Literature DB >> 17367124

Novel tricyclic compounds having acetylene groups at C-8a and cyano enones in rings A and C: highly potent anti-inflammatory and cytoprotective agents.

Tadashi Honda1, Chitra Sundararajan, Hidenori Yoshizawa, Xiaobo Su, Yukiko Honda, Karen T Liby, Michael B Sporn, Gordon W Gribble.   

Abstract

Novel C-8a functionalized tricyclic compounds having cyano enones in rings A and C have been synthesized and biologically evaluated. Among them, compounds with acetylene groups at C-8a show extremely high potency in in vitro and in vivo bioassays for anti-inflammatory and cytoprotective activities. Both in vitro and in vivo potencies are markedly higher than those of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO), which is being evaluated as an anticancer drug in phase I clinical trials.

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Year:  2007        PMID： 17367124      PMCID： PMC2522370          DOI： 10.1021/jm070141c

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  11 in total

1.  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

2.  A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production.

Authors:  Tadashi Honda; Yukiko Honda; Frank G Favaloro; Gordon W Gribble; Nanjoo Suh; Andrew E Place; Mara H Rendi; Michael B Sporn
Journal:  Bioorg Med Chem Lett       Date:  2002-04-08       Impact factor: 2.823

3.  Design and synthesis of tricyclic compounds with enone functionalities in rings A and C: a novel class of highly active inhibitors of nitric oxide production in mouse macrophages.

Authors:  Frank G Favaloro; Tadashi Honda; Yukiko Honda; Gordon W Gribble; Nanjoo Suh; Renee Risingsong; Michael B Sporn
Journal:  J Med Chem       Date:  2002-10-24       Impact factor: 7.446

4.  Novel synthetic oleanane and ursane triterpenoids with various enone functionalities in ring A as inhibitors of nitric oxide production in mouse macrophages.

Authors:  T Honda; G W Gribble; N Suh; H J Finlay; B V Rounds; L Bore; F G Favaloro; Y Wang; M B Sporn
Journal:  J Med Chem       Date:  2000-05-04       Impact factor: 7.446

Review 5.  Heme oxygenase-1/carbon monoxide: from basic science to therapeutic applications.

Authors:  Stefan W Ryter; Jawed Alam; Augustine M K Choi
Journal:  Physiol Rev       Date:  2006-04       Impact factor: 37.312

6.  Synthetic oleanane and ursane triterpenoids with modified rings A and C: a series of highly active inhibitors of nitric oxide production in mouse macrophages.

Authors:  T Honda; B V Rounds; L Bore; H J Finlay; F G Favaloro; N Suh; Y Wang; M B Sporn; G W Gribble
Journal:  J Med Chem       Date:  2000-11-02       Impact factor: 7.446

7.  Synthetic Studies on Quassinoids: Total Synthesis and Biological Evaluation of (+)-Des-D-chaparrinone.

Authors:  Paul A. Grieco; Jason D. Speake
Journal:  J Org Chem       Date:  1998-08-21       Impact factor: 4.354

8.  Efficient synthesis of (-)- and (+)-tricyclic compounds with enone functionalities in rings A and C. A novel class of orally active anti-inflammatory and cancer chemopreventive agents.

Authors:  Tadashi Honda; Frank G Favaloro; Tomasz Janosik; Yukiko Honda; Nanjoo Suh; Michael B Sporn; Gordon W Gribble
Journal:  Org Biomol Chem       Date:  2003-10-31       Impact factor: 3.876

9.  The novel synthetic triterpenoid, CDDO-imidazolide, inhibits inflammatory response and tumor growth in vivo.

Authors:  Andrew E Place; Nanjoo Suh; Charlotte R Williams; Renee Risingsong; Tadashi Honda; Yukiko Honda; Gordon W Gribble; Lisa M Leesnitzer; Julie B Stimmel; Timothy M Willson; Evan Rosen; Michael B Sporn
Journal:  Clin Cancer Res       Date:  2003-07       Impact factor: 12.531

10.  A novel synthetic oleanane triterpenoid, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, with potent differentiating, antiproliferative, and anti-inflammatory activity.

