199328-10-4

Basic information

• Product Name: Methyl oxindole-5-carboxylate
• Synonyms: 2-OXO-2,3-DIHYDRO-1H-INDOLE-5-CARBOXYLIC ACID METHYL ESTER;METHYL OXINDOLE-5-CARBOXYLATE;METHYL 2-OXINDOLE-5-CARBOXYLATE;METHYL 2-OXINDOLINE-5-CARBOXYLATE;Methyl 2-oxoindoline-5-carboxylate;Methyl oxindole-5-carboxylate 96%;Methyl-2-Dxoindline-5-carboxylate;Methyl 2-oxindole-5-carboxylate 96%
• CAS NO: 199328-10-4
• Molecular Formula: C₁₀H₉NO₃
• Molecular Weight: 191.18
• Product Categories: blocks;IndolesOxindoles;Indole/indoline/oxindole;Indole and Indoline;Indole;Indoles;Boronic Acid;Heterocyclic Compounds
• Mol File: 199328-10-4.mol

Chemical Properties

• Melting Point: 192-199
• Boiling Point: 405.6 °C at 760 mmHg
• Flash Point: 199.1 °C
• Appearance: /
• Density: 1.283 g/cm³
• Vapor Pressure: 8.67E-07mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.43±0.20(Predicted)
• CAS DataBase Reference: Methyl oxindole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl oxindole-5-carboxylate(199328-10-4)
• EPA Substance Registry System: Methyl oxindole-5-carboxylate(199328-10-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 199328-10-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Methyl oxindole-5-carboxylate is used as a research compound for its potential biological activities, including its anti-inflammatory, anti-cancer, and anti-bacterial properties. It is valued for its ability to inhibit certain enzymes and cell proliferation, which makes it a promising candidate for the development of new drugs.
Used in Drug Development:
In the pharmaceutical industry, methyl oxindole-5-carboxylate is utilized as a lead compound in drug discovery. Its capacity to modulate biological processes at the molecular level is being explored for the treatment of various diseases and conditions.
Used as a Chemical Intermediate:
Methyl oxindole-5-carboxylate serves as a crucial intermediate in the synthesis of a range of pharmaceutical compounds. Its chemical structure and functional groups facilitate the creation of new molecules with therapeutic potential, contributing to the advancement of medicinal chemistry.
Used in Medicinal Chemistry:
As a versatile chemical, methyl oxindole-5-carboxylate is applied in medicinal chemistry to explore its interactions with biological targets and to understand its mechanisms of action. This knowledge aids in optimizing its properties and developing it into effective therapeutic agents.

InChI:InChI=1/C10H9NO3/c1-14-10(13)6-2-3-8-7(4-6)5-9(12)11-8/h2-4H,5H2,1H3,(H,11,12)

Upstream product

• 3375-31-3 palladium diacetate 
• 193354-13-1 5-iodo-1,3-dihydro-indol-2-one 
• 67-56-1 methanol 
• 65435-04-3 5-chloroacetylindolin-2-one 
• 59-48-3 2-oxoindole 
• 102359-00-2 2-oxoindoline-5-carboxylic acid 
• 1160293-27-5 [4-(methoxycarbonyl)-2-nitrophenyl]malonic acid dimethyl ester 
• 201230-82-2 carbon monoxide 
• 619-45-4 4-methoxycarbonyl aniline 
• 222036-28-4 3-methylthio-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid methyl ester 
• 79-22-1 methyl chloroformate 

Downstream Products

• 1160293-25-3 methyl 1-(2-chloroacetyl)-2-oxoindoline-6-carboxylate 
• 1253769-05-9 (Z)-1-acetyl-3-(ethoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid methyl ester 
• 1609389-50-5 N-(2-amino-5-(thiophen-2-yl)phenyl)-2-cyclopropyl-1-(2-morpholinoethyl)-1H-indole-5-carboxamide 
• 1609390-64-8 C₃₃H₃₈N₄O₄S 

Relevant articles and documents

Synthesis and characterization of amino acid substituted sunitinib analogues for the treatment of AML

