Literature DB >> 9873608

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 Honda1, B V Rounds, G W Gribble, N Suh, Y Wang, M B Sporn.   

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-gamma in mouse macrophages (IC50, 0.4 nM). The potency of CDDO was similar to that of dexamethasone, although CDDO does not act through the glucocorticoid receptor.

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Year:  1998        PMID： 9873608     DOI： 10.1016/s0960-894x(98)00479-x

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  66 in total

1.  CDDO-methyl ester delays breast cancer development in BRCA1-mutated mice.

Authors:  Eun-Hee Kim; Chuxia Deng; Michael B Sporn; Darlene B Royce; Renee Risingsong; Charlotte R Williams; Karen T Liby
Journal:  Cancer Prev Res (Phila)       Date:  2011-09-20

2.  The triterpenoid CDDO-Me delays murine acute graft-versus-host disease with the preservation of graft-versus-tumor effects after allogeneic bone marrow transplantation.

Authors:  Minghui Li; Kai Sun; Doug Redelman; Lisbeth A Welniak; William J Murphy
Journal:  Biol Blood Marrow Transplant       Date:  2010-03-23       Impact factor: 5.742

3.  CDDO-Im protects from acetaminophen hepatotoxicity through induction of Nrf2-dependent genes.

Authors:  Scott A Reisman; David B Buckley; Yuji Tanaka; Curtis D Klaassen
Journal:  Toxicol Appl Pharmacol       Date:  2009-01-20       Impact factor: 4.219

4.  AN EFFICIENT SYNTHESIS OF TRICYCLIC COMPOUNDS, (+/-)-(4abeta8abeta10aalpha)-1,2,3,4,4a,6,7,8,8a,9,10,10a-DODECAHYDRO-1,1,4a-TRIMETHYL-2-OXOPHENANTHRENE-8a-CARBOXYLIC ACID, ITS METHYL ESTER, AND (+/-)-(4abeta,8abeta10aalpha)-3,4,4a,6,7,8,8a,9,10,10a-DECAHYDRO-8a-HYDROXYMETHYL-1,1,4a-TRIMETHYLPHENANTHREN-2(1H)-ONE.

Authors:  Tadashi Honda; Yukiko Honda; Hidenori Yoshizawa; Gordon W Gribble
Journal:  Org Prep Proced Int       Date:  2005-12       Impact factor: 1.628

5.  Chemical modifications of natural triterpenes - glycyrrhetinic and boswellic acids: evaluation of their biological activity.

Authors:  G S R Subba Rao; Paturu Kondaiah; Sanjay K Singh; Palaniyandi Ravanan; Michael B Sporn
Journal:  Tetrahedron       Date:  2008-12-15       Impact factor: 2.457

6.  The synthetic triterpenoid, CDDO-Me, modulates the proinflammatory response to in vivo lipopolysaccharide challenge.

Authors:  Jeffery J Auletta; Jennifer L Alabran; Byung-Gyu Kim; Colin J Meyer; John J Letterio
Journal:  J Interferon Cytokine Res       Date:  2010-07       Impact factor: 2.607

Review 7.  Combating oxidative stress in diabetic complications with Nrf2 activators: how much is too much?

Authors:  Sih Min Tan; Judy B de Haan
Journal:  Redox Rep       Date:  2014-02-21       Impact factor: 4.412

8.  Bardoxolone brings Nrf2-based therapies to light.

Authors:  Donna D Zhang
Journal:  Antioxid Redox Signal       Date:  2013-01-11       Impact factor: 8.401

Review 9.  Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents.

Authors:  Reen-Yen Kuo; Keduo Qian; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  Nat Prod Rep       Date:  2009-08-13       Impact factor: 13.423

10.  Oleanane triterpenoid CDDO-Me inhibits growth and induces apoptosis in prostate cancer cells by independently targeting pro-survival Akt and mTOR.

Authors:  Dorrah Deeb; Xiaohua Gao; Hao Jiang; Scott A Dulchavsky; Subhash C Gautam
Journal:  Prostate       Date:  2009-06-01       Impact factor: 4.104
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