Literature DB >> 15913998

Total synthesis and bioactivity of unique flavone desmosdumotin B and its analogs.

Kyoko Nakagawa-Goto1, Kenneth F Bastow, Jiu-Hong Wu, Harukuni Tokuda, Kuo-Hsiung Lee.   

Abstract

The first total synthesis of a unique flavone natural product, desmosdumotin B (1), was accomplished. Furthermore, three novel flavonoids, 6-8, and a novel chalcone, 9, were synthesized. The new compounds were evaluated as in vitro inhibitors of human cancer cell growth. The synthetic 1 showed significant cytotoxic activity against a multi-drug resistant cell line (KB-VIN) with an ED50 value of 2.0 microg/mL compared to >40 microg/mL against the parental KB cell line. Flavone 7 displayed selective activity against 1A9 ovarian carcinoma with an ED50 value of 0.7 microg/mL. Selected 1-analogs and synthetic intermediates were also screened for antitumor-promoting effects as inhibitors of EBV-EA activation. Among them, trihydroxyacetophenone derivatives 11 and 14 showed good activity.

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Year:  2005        PMID: 15913998     DOI: 10.1016/j.bmcl.2005.04.070

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


  9 in total

1.  Antitumor agents. 280. Multidrug resistance-selective desmosdumotin B analogues.

Authors:  Kyoko Nakagawa-Goto; Po-Cheng Chang; Chin-Yu Lai; Hsin-Yi Hung; Tzu-Hsuan Chen; Pei-Chi Wu; Hao Zhu; Alexander Sedykh; Kenneth F Bastow; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2010-09-23       Impact factor: 7.446

2.  Antitumor agents. 284. New desmosdumotin B analogues with bicyclic B-ring as cytotoxic and antitubulin agents.

Authors:  Kyoko Nakagawa-Goto; Pei-Chi Wu; Chin-Yu Lai; Ernest Hamel; Hao Zhu; Liying Zhang; Takashi Kozaka; Emika Ohkoshi; Masuo Goto; Kenneth F Bastow; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2011-02-01       Impact factor: 7.446

3.  Antitumor Agents 291 Expanded B-Ring Modification Study of 6,8,8-Triethyl Desmosdumotin B Analogues as Multidrug-Resistance Selective Agents.

Authors:  Kyoko Nakagawa-Goto; Kenneth F Bastow; Emika Ohkoshi; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  Med Chem (Los Angeles)       Date:  2011-12-01

4.  Design, synthesis and experimental validation of novel potential chemopreventive agents using random forest and support vector machine binary classifiers.

Authors:  Brienne Sprague; Qian Shi; Marlene T Kim; Liying Zhang; Alexander Sedykh; Eiichiro Ichiishi; Harukuni Tokuda; Kuo-Hsiung Lee; Hao Zhu
Journal:  J Comput Aided Mol Des       Date:  2014-05-20       Impact factor: 3.686

5.  Triethylated chromones with substituted naphthalenes as tubulin inhibitors.

Authors:  Kyoko Nakagawa-Goto; Yukako Taniguchi; Yurie Watanabe; Akifumi Oda; Emika Ohkoshi; Ernest Hamel; Kuo-Hsiung Lee; Masuo Goto
Journal:  Bioorg Med Chem       Date:  2016-09-25       Impact factor: 3.641

6.  Development of a novel class of tubulin inhibitor from desmosdumotin B with a hydroxylated bicyclic B-ring.

Authors:  Kyoko Nakagawa-Goto; Akifumi Oda; Ernest Hamel; Emika Ohkoshi; Kuo-Hsiung Lee; Masuo Goto
Journal:  J Med Chem       Date:  2015-02-26       Impact factor: 7.446

7.  Total Synthesis and in Vitro Anti-Tumor-Promoting Activities of Racemic Acetophenone Monomers from Acronychia trifoliolata.

Authors:  Chihiro Morita; Yukiko Kobayashi; Yohei Saito; Katsunori Miyake; Harukuni Tokuda; Nobutaka Suzuki; Eiichiro Ichiishi; Kuo-Hsiung Lee; Kyoko Nakagawa-Goto
Journal:  J Nat Prod       Date:  2016-11-07       Impact factor: 4.050

Review 8.  Is resistance useless? Multidrug resistance and collateral sensitivity.

Authors:  Matthew D Hall; Misty D Handley; Michael M Gottesman
Journal:  Trends Pharmacol Sci       Date:  2009-09-15       Impact factor: 14.819

Review 9.  Targeting the Achilles heel of multidrug-resistant cancer by exploiting the fitness cost of resistance.

Authors:  Gergely Szakács; Matthew D Hall; Michael M Gottesman; Ahcène Boumendjel; Remy Kachadourian; Brian J Day; Hélène Baubichon-Cortay; Attilio Di Pietro
Journal:  Chem Rev       Date:  2014-04-23       Impact factor: 60.622

  9 in total

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