Literature DB >> 26544765

Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of "Shapeshifting" Properties.

Tian Qin1, Takayuki Iwata1, Tanya T Ransom2, John A Beutler2, John A Porco1.   

Abstract

The 2,4'- and 4,4'-linked variants of the cytotoxic agent secalonic acid A and their analogues have been synthesized. Kinetic resolution of an unprotected tetrahydroxanthone scaffold followed by copper-mediated biaryl coupling allowed for efficient access to these compounds. Evaluation of the "shapeshifting" properties of 2,2'-, 2,4'-, and 4,4'-linked variants of the secalonic acids A in a polar solvent in conjunction with assays of the compounds against select cancer cell lines was conducted to study possible correlations between linkage variation and cytotoxicity.

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Year:  2015        PMID: 26544765      PMCID: PMC4863954          DOI: 10.1021/jacs.5b09825

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  45 in total

1.  Dicerandrols, new antibiotic and cytotoxic dimers produced by the fungus Phomopsis longicolla isolated from an endangered mint.

Authors:  M M Wagenaar; J Clardy
Journal:  J Nat Prod       Date:  2001-08       Impact factor: 4.050

Review 2.  Xanthones from fungi, lichens, and bacteria: the natural products and their synthesis.

Authors:  Kye-Simeon Masters; Stefan Bräse
Journal:  Chem Rev       Date:  2012-05-22       Impact factor: 60.622

3.  Gold-catalyzed halogenation of aromatics by N-halosuccinimides.

Authors:  Fanyang Mo; Jerry Mingtao Yan; Di Qiu; Fei Li; Yan Zhang; Jianbo Wang
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-08       Impact factor: 15.336

4.  Antifouling and antibacterial polyketides from marine gorgonian coral-associated fungus Penicillium sp. SCSGAF 0023.

Authors:  Jie Bao; Yu-Lin Sun; Xiao-Yong Zhang; Zhuang Han; Hai-Chun Gao; Fei He; Pei-Yuan Qian; Shu-Hua Qi
Journal:  J Antibiot (Tokyo)       Date:  2012-12-12       Impact factor: 2.649

5.  A domino approach to the enantioselective total syntheses of blennolide C and gonytolide C.

Authors:  Lutz F Tietze; Stefan Jackenkroll; Judith Hierold; Ling Ma; Bernd Waldecker
Journal:  Chemistry       Date:  2014-06-06       Impact factor: 5.236

6.  Pro-apoptotic and immunostimulatory tetrahydroxanthone dimers from the endophytic fungus Phomopsis longicolla.

Authors:  David Rönsberg; Abdessamad Debbab; Attila Mándi; Vera Vasylyeva; Philip Böhler; Björn Stork; Laura Engelke; Alexandra Hamacher; Richard Sawadogo; Marc Diederich; Victor Wray; WenHan Lin; Matthias U Kassack; Christoph Janiak; Stefanie Scheu; Sebastian Wesselborg; Tibor Kurtán; Amal H Aly; Peter Proksch
Journal:  J Org Chem       Date:  2013-12-11       Impact factor: 4.354

7.  Homobenzotetramisole: an effective catalyst for kinetic resolution of aryl-cycloalkanols.

Authors:  Vladimir B Birman; Ximin Li
Journal:  Org Lett       Date:  2008-02-16       Impact factor: 6.005

8.  Isolation and structure elucidation of parnafungins, antifungal natural products that inhibit mRNA polyadenylation.

Authors:  Craig A Parish; Scott K Smith; Kathleen Calati; Deborah Zink; Kenneth Wilson; Terry Roemer; Bo Jiang; Deming Xu; Gerald Bills; Gonzalo Platas; Fernando Peláez; Maria Teresa Díez; Nancy Tsou; Arlene E McKeown; Richard G Ball; Mary Ann Powles; Lai Yeung; Paul Liberator; Guy Harris
Journal:  J Am Chem Soc       Date:  2008-05-08       Impact factor: 15.419

Review 9.  Xanthone dimers: a compound family which is both common and privileged.

