Versatile synthesis of new cytotoxic agents structurally related to hemiasterlins.
A representative series of structural analogues of the antimitotic tripeptides hemiasterlins have been synthesized. The key-step of this synthetic strategy consists of an Ag(2)O-promoted nucleophilic substitution on a common precursor, a chiral non-racemic 2-bromoacyl derivative. Simple variation of nucleophile substituents allows a rapid and stereocontrolled development of new series of derivatives. Some reported compounds showed potent biological activity as growth inhibitors of cancer cell lines and tubulin polymerization inhibitors.
Simoni
Daniele
D
Department of Pharmaceutical Sciences, University of Ferrara, Via Fossato di Mortara 17/19, 44100, Ferrara, Italy.
Lee
Ray M
RM
Durrant
David E
DE
Chi
Nai-Wen
NW
Baruchello
Riccardo
R
Rondanin
Riccardo
R
Rullo
Cinzia
C
Marchetti
Paolo
P
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats
D000970:Antineoplastic Agents; D009842:Oligopeptides; C467070:hemiasterlin