194413-58-6

Basic information

• Product Name: 3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon
• Synonyms: 2H-Indol-2-one, 3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-1,3-dihydro-, (Z)-;3-((Z)-(3,5-Dimethylpyrrol-2-yl)methylene)-2-indolinone;3-(1-(3,5-Dimethyl-1H-pyrrol-2-yl)meth-(Z)-ylidene)-2-oxo-2,3-dihydroindole;Semaxanib;Unii-71ia9S35aj;(Z)-SU 5416;TSU 16;SeMaxanib,SU5416
• CAS NO: 194413-58-6
• Molecular Formula: C₁₅H₁₄N₂O
• Molecular Weight: 238.289
• Product Categories: Inhibitors
• Mol File: 194413-58-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 220-222℃
• Boiling Point: 481.4°Cat760mmHg
• Flash Point: 244.9°C
• Appearance: /
• Density: 1.256
• Vapor Pressure: 2E-09mmHg at 25°C
• Refractive Index: 1.683
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon(194413-58-6)
• EPA Substance Registry System: 3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon(194413-58-6)

Safety Data

• Hazardous Substances Data: 194413-58-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 194413-58-6 differently. You can refer to the following data:
1. Adrenalone is an adrenergic agonist.
2. Semaxanib is a potent and selective VEGFR(Flk-1/KDR) inhibitor.

Definition

ChEBI: An oxindole that is 3-methyleneoxindole in which one of the hydrogens of the methylene group is replaced by a 3,5-dimethylpyrrol-2-yl group.

InChI:InChI=1/C15H14N2O/c1-9-7-10(2)16-14(9)8-12-11-5-3-4-6-13(11)17-15(12)18/h3-8,16H,1-2H3,(H,17,18)/b12-8-

Upstream product

• 2199-58-8 3,5-dimethylpyrrole-2-carbaldehyde 
• 59-48-3 2-oxoindole 
• 110-89-4 piperidine 
• 1243657-66-0 1,3-diethyl 2-(2-bromophenylamino)-2-oxoethylphosphonate 
• 152302-94-8 N-(2-Iodophenyl)-α-(diethoxyphosphinyl)acetamide 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 194413-57-5 semaxanib 

Downstream Products

• 375824-74-1 benzyl 2-{(3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2-oxo-2,3-dihydro-1H-indol-1-yl}-2-oxoethylcarbamate 

Relevant articles and documents

Photoinduced Isomerization and Hepatoxicities of Semaxanib, Sunitinib and Related 3-Substituted Indolin-2-ones

3-Substituted indolin-2-ones are an important class of compounds that display a wide range of biological activities. Sunitinib is an orally available multiple tyrosine kinase inhibitor that has been approved by the US Food and Drug Administration (FDA) for the treatment of renal cell cancer. Sunitinib and a related compound, semaxanib, exist as thermodynamically stable Z isomers, which photoisomerize to E isomers in solution. In this study, 17 3-substituted indolin-2-ones were synthesized, and the kinetics of their photoisomerization were studied by 1H NMR spectroscopy. The rate constants for photoisomerization ranged from 0.009 to 0.048 h-1. Selected compounds were tested for cytotoxicity in the TAMH liver cell line. E/Z mixtures of four compounds were also assessed for toxicity in the TAMH and HepG2 cell lines. In some cases, the stereochemically pure drug was more toxic than the E/Z mixtures, but a general statement cannot be made. Our studies show that each stereoisomer could contribute differently to toxicity, suggesting that stereochemical purity issues that could arise from isomerization cannot be ignored.

Facile synthesis of various nitro-substituted derivatives of Semaxinib (SU5416)

The synthesis of novel nitro-substituted derivatives of the tyrosine kinase inhibitor Semaxinib (SU5416) is described. The reaction of various substituted oxindoles with 3,5-dimethylpyrrol-2-carbaldehyde derivatives under Knoevenagel conditions gave an array of nitro-substituted derivatives of Semaxinib (SU5416) in high yields of 72-87%. Copyright Taylor & Francis Group, LLC.

Tandem Horner-Wadsworth-Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: The synthesis of Semaxanib and GW441756

A tandem sequence involving Horner-Wadsworth-Emmons (HWE) olefination followed by a palladium-catalysed intramolecular Heck reaction has been developed to provide rapid access to 3-alkenyl-oxindoles from α-halo-anilides. This one-pot microwave accelerated process proceeds with catalytic palladium(II) acetate or tetrakis(triphenylphosphine)palladium, and has been used to prepare a range of adducts derived from aromatic, heteroaromatic and aliphatic aldehydes. The procedures can be used to prepare N-unprotected oxindoles directly and the applicability of the process has been established by carrying out one-pot syntheses of Semaxanib, an angiogenesis signalling inhibitor, and GW441756, an aza-oxindole Trk A inhibitor.