1160293-25-3

Basic information

• Product Name: 1-(2-chloroacetyl)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester
• Synonyms: 1-(2-chloroacetyl)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester;Methyl 1-(2-chloroacetyl)-2-oxoindoline-6-carboxylate;1H-Indole-6-carboxylic acid, 1-(2-chloroacetyl)-2,3-dihydro-2-oxo-, methyl ester;methyl 1-(chloroacetyl)-2-oxoindolin-6-ylcarboxylate
• CAS NO: 1160293-25-3
• Molecular Formula: C₁₂H₁₀ClNO₄
• Molecular Weight: 267.6651
• Mol File: 1160293-25-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 516.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.434±0.06 g/cm3(Predicted)
• PKA: -2.12±0.20(Predicted)
• CAS DataBase Reference: 1-(2-chloroacetyl)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-chloroacetyl)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester(1160293-25-3)
• EPA Substance Registry System: 1-(2-chloroacetyl)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester(1160293-25-3)

Safety Data

• Hazardous Substances Data: 1160293-25-3(Hazardous Substances Data)

Usage

General Description

1-(2-chloroacetyl)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester is a chemical compound with the molecular formula C13H11ClNO4. It is a methyl ester derivative of a carboxylic acid and contains a chloroacetyl group, as well as an indole ring structure. 1-(2-chloroacetyl)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester has potential pharmaceutical applications, as it may exhibit biological activity due to its structural features. The methyl ester allows for increased solubility in organic solvents, making it useful for pharmaceutical formulation. However, its exact uses and properties would need to be further studied and characterized.

Upstream product

• 14192-26-8 2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester 
• 79-04-9 chloroacetyl chloride 
• 541-88-8 Chloroacetic anhydride 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 1160293-27-5 [4-(methoxycarbonyl)-2-nitrophenyl]malonic acid dimethyl ester 
• 14719-83-6 methyl 3-nitro-4-chlorobenzoate 
• 618-95-1 methyl 3-nitrobenzoate 
• 121-92-6 3-nitrobenzoic acid 
• 334952-07-7 4-methoxycarbonylmethyl-3-nitrobenzoic acid methyl ester 
• 199328-10-4 methyl 2-oxoindoline-5-carboxylate 

Downstream Products

• 1160293-24-2 N-chloroacetyl-3-[methoxy(phenyl)methylene]-2-oxoindoline-6-carboxylic acid methyl ester 
• 1160293-22-0 3-[methoxy(phenyl)methylene]-2-oxoindoline-6-carboxylic acid methyl ester 
• 1987887-92-2 methyl (Z)-3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate 

Relevant articles and documents

Indolone derivative and pharmaceutical application thereof

The invention provides an indolone derivative and pharmaceutical application thereof. The structure of the indolone derivative is shown as a formula (A). Experimental results show that the compound provided by the invention has obviously improved pharmacokinetic properties than BIBF1120, has excellent inhibition effects on VEGFR, FGFR and PDGFR, can be used as a VEGFR, FGFR and/or PDGFR inhibitor,an angiogenesis inhibitor and a drug for preventing and/or treating various tumors including pharyngeal squamous cell carcinoma, and has a wide application prospect.

Novel 6-methoxycarbonyl indolinones bearing a pyrrole Mannich base moiety as angiokinase inhibitors

Inhibition of tumor angiogenesis through simultaneously disturbing vascular endothelial growth factor (VEGF) and platelet-derived growth factor (PDGF) mediated signaling pathways is a well-established approach in intervention of tumor. A series of 6-methoxycarbonyl indolinones bearing a pyrrole Mannich base moiety were synthesized and evaluated as potent angiokinase inhibitors. Compound 8a demonstrated favorable enzymatic activity against all subtypes of VEGFR and PDGFR. Also, it potently suppressed proliferation of HT-29 cells by inducing apoptosis. Compound 8a has emerged as a promising lead compound for development of angiokinase inhibitors targeting VEGFR and PDGFR.

Preparation method of crystalline nintedanib esylate

The invention discloses a preparation method of crystalline nintedanib esylate (3-Z-[1-(4-(N-((4-methyl-piperazin-1-yl)-methylcarbonyl)-N-methyl-amino)-phenylamino)-1-phenyl-methylene]-6-methoxycarbonyl-2-dihydroindolone monoethyl sulfonate). The method comprises steps as follows: (1) a compound represented in the formula (B) and acylating chlorination reagent chloroacetic anhydride react, and acyl chloride (C) is obtained; (2) the compound represented in the formula (C) and trimethyl orthobenzoate have a condensation reaction, and a compound represented in the formula (D) is obtained; (3) the compound represented in the formula (D) is deprotected, and a compound represented in the formula (E) is obtained; (4) the compound represented in the formula (E) and N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl) acetamide have a condensation reaction, and a compound represented in the formula (F) is obtained; (5) the compound represented in the formula (F) and ethanesulfonic acid have a salification reaction, and a nintedanib esylate compound represented in the formula (A) is obtained. The stable crystalline nintedanib esylate can be obtained with the method, technological conditions are mild, aftertreatment is simple, the purity is high, the reaction cost is low, and industrial production is easy to realize.