Selective phenolic acylation of 10-hydroxycamptothecin using poly (ethylene glycol) carboxylic acid.
Selective acylation of the phenolic hydroxyl group of 10-hydroxycamptothecin has been accomplished using phenyl dichlorophosphate. Additional modification of the 10-OH as an ether permits a 20-acyl derivative to be synthesized. This result along with data from a 6-hydroxyquinoline model strongly suggests that powerful intermolecular hydrogen bonding exists in the parent molecule.
Greenwald
Richard B
RB
Enzon, Inc., 20 Kingsbridge Road, Piscataway, NJ 08854, USA. richard.greewald@enzon.com
Choe
Yun H
YH
Wu
Dechun
D
D000215:Acylation; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D002166:Camptothecin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D002264:Carboxylic Acids / Q000737:chemistry; D006860:Hydrogen Bonding; D006912:Hydroxyquinolines / Q000737:chemistry; D007202:Indicators and Reagents; D007941:Leukemia P388 / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D009369:Neoplasms / Q000188:drug therapy / Q000473:pathology; D011092:Polyethylene Glycols / Q000737:chemistry; D051381:Rats; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D002264:Carboxylic Acids; D006912:Hydroxyquinolines; D007202:Indicators and Reagents; D011092:Polyethylene Glycols; C071287:6-hydroxyquinoline; C028098:10-hydroxycamptothecin; D002166:Camptothecin