[Synthesis and spectral characterization of 10-hydroxycamptothecin].
10-hydroxycamptothecin was synthesized from camptothecin through oxidation and photo-activation. Grouping and optimizing the reaction conditions were as follows: in the oxidation condition: the reaction time 4 h, the reaction temperature 75 degrees C, the amount of H2O2 48 mL(w(H2O2) = 30%), the amount of HAc 350 mL(based on 0.01 mol CPT); in the photochemical reaction: the solvents V(1,4-dioxane): V(acetonitrile): V(H2O) = 6:2:1, bronsted acid catalyst 98% H2SO4. Purified by silica gel column, the total yield of HCPT is 49.9%, with 99.5% purity, m.p. 272-273 degrees C. The molecular structure of the title compound has been characterized by elemental analysis (EA), mass spectroscopy (MS), infrared spectrscopy(IR), and ID and 2D nuclear magnetic resonance spectrometry (NMR), and the main infrared absorption peaks and nuclear magnetic spectral bands of this conpound were assigned. The mass spectral fragmentations of the product's important fragment ions were elucidated. The result provides useful information for preparing the new derivatives of camptothecin.
College of Materials Science and Technology, Beijing University of Chemical Technology, Beijing 100029, China.
Chun-yan
CY
Xu
Ming-zhi
MZ
Huang
Chuan-xin
CX
Xue
D002166:Camptothecin / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry; D013058:Mass Spectrometry; D008958:Models, Molecular; D015394:Molecular Structure; D013057:Spectrum Analysis
C028098:10-hydroxycamptothecin; D002166:Camptothecin