Literature DB >> 20221478

Novel epothilone lactones by an unusual diversion of the Grubbs' metathesis reaction.

Qiao-Hong Chen1, Thota Ganesh, Yi Jiang, Abhijit Banerjee, Shubhada Sharma, Susan Bane, James P Snyder, David G I Kingston.   

Abstract

An unusual reaction with Grubbs' catalyst during the synthesis of bridged epothilones yielded five-membered internal lactones instead of the expected metathesis products. Three of the lactones have activities comparable to epothilone D.

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Year:  2010        PMID： 20221478      PMCID： PMC2930754          DOI： 10.1039/b926174e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  21 in total

1.  The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.

Authors:  T M Trnka; R H Grubbs
Journal:  Acc Chem Res       Date:  2001-01       Impact factor: 22.384

2.  Structural basis of the activity of the microtubule-stabilizing agent epothilone a studied by NMR spectroscopy in solution.

Authors:  Marcel Reese; Víctor M Sánchez-Pedregal; Karel Kubicek; Jens Meiler; Marcel J J Blommers; Christian Griesinger; Teresa Carlomagno
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Conformational preferences of natural and C3-modified epothilones in aqueous solution.

Authors:  Máté Erdélyi; Bernhard Pfeiffer; Kurt Hauenstein; Jörg Fohrer; Jürg Gertsch; Karl-Heinz Altmann; Teresa Carlomagno
Journal:  J Med Chem       Date:  2008-02-14       Impact factor: 7.446

4.  A common pharmacophore for epothilone and taxanes: molecular basis for drug resistance conferred by tubulin mutations in human cancer cells.

Authors:  P Giannakakou; R Gussio; E Nogales; K H Downing; D Zaharevitz; B Bollbuck; G Poy; D Sackett; K C Nicolaou; T Fojo
Journal:  Proc Natl Acad Sci U S A       Date:  2000-03-14       Impact factor: 11.205

5.  A common pharmacophore for Taxol and the epothilones based on the biological activity of a taxane molecule lacking a C-13 side chain.

Authors:  L He; P G Jagtap; D G Kingston; H J Shen; G A Orr; S B Horwitz
Journal:  Biochemistry       Date:  2000-04-11       Impact factor: 3.162

6.  SAR and pH stability of cyano-substituted epothilones.

Authors:  Alicia Regueiro-Ren; Kenneth Leavitt; Soong-Hoon Kim; Gerhard Höfle; Michael Kiffe; Jack Z Gougoutas; John D DiMarco; Francis Y F Lee; Craig R Fairchild; Byron H Long; Gregory D Vite
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

7.  Total synthesis and selective activity of a new class of conformationally restrained epothilones.

Authors:  Mamoun M Alhamadsheh; Shuchi Gupta; Richard A Hudson; Lalith Perera; L M Viranga Tillekeratne
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

8.  Conformation-activity relationships in polyketide natural products. Towards the biologically active conformation of epothilone.

Authors:  Richard E Taylor; Yue Chen; Gabriel M Galvin; Praveen K Pabba
Journal:  Org Biomol Chem       Date:  2003-11-20       Impact factor: 3.876

9.  Design, synthesis and biological evaluation of bridged epothilone D analogues.

Authors:  Qiao-Hong Chen; Thota Ganesh; Peggy Brodie; Carla Slebodnick; Yi Jiang; Abhijit Banerjee; Susan Bane; James P Snyder; David G I Kingston
Journal:  Org Biomol Chem       Date:  2008-11-06       Impact factor: 3.876

10.  Derivation of dihedral angles from CH-CH dipolar-dipolar cross-correlated relaxation rates: a C-C torsion involving a quaternary carbon atom in epothilone A bound to tubulin.

Authors:  Teresa Carlomagno; Víctor M Sánchez; Marcel J J Blommers; Christian Griesinger
Journal:  Angew Chem Int Ed Engl       Date:  2003-06-06       Impact factor: 15.336
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  1 in total

1.  Synthesis of isotopically labeled epothilones.

Authors:  Thota Ganesh; Peggy J Brodie; Abhijit Banerjee; Susan Bane; David G I Kingston
Journal:  J Labelled Comp Radiopharm       Date:  2013-12-05       Impact factor: 1.921
  1 in total

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