title: The solvolysis of topotecan in alcohols and acetic anhydride.
abstract: Six derivatives of 10-hydroxycamptothecin were prepared via solvolysis of topotecan in corresponding alcohols and acetic anhydride. We attributed the specific reactivity of topotecan to the internal hydrogen-bonding between 10-hydroxy and the nitrogen atom in position 9. As a result the reaction underwent through an intermediate ortho-quionomethlide species to reach equilibrium. Bioactivity screening data showed all products could potentially inhibit the proliferation of several cancer cell lines in vitro and a bigger size group in 9-position would be favorable for the anti-tumor activities observably.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China.
authors.forename: Jiajun
authors.initials: J
authors.lastname: Li
authors.forename: Guolin
authors.initials: G
authors.lastname: Wang
authors.forename: Mengjie
authors.initials: M
authors.lastname: Dong
authors.forename: Qian
authors.initials: Q
authors.lastname: Zhang
mesh_terms: D000089:Acetic Anhydrides / Q000737:chemistry*; D000438:Alcohols / Q000737:chemistry*; D006860:Hydrogen Bonding; D012997:Solvents / Q000737:chemistry*; D019772:Topotecan / Q000737:chemistry*
chemical_list: D000089:Acetic Anhydrides; D000438:Alcohols; D012997:Solvents; C031800:acetic anhydride; D019772:Topotecan