Design and synthesis of 2-cyano-3, 12-dioxoolean-1, 9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages

T Honda, BAV Rounds, GW Gribble, N Suh…

Index: Honda, Tadashi; Rounds, BarbieAnn V.; Gribble, Gordon W.; Suh, Nanjoo; Wang, Yongping; Sporn, Michael B. Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 19 p. 2711 - 2714

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Citation Number: 185

Abstract

New derivatives with electron-withdrawing substituents at the C-2 position of 3-oxoolean-1- en-28-oic acid were synthesized. Among them, 2-cyano-3, 12-dioxoolean-1, 9-dien-28-oic acid (CDDO) was 400 times more potent than previous compounds we have made as an inhibitor of production of nitric oxide induced by interferon-γ in mouse macrophages (IC50, 0.4 nM). The potency of CDDO was similar to that of dexamethasone, although CDDO ...