Abstract
Kynapcin-12 is a prolyl oligopeptidase (POP) inhibitor isolated from Polyozellus multiplex, and its structure was assigned as 1 having a p-hydroquinone moiety by spectroscopic analyses and chemical means. This Letter describes the total syntheses of the proposed structure 1 for kynapcin-12 and 2',3'-diacetoxy-1,5',6',4″-tetrahydroxy-p-terphenyl 2 isolated from Boletopsis grisea, revising the structure of kynapcin-12 to the latter. These syntheses involved double Suzuki-Miyaura coupling, CAN oxidation, and LTA oxidation as key steps. The inhibitory activities of synthetic compounds against POP and cancer cells were also evaluated.
Keywords:
Kynapcin-12; Prolyl oligopeptidase inhibitor; p-Terphenyl.
Copyright © 2014 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Agaricales / chemistry
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / pharmacology*
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Cell Proliferation / drug effects
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Dose-Response Relationship, Drug
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Drug Screening Assays, Antitumor
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / isolation & purification
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Enzyme Inhibitors / pharmacology*
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HL-60 Cells
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Humans
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Molecular Structure
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Prolyl Oligopeptidases
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Serine Endopeptidases / metabolism*
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Structure-Activity Relationship
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Terphenyl Compounds / chemistry
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Terphenyl Compounds / isolation & purification
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Terphenyl Compounds / pharmacology*
Substances
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Antineoplastic Agents
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Enzyme Inhibitors
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Terphenyl Compounds
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kynapcin 12
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Serine Endopeptidases
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PREPL protein, human
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Prolyl Oligopeptidases