-indole-2,3-dione(1677-48-1)

Safety Data

• Hazardous Substances Data: 1677-48-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5,6-dichloro-1H-indole-2,3-dione is used as a building block in organic synthesis for the preparation of various pharmaceuticals and agrochemicals. Its unique chemical structure allows for the creation of a wide range of compounds with diverse applications.
Used in Pharmaceutical Industry:
5,6-dichloro-1H-indole-2,3-dione is used as a precursor in the development of pharmaceuticals. Its derivatives have been studied for their potential biological activities, such as anti-inflammatory, antioxidant, and anti-cancer properties. This makes it a valuable compound in the search for new drugs to treat various diseases and conditions.
Used in Agrochemical Industry:
5,6-dichloro-1H-indole-2,3-dione is also used in the agrochemical industry for the synthesis of various agrochemicals. Its derivatives may possess properties that can be beneficial in the development of pesticides, herbicides, or other agricultural chemicals to improve crop yield and protect against pests.
Used in Research and Development:
5,6-dichloro-1H-indole-2,3-dione is utilized in research and development for further exploration of its potential applications and properties. Its unique characteristics and reactivity make it an interesting compound for scientists to study and potentially discover new uses in various fields.

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

Upstream product

• 6341-92-0 6-chloroisatin 
• 6662-53-9 N-(α-Oximino-acetyl)-3.4-dichlor-anilin 
• 71293-59-9 5,6-dichloroindol-2-one 
• 95-76-1 m,p-dichloroaniline 
• 121859-57-2 5,6-dichloro-1H-indole 
• 1081809-48-4 (2E)-N-(3,4-dichlorophenyl)-2-hydroxyimino-acetamide 
• 215959-21-0 2-(4,5-Dichloro-2-nitro-phenyl)-malonic acid diethyl ester 
• 2339-78-8 1,2-dichloro-4-fluoro-5-nitrobenzene 
• 215959-31-2 3,3-Dibromo-5,6-dichloro-1,3-dihydro-indol-2-one 

Downstream Products

• 20776-61-8 2-amino-4,5-dichloro-benzoic acid 
• 865488-72-8 4-methyl-N'-(5,6-dichloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)benzenesulfonylhydrazide 
• 6958-39-0 6,7-dichloroquinazolin-4(3H)-one 
• 352278-23-0 5,6-dichloro-3-hydroxy-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one 
• 113525-09-0 2-(carboxymethyl-amino)-4,5-dichloro-benzoic acid 

Relevant articles and documents

Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides

Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.

Ruthenium-Catalyzed Asymmetric Allylic Alkylation of Isatins

A new ruthenium-based catalytic system for branched-selective asymmetric allylic alkylation is disclosed and applied to the synthesis of chiral isatin derivatives. The catalyst, which is generated in situ from commercially available CpRu(MeCN)3PF6 and a BINOL-derived phosphoramidite, is both highly active (TON up to 180) and insensitive to air and moisture. Additionally, the N-alkylated isatins accessible using this methodology are versatile building blocks that are readily transformed into chiral analogs of achiral drug molecules.

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 structure-activity relationship studies of small molecule disruptors of EWS-FLI1 interactions in Ewing's sarcoma

EWS-FLI1 is an oncogenic fusion protein implicated in the development of Ewing's sarcoma family tumors (ESFT). Using our previously reported lead compound 2 (YK-4-279), we designed and synthesized a focused library of analogues. The functional inhibition of the analogues was measured by an EWS-FLI1/NR0B1 reporter luciferase assay and a paired cell screening approach measuring effects on growth inhibition for human cells containing EWS-FLI1 (TC32 and TC71) and control PANC1 cell lines devoid of the oncoprotein. Our data revealed that substitution of electron donating groups at the para-position on the phenyl ring was the most favorable for inhibition of EWS-FLI1 by analogs of 2. Compound 9u (with a dimethylamino substitution) was the most active inhibitor with GI50 = 0.26 ± 0.1 μM. Further, a correlation of growth inhibition (EWS-FLI1 expressing TC32 cells) and the luciferase reporter activity was established (R2 = 0.84). Finally, we designed and synthesized a biotinylated analogue and determined the binding affinity for recombinant EWS-FLI1 (Kd = 4.8 ± 2.6 μM).

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.

1-Substituted pyrazolo[1,5-c]quinazolines as novel Gly/NMDA receptor antagonists: Synthesis, biological evaluation, and molecular modeling study

A new set of 5,6-dihydro-pyrazolo[1,5-c]quinazoline-2-carboxylates (2-18), bearing different substituents (COOEt, Cl, Br, CH3, and COOH) at position-1, were synthesized in order to investigate the influence of various groups at this specific position on Gly/NMDA receptor affinity and/or selectivity. All the herein reported compounds were evaluated for their binding at the Gly/NMDA, AMPA, and KA receptors. Some selected compounds were also tested for their functional antagonistic activity at both the AMPA and NMDA receptor-ion channels. The results obtained in this study have highlighted that a C-1 lipophilic substituent on the pyrazolo[1,5-c]quinazoline-2-carboxylate core shifts selectivity toward the Gly/NMDA receptor, while a C-1 anionic carboxylate residue is able to increase affinity toward this receptor subtype. In particular, the 2-carboxylic acids 15 and 16, bearing a chlorine atom at position-1, are not only potent (Ki = 0.18 and 0.16 μM, respectively), but also highly Gly/NMDA versus AMPA selective (selectivity ratio > 500). Furthermore, the 1,2-dicarboxylic acids 13 and 14 are endowed with the highest Gly/NMDA receptor binding activity (Ki = 0.09 and 0.059 μM, respectively), among the pyrazoloquinazoline series of derivatives. A molecular modeling study has been carried out to better understand receptor affinity and selectivity of these new pyrazoloquinazoline derivatives.

Phenylsulfonyl-1,3-dihydro-2h-indole-2-one derivatives, their preparation and their therapeutic use

The invention relates to compounds of formula: and also to the salts thereof with mineral or organic acids, and the solvates and/or hydrates thereof, with affinity for and selectivity towards the arginine-vasopressin V1b receptors and/or for the ocytocin receptors and, furthermore, for certain compounds, affinity for the V1a receptors. The invention also relates to the process for preparing them, to the intermediate compounds of formula (IV) that are useful for preparing them, to pharmaceutical compositions containing them and to their use for preparing medicinal products.

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.