Authors:  Tim Wezeman; Stefan Bräse; Kye-Simeon Masters
Journal:  Nat Prod Rep       Date:  2015-01       Impact factor: 13.423

10.  Stereoselective synthesis of 4-dehydroxydiversonol employing enantioselective palladium-catalysed domino reactions.

Authors:  Lutz F Tietze; Dirk A Spiegl; Florian Stecker; Julia Major; Christian Raith; Christian Große
Journal:  Chemistry       Date:  2008       Impact factor: 5.020

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  11 in total

1.  Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Authors:  Xiaowei Wu; Takayuki Iwata; Adam Scharf; Tian Qin; Kyle D Reichl; John A Porco
Journal:  J Am Chem Soc       Date:  2018-04-25       Impact factor: 15.419

2.  A 2,4'-linked tetrahydroxanthone dimer with protein tyrosine phosphatase 1B inhibitory activity from the Okinawan freshwater Aspergillus sp.

Authors:  Henki Rotinsulu; Hiroyuki Yamazaki; Tomohito Miura; Satomi Chiba; Defny S Wewengkang; Deiske A Sumilat; Michio Namikoshi
Journal:  J Antibiot (Tokyo)       Date:  2017-06-28       Impact factor: 2.649

3.  Synthesis and Anticancer Activity of Structure Simplified Naturally-Inspired Dimeric Chromenone Derivatives.

Authors:  Rameez Ali; Yong Guan; Alexandria N Leveille; Elizabeth Vaughn; Sangram Parelkar; Paul R Thompson; Anita E Mattson
Journal:  European J Org Chem       Date:  2019-08-27

4.  Copper Bis(oxazoline)-Catalyzed Enantioselective Alkynylation of Benzopyrylium Ions.

Authors:  Yong Guan; Jonathan W Attard; Anita E Mattson
Journal:  Chemistry       Date:  2020-01-28       Impact factor: 5.236

5.  Organocatalyzed, Photoredox Heteroarylation of 2-Trifluoroboratochromanones via C-H Functionalization.

Authors:  Jennifer K Matsui; Gary A Molander
Journal:  Org Lett       Date:  2017-02-03       Impact factor: 6.005

Review 6.  Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development.

Authors:  Jennifer K Matsui; Simon B Lang; Drew R Heitz; Gary A Molander
Journal:  ACS Catal       Date:  2017-03-14       Impact factor: 13.084

7.  Carbamoyl-Phosphate Synthase 1 as a Novel Target of Phomoxanthone A, a Bioactive Fungal Metabolite.

Authors:  Sara Ceccacci; Jana Deitersen; Matteo Mozzicafreddo; Elva Morretta; Peter Proksch; Sebastian Wesselborg; Björn Stork; Maria Chiara Monti
Journal:  Biomolecules       Date:  2020-06-02

8.  Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones.

Authors:  Yi Li; Shuang Xin; Rui Weng; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2022-07-05       Impact factor: 9.969

9.  The mycotoxin phomoxanthone A disturbs the form and function of the inner mitochondrial membrane.

Authors:  Philip Böhler; Fabian Stuhldreier; Ruchika Anand; Arun Kumar Kondadi; David Schlütermann; Niklas Berleth; Jana Deitersen; Nora Wallot-Hieke; Wenxian Wu; Marian Frank; Hendrik Niemann; Elisabeth Wesbuer; Andreas Barbian; Tomas Luyten; Jan B Parys; Stefanie Weidtkamp-Peters; Andrea Borchardt; Andreas S Reichert; Aida Peña-Blanco; Ana J García-Sáez; Samuel Itskanov; Alexander M van der Bliek; Peter Proksch; Sebastian Wesselborg; Björn Stork
Journal:  Cell Death Dis       Date:  2018-02-19       Impact factor: 8.469

10.  Amycolachromones A-F, Isolated from a Streptomycin-Resistant Strain of the Deep-Sea Marine Actinomycete Amycolatopsis sp. WP1.

Authors:  Jianwei Chen; Jun Chen; Siqi Wang; Xiaoze Bao; Songwei Li; Bin Wei; Huawei Zhang; Hong Wang
Journal:  Mar Drugs       Date:  2022-02-24       Impact factor: 5.118

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