Synthesis and biological activity of analogues of ptilomycalin A

Autor: Shoshana Loya, Patrick J. Murphy, Amnon Hizi, Andrew Howard-Jones, Simon J. Coles, Gregory P. Black, Christopher G. Moore, Michael B. Hursthouse, Walshe Nigel Derek Arthur, Nigel K. Smith, Alan T McGown
Rok vydání: 2001
Předmět:
Zdroj: Tetrahedron Letters. 42:3377-3381
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00400-2
Popis: Benzo-fused model compounds 21a and 21b, resembling in structure the marine metabolite ptilomycalin A, were prepared and were shown to display significant activity against a series of cancer cell lines and to also possess a significant activity against the DNA polymerase activity of the reverse transcriptase of human immunodeficiency virus type 1 (HIV-1 RT). © 2001 Elsevier Science Ltd. All rights reserved. Ptilomycalin A 1 and related natural products have been the subject of considerable synthetic interest owing to their high levels of diverse biological activity. This includes cytotoxicity towards several cancer cell lines as well as antifungal and antiviral activities. 1 Despite this range of activity, only one report of the synthesis of a structural analogue of ptilomycalin A has been reported, by Hart and Grillot, which detailed the prepa- ration of the racemic bicyclic guanidine 2 2 (Scheme 1). As can be seen, ptilomycalin A can be considered as four separate components, a guanidine-containing poly- cyclic core, an ester linkage to an -hydroxyacid spacer unit and a terminal spermidine residue. In common
Databáze: OpenAIRE