Semaxanib

Base Information

• Chemical Name: Semaxanib
• CAS No.: 194413-58-6
• Molecular Formula: C15H14 N2 O
• Molecular Weight: 238.28
• European Community (EC) Number: 621-120-5
• NSC Number: 696819
• UNII: 71IA9S35AJ
• DSSTox Substance ID: DTXSID801025708
• Nikkaji Number: J1.051.859H,J2.299.233C
• Wikipedia: Semaxanib
• Wikidata: Q7449140
• NCI Thesaurus Code: C1831
• RXCUI: 805452
• Pharos Ligand ID: 1VWBTP8XJNZZ
• Metabolomics Workbench ID: 149777
• ChEMBL ID: CHEMBL276711
• Mol file: 194413-58-6.mol

Synonyms:3-(2,4-dimethylpyrrol-5-yl)methylidene-indolin-2-one;Semaxinib;SU 5416;SU-5416;SU5416;Sugen 5416

Chemical Property of Semaxanib

Chemical Property:

• Vapor Pressure: 2E-09mmHg at 25°C
• Melting Point: 220-222℃
• Boiling Point: 481.4°Cat760mmHg
• Flash Point: 244.9°C
• PSA: 44.89000
• Density: 1.256g/cm³
• LogP: 3.26220
• Storage Temp.: 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 238.110613074
• Heavy Atom Count: 18
• Complexity: 377

Purity/Quality:

98%,99%, ^*data from raw suppliers

Semaxanib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(N1)C=C2C3=CC=CC=C3NC2=O)C
• Isomeric SMILES: CC1=CC(=C(N1)/C=C\2/C3=CC=CC=C3NC2=O)C
• Recent ClinicalTrials: SU5416 in Treating Patients With Recurrent Astrocytoma or Mixed Glioma That Has Not Responded to Radiation Therapy
• Recent EU Clinical Trials: A multicentre, randomized, open-label study of romiplostim plus dexamethasone vs dexamethasone in patients with newly diagnosed primary immune thrombocytopenia
• Uses: Adrenalone is an adrenergic agonist. Semaxanib is a potent and selective VEGFR(Flk-1/KDR) inhibitor.

Technology Process of Semaxanib

There total 16 articles about Semaxanib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

3,5-dimethylpyrrole-2-carbaldehyde (2199-58-8) + 2-oxoindole (59-48-3) → semaxanib (194413-58-6)

Guidance literature:

With piperidine; In methanol; Reflux;

DOI:10.1038/s41429-018-0076-5

Reference yield: 84.0%

((2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl (Z)-3-(3,5-dimethyl-1H-pyrrol-2-yl)-2-(2-nitrophenyl)acrylate → (Z)-3-(3,5-dimethyl-1H-pyrrol-2-ylmethylene)-1-hydroxy-1,3-dihydro-indol-2-one + semaxanib (194413-58-6)

Guidance literature:

With iron; acetic acid; In ethanol; water; at 20 ℃; for 1h; Reagent/catalyst; Sonication;

DOI:10.1016/j.bmcl.2019.03.015

Reference yield: 80.0%

(Z)-N-(4-(bis(2-chloroethyl)amino)phenyl)-3-(3,5-dimethyl-1H-pyrrol-2-yl)-2-(2-nitrophenyl)acrylamide → (Z)-3-(3,5-dimethyl-1H-pyrrol-2-ylmethylene)-1-hydroxy-1,3-dihydro-indol-2-one + semaxanib (194413-58-6)

Guidance literature:

With iron; acetic acid; In ethanol; water; at 20 ℃; for 1h; Reagent/catalyst; Sonication;

DOI:10.1016/j.bmcl.2019.03.015

upstream raw materials:

3,5-dimethylpyrrole-2-carbaldehyde

2-oxoindole

piperidine

1,3-diethyl 2-(2-bromophenylamino)-2-oxoethylphosphonate

Downstream raw materials:

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

Refernces

• 1、 Sansom, Geraud N.,Kirk, Nicholas S.,Guise, Christopher P.,Anderson, Robert F.,Smaill, Jeff B.,Patterson, Adam V.,Kelso, Michael J.. "Prototyping kinase inhibitor-cytotoxin anticancer mutual prodrugs activated by tumour hypoxia: A chemical proof of concept study". . p. 1215 - 1219. Retrieved 2019.
• 2、 Zhou, Yuanzheng,Ju, Yuan,Yang, Yang,Sang, Zitai,Wang, Zhenling,He, Gu,Yang, Tao,Luo, Youfu. "Discovery of hybrids of indolin-2-one and nitroimidazole as potent inhibitors against drug-resistant bacteria". . p. 887 - 897. Retrieved 2018/07/13.