Gimatecan

Base Information

• Chemical Name: Gimatecan
• CAS No.: 292618-32-7
• Molecular Formula: C₂₅H₂₅N₃O₅
• Molecular Weight: 447.491
• European Community (EC) Number: 695-730-5
• UNII: 7KKS9R192F
• DSSTox Substance ID: DTXSID0057702
• NCI Thesaurus Code: C65804
• Metabolomics Workbench ID: 149929
• ChEMBL ID: CHEMBL113051
• Mol file: 292618-32-7.mol

Synonyms:7-t-butoxyiminomethyl-camptothecin;7-t-butoxyiminomethylcamptothecin;Gimatecan;LBQ707;ST 1481;ST1481

Chemical Property of Gimatecan

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.667
• Boiling Point: 780.616 °C at 760 mmHg
• PKA: 11.20±0.20(Predicted)
• Flash Point: 425.901 °C
• PSA: 103.01000
• Density: 1.38 g/cm³
• LogP: 3.22860
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 447.17942091
• Heavy Atom Count: 33
• Complexity: 948

Purity/Quality:

98%Min ^*data from raw suppliers

Gimatecan 99.20% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC=CC=C5N=C4C3=C2)C=NOC(C)(C)C)O
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC=CC=C5N=C4C3=C2)/C=N/OC(C)(C)C)O
• Recent ClinicalTrials: A Study of Oral Gimatecan in Platinum-Resistant Epithelial Ovarian, Fallopian Tube or Peritoneal Cancer
• Recent EU Clinical Trials: 'Estudio fase II de Gimatecan (ST1481) como tratamiento de rescate en pacientes con sarcoma de partes blandas avanzado o metastático y recidivados después de un régimen de quimioterapia basado en antraciclinas / ifosfamida'

Technology Process of Gimatecan

There total 4 articles about Gimatecan 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: 93.0%

7-formyl-camptothecin + O-(tert-butyl)hydroxylamine hydrochloride (39684-28-1) → gimatecan (292618-32-7)

Guidance literature:

With sodium hydroxide; In ethanol; for 2h; Product distribution / selectivity; Reflux; Darkness;

Reference yield: 87.0%

O-(tert-butyl)hydroxylamine hydrochloride (39684-28-1) + 7-(dimethoxymethyl)camptothecin (84017-99-2) → gimatecan (292618-32-7)

Guidance literature:

In ethanol; for 4h; Product distribution / selectivity; Reflux; Darkness;

Reference yield:

anti-7-tert-butoxyiminomethylcamptothecin → gimatecan (292618-32-7)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; at 20 ℃; for 1h; irradiation with a 125 W Hg high pressure U_.V_. lamp;

upstream raw materials:

O-(tert-butyl)hydroxylamine

(20S)-camptothecin-7-carboxaldehyde

O-(tert-butyl)hydroxylamine hydrochloride

7-(dimethoxymethyl)camptothecin

Downstream raw materials:

(E)-7-tert-butoxyiminomethyl-20-O-(2-methoxyphenylglycyl)succinyl-camptothecin

Refernces

• 1、 -. "STEREOSELECTIVE PROCESS AND CRYSTALLINE FORMS OF A CAMPTOTHECIN". Page/Page column 4. . Retrieved 2009/10/01.