Synthesis and biological evaluation of tamandarin B analogues.
[structure: see text]. The synthesis of two tamandarin B analogues in which the N,O-Me2Tyr5 unit was replaced by N-Me-phenylalanine (N-MePhe5) and (S)-2-(methylamino)-3-(naphthalen-2-yl)propanoic acid (N-MeNaphth5) is described. The choice of the macrocyclization site was crucial to achieve satisfactory macrolactamization. Coupling between norstatine (Nst1) and threonine (Thr6) afforded only a 15% yield, while lactamization between proline (Pro4) and the aromatic moiety could be achieved in 65% yield.
Adrio
Javier
J
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Cuevas
Carmen
C
Manzanares
Ignacio
I
Joullié
Madeleine M
MM
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004317:Doxorubicin / Q000494:pharmacology; D019008:Drug Resistance, Neoplasm / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D010456:Peptides, Cyclic; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D047630:Depsipeptides; D010456:Peptides, Cyclic; C433835:tamandarin B; D004317:Doxorubicin; C098980:plitidepsin