| Identification | Back Directory | [Name]
3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon | [CAS]
194413-58-6 | [Synonyms]
TSU 16
CS-1141
17022(Z)
Semaxanib
(Z)-SU 5416
(Z)-Semaxinib
Unii-71ia9S35aj
SeMaxanib,SU5416
Semaxanib
(Z)-SU 5416
3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon
3-((2,4-DIMETHYLPYRROL-5-YL)METHYLIDENYL)-2-INDOLONONE
3-((Z)-(3,5-Dimethylpyrrol-2-yl)methylene)-2-indolinone
3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon USP/EP/BP
(3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one
3-(1-(3,5-Dimethyl-1H-pyrrol-2-yl)meth-(Z)-ylidene)-2-oxo-2,3-dihydroindole
2H-Indol-2-one, 3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-1,3-dihydro-, (Z)-
2H-Indol-2-one, 3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-1,3-dihydro-, (3Z)-
3-[(3,5-Dimethyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-2H-indol-2-one Semaxanib (SU5416) TSU 16 | [Molecular Formula]
C15H14N2O | [MDL Number]
MFCD09763655 | [MOL File]
194413-58-6.mol | [Molecular Weight]
238.28 |
| Chemical Properties | Back Directory | [Melting point ]
220-222℃ | [density ]
1.256 | [storage temp. ]
Sealed in dry,2-8°C | [InChI]
InChI=1S/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- | [InChIKey]
WUWDLXZGHZSWQZ-WQLSENKSSA-N | [SMILES]
N1C2=C(C=CC=C2)/C(=C/C2=C(C)C=C(C)N2)/C1=O |
| Hazard Information | Back Directory | [Uses]
Adrenalone is an adrenergic agonist. | [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. | [Synthesis]
GENERAL METHOD: 2-Indolone (200 mg, 1 eq.) was dissolved in methanol (5 mL) and piperidine (1.5 eq.) and 3,5-dimethyl-2-pyrrolecarboxaldehyde (1.2 eq.) were added sequentially. The reaction mixture was heated to reflux with continuous stirring for 1 to 4 hours. After completion of the reaction, it was cooled to room temperature. The reaction mixture was filtered and the resulting solid was washed three times with methanol. The solid product was collected and dried under vacuum to remove residual methanol to give the final target product (Z)-3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)dihydroindol-2-one. | [References]
[1] Journal of Antibiotics, 2018, vol. 71, # 10, p. 887 - 897
[2] Tetrahedron, 2009, vol. 65, # 25, p. 4894 - 4903
[3] ChemMedChem, 2016, vol. 11, # 1, p. 72 - 80
[4] Journal of Medicinal Chemistry, 1998, vol. 41, # 14, p. 2588 - 2603
[5] Synthetic Communications, 2008, vol. 38, # 17, p. 3017 - 3022 |
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