Semaxanib

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.

Semaxanib is 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. It has a role as an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor and an angiogenesis modulating agent. It is a member of pyrroles, a member of oxindoles and an olefinic compound. It derives from a 3-methyleneoxindole.|Semaxanib is a quinolone derivative with potential antineoplastic activity. Semaxanib reversibly inhibits ATP binding to the tyrosine kinase domain of vascular endothelial growth factor receptor 2 (VEGFR2), which may inhibit VEGF-stimulated endothelial cell migration and proliferation and reduce the tumor microvasculature. This agent also inhibits the phosphorylation of the stem cell factor receptor tyrosine kinase c-kit, often expressed in acute myelogenous leukemia cells.

General procedure: To a solution of indolin-2-one (compound 1) (200 mg, 1eq.) in MeOH (5 mL), piperidine (1.5 eq.), and correspondingaldehydes (2a–2k) (1.2 eq.) were added. Thereaction mixture was heated to reflux and stirred for 1–4 h, then cooled to room temperature. The mixture was filtered, and the filter cake was washed with MeOH three times, thenthe filter cake was collected and dried under vacuum toremove MeOH to give the desired compounds 3a–3k.

Adrenalone is an adrenergic agonist.

Molecular Weight:238.28
XLogP3:2.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:238.110613074
Monoisotopic Mass:238.110613074
Topological Polar Surface Area:44.9
Heavy Atom Count:18
Complexity:377
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes