Diflomotecan

Base Information

• Chemical Name: Diflomotecan
• CAS No.: 220997-97-7
• Molecular Formula: C₂₁H₁₆F₂N₂O₄
• Molecular Weight: 398.366
• UNII: QKT1LC4J1P
• DSSTox Substance ID: DTXSID201026358
• Nikkaji Number: J1.552.392A,J1.372.376A
• Wikipedia: Diflomotecan
• NCI Thesaurus Code: C90824
• ChEMBL ID: CHEMBL306280
• Mol file: 220997-97-7.mol

Synonyms:BN 80915;BN-80915;BN80915;diflomotecan

Chemical Property of Diflomotecan

Chemical Property:

• Boiling Point: 784.2°Cat760mmHg
• Flash Point: 428.1°C
• PSA: 81.42000
• Density: 1.56g/cm³
• LogP: 2.74790
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 398.10781332
• Heavy Atom Count: 29
• Complexity: 828

Purity/Quality:

99% ^*data from raw suppliers

Difloomotecan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1(CC(=O)OCC2=C1C=C3C4=C(CN3C2=O)C=C5C=C(C(=CC5=N4)F)F)O
• Isomeric SMILES: CC[C@]1(CC(=O)OCC2=C1C=C3C4=C(CN3C2=O)C=C5C=C(C(=CC5=N4)F)F)O
• Recent ClinicalTrials: Diflomotecan (BN80915) Administered Once Every 3 Weeks in Treating Patients With Sensitive Small Cell Lung Cancer (SCLC)
• Uses: Difloomotecan is a homocamptothecin that targets DNA topoisomerase I. Difloomotecan is used in cancer therapy.

Technology Process of Diflomotecan

There total 40 articles about Diflomotecan 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: 61.0%

(+)-8-(2-chloro-6,7-difluoro-3-quinolinemethanol)-5-ethyl-5-hydroxy-1,3,4,5,8,9-hexahydrooxepino[3,4-c]pyridine-3,9-dione → (+)-5-ethyl-9,10-difluoro-5-hydroxy-4,5,13,15-tetrahydro-1H,3H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione (220997-97-7)

Guidance literature:

With tetrabutylammomium bromide; potassium acetate; triphenylphosphine; palladium diacetate; In acetonitrile; for 22h; Heating / reflux;

Reference yield: 48.0%

8-<(2-chloro-6,7-difluoro-3-quinolyl)methyl>-5-ethyl-1,4,5,8tetrahydro-5-hydroxyoxepino<3,4-c>pyridine-3,9-dione (209909-04-6) → 5-ethyl-9,10-difluoro-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione (186668-70-2,220997-97-7)

Guidance literature:

With palladium diacetate; sodium acetate; tetra(n-tert-butyl)ammonium bromide; triphenylphosphine; In acetonitrile; for 36h; Heating;

DOI:10.1021/jm980400l

Reference yield:

→ 5-ethyl-9,10-difluoro-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione (186668-70-2,220997-97-7) + 3,4-difluoroaniline (3863-11-4)

Guidance literature:

upstream raw materials:

8-<(2-chloro-6,7-difluoro-3-quinolyl)methyl>-5-ethyl-1,4,5,8tetrahydro-5-hydroxyoxepino<3,4-c>pyridine-3,9-dione

1-(2-chloropyridin-4-yl)propan-1-one

4-(2-ethyl[1,3]dioxolan-2-yl)-2-methoxypyridine

2-chloro-6,7-difluoro-3-quinoline-3-carbaldehyde

Refernces

• 1、 -. "New analogues of camptothecin, their use as medicaments and the pharmaceutical compositions containing them". . . Retrieved 2008/06/13.
• 2、 -. "Comptothecin analogues, preparation methods therefor, use thereof as drugs, and pharmaceutical compositions containing said analogues". Example 81. . Retrieved 2008/06/13.