306279-75-4

Basic information

• Product Name: 1-(2-CHLOROBENZYL)-1H-INDOLE-2,3-DIONE
• Synonyms: AURORA 1496;1-(2-CHLOROBENZYL)-1H-INDOLE-2,3-DIONE;AKOS BBS-00008238;1H-indole-2,3-dione, 1-[(2-chlorophenyl)methyl]-;1-(2-chlorobenzyl)isatin;1-[(2-chlorophenyl)methyl]indole-2,3-dione;1-[(2-chlorophenyl)methyl]indoline-2,3-dione;1H-Indole-2,3-dione, 1-(2-chlorobenzyl)-
• CAS NO: 306279-75-4
• Molecular Formula: C₁₅H₁₀ClNO₂
• Molecular Weight: 271.7
• Mol File: 306279-75-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2-CHLOROBENZYL)-1H-INDOLE-2,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-CHLOROBENZYL)-1H-INDOLE-2,3-DIONE(306279-75-4)
• EPA Substance Registry System: 1-(2-CHLOROBENZYL)-1H-INDOLE-2,3-DIONE(306279-75-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 306279-75-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
1-(2-Chlorobenzyl)-1H-indole-2,3-dione is used as a research compound for its potential biological activities, including anti-inflammatory, analgesic, and antitumor properties. Its application in this field is driven by the need to explore and develop novel treatments for various diseases and conditions.
Used in Organic Synthesis:
As an intermediate in the synthesis of various organic compounds, 1-(2-Chlorobenzyl)-1H-indole-2,3-dione plays a crucial role in the development of new chemical entities with potential applications in different industries.
Used in Dye and Pigment Manufacturing:
1-(2-Chlorobenzyl)-1H-indole-2,3-dione is used as a key component in the manufacturing of dyes and pigments, leveraging its unique chemical structure and properties to create a wide range of colorants for various applications.

Upstream product

• 91-56-5 indole-2,3-dione 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 95-49-8 2-methylchlorobenzene 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 

Downstream Products

• 1426415-26-0 1-[(2-chlorophenyl)methyl]-5'-(3-methoxyphenyl)-1,2-dihydro-3'H-spiro[indole-3,2'-[1.3.4]thiadiazole]-2-one 
• 1426415-28-2 5'-(3-chlorophenyl)-1-[(2-chlorophenyl)methyl]-1,2-dihydro-3'H-spiro[indole-3,2'-[1.3.4]thiadiazole]-2-one 
• 1426415-32-8 1-[(2-chlorophenyl)methyl]-5'-(2-methylphenyl)-1,2-dihydro-3'H-spiro[indole-3,2'-[1.3.4]thiadiazole]-2-one 
• 1621419-52-0 C₃₉H₄₀ClN₃O₄ 
• 1621376-28-0 1-(2-chlorobenzyl)-3-hydroxy-3-(5-methoxy-1H-indol-3-yl)indolin-2-one 
• 1621376-23-5 3-(5-bromo-1H-indol-3-yl)-1-(2-chlorobenzyl)-3-hydroxyindolin-2-one 
• 676612-45-6 1-(2-chlorobenzyl)-3-hydroxy-3-(1H-indol-3-yl)indolin-2-one 
• 1450991-62-4 C₁₆H₁₂ClN₅O₂ 

Relevant articles and documents

Synthesis and biological evaluation of isatin derivatives containing 1,3,4-thiadiazole as potent a-glucosidase inhibitors

A series of (Z)-3-(2-(1,3,4-thiadiazol-2-yl)hydrazono)-1-substituted indolin-2-ones derivatives (3a-3m) were designed and synthesized. All newly synthesized compounds were evaluated for their a-glucosidase inhibitory activity with resveratrol as positive control in vitro. Except for 3i and 3j, all of the compounds showed a potent inhibitory activity against a-glucosidase with IC50 values in the range of 3.12 ± 1.25 to 45.95 ± 1.26 μM and the purity of these compounds was greater than 95%. The IC50 values were being compared to the standard resveratrol (IC50 = 22.00 ± 1.15 μM) and it was found that compounds 3b, 3d-3h were found to be more active than resveratrol. Specifically, (Z)-3-(2-(1,3,4-thiadiazol-2-yl)hydrazono)-1-(4-chlorobenzyl)indolin-2-one (3d) exhibited the most potent a-glucosidase inhibitory activity with IC50 value of 3.12 ± 1.25 μM. The kinetic analysis revealed that compound (3d) is noncompetitive inhibitor. Structure activity relationship has been established for all compounds. Furthermore, the binding interactions of compound 3d with the active site of a-glucosidase were confirmed through molecular docking. This study has identified a new class of potent a-glucosidase inhibitors for further investigation.

Synthesis, in vitro α-glucosidase inhibitory activity and docking studies of novel chromone-isatin derivatives

A novel series of chromone-isatin derivatives 6a–6p were designed, synthesized and characterized by 1H NMR, 13C NMR and HRMS. These novel synthetic compounds were evaluated for inhibitory activity against yeast α-glucosidase enzyme. The results of biological test have shown that all tested compounds exhibited excellent to potent inhibitory activity in the range of IC50 = 3.18 ± 0.12–16.59 ± 0.17 μM as compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Compound 6j (IC50 = 3.18 ± 0.12 μM) with a hydroxyl group at the 7-position of chromone and a 4-bromobenzyl group at the N1-positions of isatin, was found to be the most active compound among the series. Furthermore, molecular docking study was performed to help understand binding interactions of the most active analogs with α-glucosidase enzyme. These results indicated that this class of compounds had potential for the development of anti-diabetic agents.

THERAPEUTIC COMPOUNDS AND METHODS

The invention provides compounds of formula I: and salts thereof. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for treating cancer using compounds of formula I.

OXINDOLE COMPOUNDS AND THEIR USES AS THERAPEUTIC AGENTS

This invention is directed to oxindole compounds that are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of using the compounds are also disclosed.

De novo design and synthesis of HIV-1 integrase inhibitors

Existing AIDS therapies are out of reach for most HIV-infected people in developing countries and, where available, they are limited by their toxicity and their cost. New anti-HIV agents are needed urgently to combat emerging viral resistance and reduce the side effects associated with currently available drugs. Toward this end, LeapFrog, a de novo drug design program was used to design novel, potent, and selective inhibitors of HIV-1 integrase. The designed compounds were synthesized and tested for in vitro inhibition of HIV-1 integrase. Out of the 25 compounds that were designed, and synthesized, four molecules (compounds 23, 26, 43, and 59) showed moderate to low inhibition of HIV-1 integrase for 3′-processing and 3′- strand transfer activities. Nonetheless, these compounds possess structural features not seen in known HIV-1 integrase inhibitors and thus can serve as excellent leads for further optimization of anti-HIV-1 integrase activity.