65435-04-3

Basic information

• Product Name: 5-CHLOROACETYLOXINDOLE
• Synonyms: 5-CHLOROACETYLOXINDOLE;(5-CHLOROACETYL)-1,3-DIHYDRO-2H-INDOL-2-ONE;2H-Indol-2-one, 5-(chloroacetyl)-1,3-dihydro- (9CI);5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one 98%;1H-indol-5-yl 2-chloroacetate;2H-Indol-2-one,5-(2-chloroacetyl)-1,3-dihydro-;5-(2-chloroacetyl)indolin-2-one;5-(Chloroacetyl)-2-oxindole
• CAS NO: 65435-04-3
• Molecular Formula: C₁₀H₈ClNO₂
• Molecular Weight: 209.63
• Product Categories: ACETYLHALIDE;blocks;IndolesOxindoles
• Mol File: 65435-04-3.mol
• Article Data: 40

Chemical Properties

• Melting Point: 228-232°C
• Boiling Point: 460.8°C at 760 mmHg
• Flash Point: 232.5°C
• Appearance: /
• Density: 1.361g/cm³
• Vapor Pressure: 1.13E-08mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: slightly sol. in Dimethylformamide
• PKA: 13.29±0.20(Predicted)
• CAS DataBase Reference: 5-CHLOROACETYLOXINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLOROACETYLOXINDOLE(65435-04-3)
• EPA Substance Registry System: 5-CHLOROACETYLOXINDOLE(65435-04-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 65435-04-3(Hazardous Substances Data)

Usage

Description

5-CHLOROACETYLOXINDOLE is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its chloroacetyl and oxindole functional groups, which contribute to its reactivity and potential applications in the field of medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
5-CHLOROACETYLOXINDOLE is used as a key intermediate for the synthesis of [(dihydrooxoindolylidene)methyl]pyrrolepropanoic acid and pyrido[2,3-d]pyrimidine. These compounds are known as tyrosine kinase inhibitors, which play a significant role in the development of targeted therapies for various diseases, including cancer.
As a precursor in the synthesis of tyrosine kinase inhibitors, 5-CHLOROACETYLOXINDOLE contributes to the development of novel drugs that can potentially inhibit the activity of tyrosine kinases, which are often overexpressed or mutated in cancer cells. By targeting these enzymes, these inhibitors can help regulate cell signaling pathways and prevent uncontrolled cell growth, ultimately leading to the suppression of tumor development and progression.

InChI:InChI=1/C10H8ClNO2/c11-5-9(13)6-1-2-8-7(3-6)4-10(14)12-8/h1-3H,4-5H2,(H,12,14)

Upstream product

• 118289-70-6 5-(chloroacetyl)-N-ethyloxindole 
• 59-48-3 2-oxoindole 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 102386-52-7 5-[2-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetyl]oxindol hydrochloride 
• 145737-34-4 5-(2-(3,4-dimethoxyphenyl)thiazol-4-yl)indolin-2-one 
• 61394-49-8 ethyl 2-oxindoline-5-carboxylate 
• 199328-10-4 methyl 2-oxoindoline-5-carboxylate 

Relevant articles and documents

CONJUGATES OF AMPK INHIBITORS AND PROTAC DEGRADERS AND RELATED USES

The present disclosure relates to compounds of Formula (I): T-L-D, stereoisomers thereof, prodrugs thereof, and pharmaceutically acceptable salts thereof, wherein T is an AMPK inhibiting moiety; L is a linking moiety; and D is a PROTAC degrading moiety. The present disclosure also relates to uses of the compounds, e.g., to inhibit AMP-Activated protein kinase (AMPK), degrading AMPK protein, and/or treat cancer in a subject.

AMP-ACTIVATED PROTEIN KINASE INHIBITORS AND METHODS OF MAKING AND USING THE SAME

The present disclosure relates to compounds of Formula (I): (I); stereoisomers thereof, prodrugs thereof, and pharmaceutically acceptable salts thereof. The present disclosure also relates to uses of the compounds, e.g., to inhibit AMP-Activated protein kinase (AMPK) and treat cancer in a subject.

Substituted oxindol-3-ylidenes as AMP-activated protein kinase (AMPK) inhibitors

AMP-activated protein kinase (AMPK) is a central metabolic regulator that promotes cancer growth and survival under hypoxia and plays a role in the maintenance of cancer stem cells. A major challenge to interrogating the potential of targeting AMPK in cancer is the lack of potent and selective small molecule inhibitors. Compound C has been widely used as an AMPK inhibitor, but it lacks potency and has a poor selectivity profile. The multi-kinase inhibitor, sunitinib, has demonstrated potent nanomolar inhibition of AMPK activity and has scope for modification. Here, we have designed and synthesized several series of oxindoles to determine the structural requirements for AMPK inhibition and to improve selectivity. We identified two potent, novel oxindole-based AMPK inhibitors that were designed to interact with the DFG motif in the ATP-binding site of AMPK, this key feature evades interaction with the common recptor tyrosine kinase targets of sunitinib. Cellular engagement of AMPK by these oxindoles was confirmed by the inhibition of phosphorylation of acetyl-CoA carboxylase (ACC), a known substrate of AMPK, in myeloid leukemia cells. Interestingly, although AMPK is highly expressed and activated in K562 cells these oxindole-based AMPK inhibitors did not impact cell viability or result in significant cytotoxicity. Our studies serve as a platform for the further development of oxindole-based AMPK inhibitors with therapeutic potential.