Synthesis of antitrypanosomal 1,2-dioxane derivatives based on a natural product scaffold
Author(s)
Holla, Harish
Labaied, Mehdi
Ngoc, Pham
Jenkins, Ian D
Stuart, Kenneth
Quinn, Ronald J
Year published
2011
Metadata
Show full item recordAbstract
A short practical synthesis of a new natural product based scaffold (6), based on antitrypanosomal and antimalarial compounds isolated from different Plakortis species is described. The scaffold contains a peroxide unit that is surprisingly stable to chemical manipulation elsewhere in the molecule, enabling it to be elaborated into a small library of derivatives. It is stable to ozonolysis, reductive work-up with dimethylsulfide and the Wittig reaction with stabilized phosphorus ylides. The scaffold along with its Wittig analogues has displayed low to sub-micro molar (0.2-3.3 lM) antitrypanosomal activity.A short practical synthesis of a new natural product based scaffold (6), based on antitrypanosomal and antimalarial compounds isolated from different Plakortis species is described. The scaffold contains a peroxide unit that is surprisingly stable to chemical manipulation elsewhere in the molecule, enabling it to be elaborated into a small library of derivatives. It is stable to ozonolysis, reductive work-up with dimethylsulfide and the Wittig reaction with stabilized phosphorus ylides. The scaffold along with its Wittig analogues has displayed low to sub-micro molar (0.2-3.3 lM) antitrypanosomal activity.
View less >
View less >
Journal Title
Bioorganic & Medicinal Chemistry Letters
Volume
21
Issue
16
Subject
Medicinal and biomolecular chemistry
Biologically active molecules
Medicinal and biomolecular chemistry not elsewhere classified
Organic chemistry
Organic chemical synthesis
Pharmacology and pharmaceutical sciences