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

Description

3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon is an oxindole compound characterized by the presence of a 3-methyleneoxindole group, where one of the hydrogens of the methylene group is replaced by a 3,5-dimethylpyrrol-2-yl group. This unique molecular structure endows it with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon is used as an adrenergic agonist for treating conditions related to the sympathetic nervous system, such as asthma, allergies, and cardiovascular disorders. Its molecular structure allows it to interact with adrenergic receptors, modulating the body's response to stress and promoting bronchodilation and vasoconstriction.
Used in Oncology Research:
In the field of oncology, 3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon is used as a potent and selective VEGFR (Flk-1/KDR) inhibitor. This application is crucial for targeting and inhibiting the activity of vascular endothelial growth factor receptors, which play a significant role in tumor angiogenesis and growth. By inhibiting VEGFR, this compound can potentially limit the formation of new blood vessels that supply nutrients and oxygen to tumors, thereby slowing down their growth and spread.
Overall, 3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon is a versatile compound with potential applications in both the pharmaceutical industry and oncology research, making it a valuable asset for the development of new therapeutic agents and treatment strategies.

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

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

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.