Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent

Tadashi Honda, Albena T. Dinkova-Kostova, Emilie David, Eric M. Padegimas, Chitra Sundararajan, Melean Visnick, Ron Bumeister, W. Christian Wigley

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    17 Citations (Scopus)

    Abstract

    To explore more potent N-acylimidazole analogues of CDDO than CDDO-Im, which is one of the most potent compounds in several widely used bioassays related to protection against inflammation and carcinogenesis; we have synthesized and evaluated five new N-acyl(acetylenic) imidazole analogues. Among them, 4-ethynylimidazole 4 is nearly equivalent to CDDO-Im in potency in these bioassays. Remarkably, the solid form of 4 is more stable than that of CDDO-Im. These findings suggest that 4 is a very promising anti-inflammatory and cytoprotective agent and its further preclinical evaluation is warranted. (C) 2011 Elsevier Ltd. All rights reserved.

    Original languageEnglish
    Pages (from-to)2188-2191
    Number of pages4
    JournalBioorganic & Medicinal Chemistry Letters
    Volume21
    Issue number8
    DOIs
    Publication statusPublished - 15 Apr 2011

    Keywords

    • Triterpene
    • Oleanolic acid
    • Acetylenicimidazole
    • Inhibitors of nitric oxide production
    • Inducers of heme oxygenase-1
    • NQO1
    • NITRIC-OXIDE PRODUCTION
    • URSANE TRITERPENOIDS
    • MOUSE MACROPHAGES
    • PROTECTION
    • INHIBITORS
    • AFLATOXIN
    • PATHWAYS
    • OLEANANE
    • RING

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