Literature DB >> 22819765

Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity.

Igor V Magedov1, Artem S Kireev, Aaron R Jenkins, Nikolai M Evdokimov, Dustin T Lima, Paul Tongwa, Jeff Altig, Wim F A Steelant, Severine Van slambrouck, Mikhail Yu Antipin, Alexander Kornienko.   

Abstract

4H-Pyrano-[2,3-b]naphthoquinone is a structural motif commonly found in natural products manifesting anticancer activities. As part of a program aimed at structural simplification of bioactive natural products utilizing multicomponent synthetic processes, we developed a compound library based on this heterocyclic scaffold. We found that several library members displayed low micromolar antiproliferative activity and induced apoptosis in human cancer cells. Selected compounds showed promising activity against cancer cell lines resistant to proapoptotic stimuli, demonstrating their potential in treating cancers with dismal prognoses.
Copyright © 2012 Elsevier Ltd. All rights reserved.

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Year:  2012        PMID： 22819765      PMCID： PMC3856941          DOI： 10.1016/j.bmcl.2012.06.073

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


  19 in total

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3.  Anticancer properties of an important drug lead podophyllotoxin can be efficiently mimicked by diverse heterocyclic scaffolds accessible via one-step synthesis.

Authors:  Igor V Magedov; Liliya Frolova; Madhuri Manpadi; Uma devi Bhoga; Hong Tang; Nikolai M Evdokimov; Olivia George; Kathy Hadje Georgiou; Steffen Renner; Matthäus Getlik; Tiffany L Kinnibrugh; Manuel A Fernandes; Severine Van slambrouck; Wim F A Steelant; Charles B Shuster; Snezna Rogelj; Willem A L van Otterlo; Alexander Kornienko
Journal:  J Med Chem       Date:  2011-05-26       Impact factor: 7.446

Review 4.  Drug resistance in melanoma: new perspectives.

Authors:  Caterina A M La Porta
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5.  Structural simplification of bioactive natural products with multicomponent synthesis. 3. Fused uracil-containing heterocycles as novel topoisomerase-targeting agents.

Authors:  Nikolai M Evdokimov; Severine Van Slambrouck; Petra Heffeter; Lee Tu; Benjamin Le Calvé; Delphine Lamoral-Theys; Carla J Hooten; Pavel Y Uglinskii; Snezna Rogelj; Robert Kiss; Wim F A Steelant; Walter Berger; Jeremy J Yang; Cristian G Bologa; Alexander Kornienko; Igor V Magedov
Journal:  J Med Chem       Date:  2011-03-09       Impact factor: 7.446

6.  Design and synthesis of a novel series of pyranonaphthoquinones as topoisomerase II catalytic inhibitors.

Authors:  Sandra Jiménez-Alonso; Haydee Chávez Orellana; Ana Estévez-Braun; Angel G Ravelo; Elisa Pérez-Sacau; Felix Machín
Journal:  J Med Chem       Date:  2008-09-25       Impact factor: 7.446

7.  Novel one-pot three- and pseudo-five-component reactions: synthesis of functionalized benzo[g]- and dihydropyrano[2,3-g]chromene derivatives.

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8.  Three-component synthesis and anticancer evaluation of polycyclic indenopyridines lead to the discovery of a novel indenoheterocycle with potent apoptosis inducing properties.

Authors:  Madhuri Manpadi; Pavel Y Uglinskii; Shiva K Rastogi; Karen M Cotter; Yin-Shan C Wong; Lisa A Anderson; Amber J Ortega; Severine Van Slambrouck; Wim F A Steelant; Snezna Rogelj; Paul Tongwa; Mikhail Yu Antipin; Igor V Magedov; Alexander Kornienko
Journal:  Org Biomol Chem       Date:  2007-10-24       Impact factor: 3.876

9.  Structural simplification of bioactive natural products with multicomponent synthesis. 2. antiproliferative and antitubulin activities of pyrano[3,2-c]pyridones and pyrano[3,2-c]quinolones.

Authors:  Igor V Magedov; Madhuri Manpadi; Marcia A Ogasawara; Adriana S Dhawan; Snezna Rogelj; Severine Van Slambrouck; Wim F A Steelant; Nikolai M Evdokimov; Pavel Y Uglinskii; Eerik M Elias; Erica J Knee; Paul Tongwa; Mikhail Yu Antipin; Alexander Kornienko
Journal:  J Med Chem       Date:  2008-03-25       Impact factor: 7.446

10.  Antiproliferative and apoptosis inducing properties of pyrano[3,2-c]pyridones accessible by a one-step multicomponent synthesis.

Authors:  Igor V Magedov; Madhuri Manpadi; Nikolai M Evdokimov; Eerik M Elias; Elena Rozhkova; Marcia A Ogasawara; Jennifer D Bettale; Nikolai M Przheval'skii; Snezna Rogelj; Alexander Kornienko
Journal:  Bioorg Med Chem Lett       Date:  2007-05-06       Impact factor: 2.823
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  3 in total

1.  Exploring natural product chemistry and biology with multicomponent reactions. 5. Discovery of a novel tubulin-targeting scaffold derived from the rigidin family of marine alkaloids.

Authors:  Liliya V Frolova; Igor V Magedov; Anntherese E Romero; Menuka Karki; Isaiah Otero; Kathryn Hayden; Nikolai M Evdokimov; Laetitia Moreno Y Banuls; Shiva K Rastogi; W Ross Smith; Shi-Long Lu; Robert Kiss; Charles B Shuster; Ernest Hamel; Tania Betancourt; Snezna Rogelj; Alexander Kornienko
Journal:  J Med Chem       Date:  2013-08-23       Impact factor: 7.446

2.  A new 4-(pyridinyl)-4H-benzo[g]chromene-5,10-dione ruthenium(II) complex inducing senescence in 518A2 melanoma cells.

Authors:  Madeleine Gold; Yusufi Mujahid; Khursheed Ahmed; Hana Kostrhunova; Jana Kasparkova; Viktor Brabec; Bernhard Biersack; Rainer Schobert
Journal:  J Biol Inorg Chem       Date:  2019-06-19       Impact factor: 3.358

Review 3.  Structural simplification: an efficient strategy in lead optimization.

Authors:  Shengzheng Wang; Guoqiang Dong; Chunquan Sheng
Journal:  Acta Pharm Sin B       Date:  2019-06-06       Impact factor: 11.413
  3 in total

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