Authors:  N Suh; Y Wang; T Honda; G W Gribble; E Dmitrovsky; W F Hickey; R A Maue; A E Place; D M Porter; M J Spinella; C R Williams; G Wu; A J Dannenberg; K C Flanders; J J Letterio; D J Mangelsdorf; C F Nathan; L Nguyen; W W Porter; R F Ren; A B Roberts; N S Roche; K Subbaramaiah; M B Sporn
Journal:  Cancer Res       Date:  1999-01-15       Impact factor: 12.701
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  9 in total

1.  An exceptionally potent inducer of cytoprotective enzymes: elucidation of the structural features that determine inducer potency and reactivity with Keap1.

Authors:  Albena T Dinkova-Kostova; Paul Talalay; John Sharkey; Ying Zhang; W David Holtzclaw; Xiu Jun Wang; Emilie David; Katherine H Schiavoni; Stewart Finlayson; Dale F Mierke; Tadashi Honda
Journal:  J Biol Chem       Date:  2010-08-26       Impact factor: 5.157

2.  A novel acetylenic tricyclic bis-(cyano enone) potently induces phase 2 cytoprotective pathways and blocks liver carcinogenesis induced by aflatoxin.

Authors:  Karen Liby; Mark M Yore; Bill D Roebuck; Karen J Baumgartner; Tadashi Honda; Chitra Sundararajan; Hidenori Yoshizawa; Gordon W Gribble; Charlotte R Williams; Renee Risingsong; Darlene B Royce; Albena T Dinkova-Kostova; Katherine K Stephenson; Patricia A Egner; Melinda S Yates; John D Groopman; Thomas W Kensler; Michael B Sporn
Journal:  Cancer Res       Date:  2008-08-15       Impact factor: 12.701

3.  Pathogenic p62/SQSTM1 mutations impair energy metabolism through limitation of mitochondrial substrates.

Authors:  Fernando Bartolome; Noemi Esteras; Angeles Martin-Requero; Claire Boutoleau-Bretonniere; Martine Vercelletto; Audrey Gabelle; Isabelle Le Ber; Tadashi Honda; Albena T Dinkova-Kostova; John Hardy; Eva Carro; Andrey Y Abramov
Journal:  Sci Rep       Date:  2017-05-10       Impact factor: 4.379

4.  C151 in KEAP1 is the main cysteine sensor for the cyanoenone class of NRF2 activators, irrespective of molecular size or shape.

Authors:  Sharadha Dayalan Naidu; Aki Muramatsu; Ryota Saito; Soichiro Asami; Tadashi Honda; Tomonori Hosoya; Ken Itoh; Masayuki Yamamoto; Takafumi Suzuki; Albena T Dinkova-Kostova
Journal:  Sci Rep       Date:  2018-05-23       Impact factor: 4.379

Review 5.  KEAP1, a cysteine-based sensor and a drug target for the prevention and treatment of chronic disease.

Authors:  Sharadha Dayalan Naidu; Albena T Dinkova-Kostova
Journal:  Open Biol       Date:  2020-06-24       Impact factor: 6.411

6.  (±)-(4bS,8aR,10aS)-10a-Ethynyl-4b,8,8-trimethyl-3,7-dioxo-3,4b,7,8,8a,9,10,10a-octa-hydro-phenanthrene-2,6-dicarbonitrile.

Authors:  Suqing Zheng; Daniel Resch; Tadashi Honda; Jerry P Jasinski
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-10-10

7.  Aldo-keto reductases are biomarkers of NRF2 activity and are co-ordinately overexpressed in non-small cell lung cancer.

Authors:  A Kenneth MacLeod; Lourdes Acosta-Jimenez; Philip J Coates; Michael McMahon; Frank A Carey; Tadashi Honda; Colin J Henderson; C Roland Wolf
Journal:  Br J Cancer       Date:  2016-11-08       Impact factor: 7.640

Review 8.  Essential Role of Keap1-Nrf2 Signaling in Mood Disorders: Overview and Future Perspective.

Authors:  Kenji Hashimoto
Journal:  Front Pharmacol       Date:  2018-10-16       Impact factor: 5.810

9.  High NRF2 Levels Correlate with Poor Prognosis in Colorectal Cancer Patients and with Sensitivity to the Kinase Inhibitor AT9283 In Vitro.

Authors:  Laura Torrente; Gunjit Maan; Asma Oumkaltoum Rezig; Jean Quinn; Angus Jackson; Andrea Grilli; Laura Casares; Ying Zhang; Evgeny Kulesskiy; Jani Saarela; Silvio Bicciato; Joanne Edwards; Albena T Dinkova-Kostova; Laureano de la Vega
Journal:  Biomolecules       Date:  2020-09-25
  9 in total

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