Literature DB >> 20529690

Syntheses and biological evaluation of ring-C modified colchicine analogs.

Baiyuan Yang1, Zhiqing C Zhu, Holly V Goodson, Marvin J Miller.   

Abstract

Ring-C modified alkaloids were synthesized from colchicine using iminonitroso Diels-Alder reactions in a highly regio- and stereoselective fashion. Several analogs exhibited cytotoxic activity similar to that of colchicine itself against PC-3 and MCF-7 cancer cell lines, by serving as prodrugs of colchicine through retro Diels-Alder reactions under the assayed conditions. In vitro microtubule polymerization assays indicated that these modifications affected their interaction with tubulin. Copyright 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 20529690      PMCID： PMC2883562          DOI： 10.1016/j.bmcl.2010.03.056

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


  8 in total

1.  Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain.

Authors:  Raimond B G Ravelli; Benoît Gigant; Patrick A Curmi; Isabelle Jourdain; Sylvie Lachkar; André Sobel; Marcel Knossow
Journal:  Nature       Date:  2004-03-11       Impact factor: 49.962

2.  Mechanism of tubulin-colchicine recognition: a kinetic study of the binding of the colchicine analogues colchicide and isocolchicine.

Authors:  C Dumortier; Q Yan; S Bane; Y Engelborghs
Journal:  Biochem J       Date:  1997-11-01       Impact factor: 3.857

Review 3.  Novel antitumor agents from higher plants.

Authors:  K H Lee
Journal:  Med Res Rev       Date:  1999-11       Impact factor: 12.944

4.  The binding of isocolchicine to tubulin. Mechanisms of ligand association with tubulin.

Authors:  S B Hastie; R C Williams; D Puett; T L Macdonald
Journal:  J Biol Chem       Date:  1989-04-25       Impact factor: 5.157

5.  Toxicity quantitative structure--activity relationships of colchicines.

Authors:  F R Quinn; Z Neiman; J A Beisler
Journal:  J Med Chem       Date:  1981-05       Impact factor: 7.446

Review 6.  Anti-mitotic activity of colchicine and the structural basis for its interaction with tubulin.

Authors:  Bhabatarak Bhattacharyya; Dulal Panda; Suvroma Gupta; Mithu Banerjee
Journal:  Med Res Rev       Date:  2008-01       Impact factor: 12.944

7.  Iminonitroso Diels-Alder reactions for efficient derivatization and functionalization of complex diene-containing natural products.

Authors:  Fangzheng Li; Baiyuan Yang; Marvin J Miller; Jaroslav Zajicek; Bruce C Noll; Ute Möllmann; Hans-Martin Dahse; Patricia A Miller
Journal:  Org Lett       Date:  2007-06-30       Impact factor: 6.005

8.  Retro iminonitroso Diels-Alder reactions: interconversion of nitroso cycloadducts.

Authors:  Baiyuan Yang; Weimin Lin; Viktor Krchnak; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2009-10-01       Impact factor: 2.415
  8 in total
  4 in total

Review 1.  Nitroso Diels-Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products.

Authors:  Serena Carosso; Marvin J Miller
Journal:  Org Biomol Chem       Date:  2014-10-14       Impact factor: 3.876

Review 2.  Reviewing Colchicaceae alkaloids - perspectives of evolution on medicinal chemistry.

Authors:  Sonny Larsson; Nina Rønsted
Journal:  Curr Top Med Chem       Date:  2014       Impact factor: 3.295

Review 3.  Stereo- and regioselectivity of the hetero-Diels-Alder reaction of nitroso derivatives with conjugated dienes.

Authors:  Lucie Brulíková; Aidan Harrison; Marvin J Miller; Jan Hlaváč
Journal:  Beilstein J Org Chem       Date:  2016-09-01       Impact factor: 2.883

4.  Colchicine-like β-acetamidoketones as inhibitors of microtubule polymerization: Design, synthesis and biological evaluation of in vitro anticancer activity.

Authors:  Ehsan Karimikia; Javad Behravan; Afshin Zarghi; Morteza Ghandadi; Sina Omid Malayeri; Razieh Ghodsi
Journal:  Iran J Basic Med Sci       Date:  2019-10       Impact factor: 2.699
  4 in total

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