The amido-pentadienoate-functionality of the rakicidins is a thiol reactive electrophile--development of a general synthetic strategy.

Autor: Clement LL; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark. thpou@chem.au.dk., Tsakos M, Schaffert ES, Scavenius C, Enghild JJ, Poulsen TB
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2015 Aug 11; Vol. 51 (62), pp. 12427-30.
DOI: 10.1039/c5cc04500b
Abstrakt: We demonstrate that a unique class-defining functionality (mc-APD) found in macrocyclic natural products with potent anti-cancer activity, imparts these compounds with electrophilic reactivity. The mc-APD group represents an interesting structural hybrid between canonical biologically relevant Michael-acceptors. Further, a novel thiol-elimination method for preparation of the mc-APD group is outlined.
Databáze: MEDLINE