Acute myeloid leukemia (AML) is the most common type of leukemia in adults. Sunitinib, a multikinase inhibitor, was the first Fms-like tyrosine kinase 3 (FLT3) inhibitor clinically used against AML. Off-target effects are a major concern for multikinase inhibitors. As targeted delivery may reduce such undesired side effects, our goal was to develop novel amino acid substituted derivatives of sunitinib which are potent candidates to be used conjugated with antibodies and peptides. In the current paper we present the synthesis, physicochemical and in vitro characterization of sixty two Fms-like tyrosine kinase 3-internal tandem duplication (FLT3-ITD) mutant kinase inhibitors, bearing amino acid moieties, fit to be conjugated with peptide-based delivery systems via their carboxyl group. We determined the solubility, pKa, CHI and LogP values of the compounds along with their inhibition potential against FLT3-ITD mutant kinase and on MV4-11 cell line. The ester derivatives of the compounds inhibit the growth of the MV4-11 leukemia cell line at submicromolar concentration.

Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles

A Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles was achieved, affording a variety of multifunctional 3-ylideneoxindoles with good yields andZ/Eselectivities (64%-89% yield, 78?:?22->99?:?1Z/E). Importantly, an operationally simple, one-pot sequential catalytic synthesis of 3-ylideneoxindoles was also developed. Additionally, a cross [1,3]-rearrangement experiment and nonracemic transformation were also carried out, which indicated a concerted rearrangement mechanism of this methodology.

INDOLINONE DERIVATIVES AND PROCESS FOR THEIR MANUFACTURE

The present invention relates to specific indolinone derivatives, namely the compounds of formula, in which R1 represents an hydrogen atom or a group, and R2 and R3 each represent an hydrogen atom or R2 and R3 taken together represent a group, with the proviso that when R1 represents an hydrogen atom R2 and R3 taken together represent a group, and to a process for their manufacture.

3-heteroarylidene-2-indolinone protein kinase inhibitors

The present invention relates to novel 3-heteroarylidene-2-indolinone compounds and physiologically acceptable salts thereof which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

Pyrrole substituted 2-indolinone protein kinase inhibitors

The present invention relates to novel pyrrole substituted 2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

3-(cycloalkanoheteroarylidenyl)-2-indolinone protein tyrosine kinase inhibitors

The present invention relates to novel 3-(cycloalkano-heteroarylidenyl)-2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which are expected to modulate the activity of protein tyrosine kinases and therefore to be useful in the prevention and treatment of protein tyrosine kinase related cellular disorders such as cancer.

Oxindole-based inhibitors of cyclin-dependent kinase 2 (CDK2): Design, synthesis, enzymatic activities, and X-ray crystallographic analysis

Two closely related classes of oxindole-based compounds, 1H-indole-2,3-dione 3-phenylhydrazones and 3-(anilinomethylene)-1,3-dihydro-2H-indol-2-ones, were shown to potently inhibit cyclin-dependent kinase 2 (CDK2). The initial lead compound was prepared as a homologue of the 3-benzylidene-1,3-dihydro-2H-indol-2-one class of kinase inhibitor. Crystallographic analysis of the lead compound bound to CDK2 provided the basis for analogue design. A semiautomated method of ligand docking was used to select compounds for synthesis, and a number of compounds with low nanomolar inhibitory activity versus CDK2 were identified. Enzyme binding determinants for several analogues were evaluated by X-ray crystallography. Compounds in this series inhibited CDK2 with a potency ～10-fold greater than that for CDK1. Members of this class of inhibitor cause an arrest of the cell cycle and have shown potential utility in the prevention of chemotherapy-induced alopecia.

3-(cycloalkanoheteroarylidenyl)-2- indolinone protein tyrosine kinase inhibitors

The present invention relates to novel 3-(cycloalkanoheteroarylidenyl)-2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which are expected to modulate the activity of protein tyrosine kinases and therefore to be useful in the prevention and treatment of protein tyrosine kinase related cellular disorders such as cancer.