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ID: ALA4184275
Journal: Bioorg Med Chem Lett
Title: Synthesis of polyozellin, a prolyl oligopeptidase inhibitor, and its structural revision.
Authors: Takahashi S, Kawano T, Nakajima N, Suda Y, Usukhbayar N, Kimura KI, Koshino H.
Abstract: Polyozellin is a p-terphenyl compound which was isolated from Polyozellus multiplex, and exhibits an inhibitory activity against prolyl oligopeptidase (POP). Its structure was assigned as 1 having a p-terphenyl skeleton including a p-substituted dibenzofuran moiety by spectroscopic analyses and chemical means. This paper describes the total syntheses of the proposed structure 1 for polyozellin and its o-isomer 2, revising the structure of polyozellin to the latter. These syntheses involved a double Suzuki-Miyaura coupling using chlorophenylboronic acid as a common key building block, and Cu mediated Ullmann cyclization as key steps. The inhibitory activities of synthetic compounds against POP and cancer cells were also evaluated.
CiteXplore: 29429833