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Literature DB >> 18355076

Design and synthesis of C6-C8 bridged epothilone A.

Weiqiang Zhan¹, Yi Jiang, Peggy J Brodie, David G I Kingston, Dennis C Liotta, James P Snyder.

Abstract

A conformationally restrained epothilone A analogue (3) with a short bridge between methyl groups at C6 and C8 was designed and synthesized. Preliminary biological evaluation indicates 3 to be only weakly active (IC50 = 8.5 microM) against the A2780 human ovarian cancer cell line.

Entities: Chemical Disease Species

Mesh：

Substances：
Epothilones
epothilone A

Year: 2008 PMID： 18355076 PMCID： PMC3249659 DOI： 10.1021/ol800422q

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

21 in total

Review 1. Epothilones and related structures--a new class of microtubule inhibitors with potent in vivo antitumor activity.

Authors: K H Altmann; M Wartmann; T O'Reilly
Journal: Biochim Biophys Acta Date: 2000-05-17

2. Total synthesis and antitumor activity of ZK-EPO: the first fully synthetic epothilone in clinical development.

Authors: Ulrich Klar; Bernd Buchmann; Wolfgang Schwede; Werner Skuballa; Jens Hoffmann; Rosemarie B Lichtner
Journal: Angew Chem Int Ed Engl Date: 2006-12-04 Impact factor: 15.336

3. Paclitaxel-resistant human ovarian cancer cells have mutant beta-tubulins that exhibit impaired paclitaxel-driven polymerization.

Authors: P Giannakakou; D L Sackett; Y K Kang; Z Zhan; J T Buters; T Fojo; M S Poruchynsky
Journal: J Biol Chem Date: 1997-07-04 Impact factor: 5.157

4. Epothilons A and B: antifungal and cytotoxic compounds from Sorangium cellulosum (Myxobacteria). Production, physico-chemical and biological properties.

Authors: K Gerth; N Bedorf; G Höfle; H Irschik; H Reichenbach
Journal: J Antibiot (Tokyo) Date: 1996-06 Impact factor: 2.649

5. The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis A list of abbreviations can be found at the end of the article.

Authors: Sherry R. Chemler; Dirk Trauner; Samuel J. Danishefsky
Journal: Angew Chem Int Ed Engl Date: 2001-12-17 Impact factor: 15.336

6. Cloning and heterologous expression of the epothilone gene cluster.

Authors: L Tang; S Shah; L Chung; J Carney; L Katz; C Khosla; B Julien
Journal: Science Date: 2000-01-28 Impact factor: 47.728

7. Intramolecular Diels-Alder reactions using alpha-methylene lactones as dienophile.

Authors: Frank Richter; Matthias Bauer; Caroline Perez; Cäcilia Maichle-Mössmer; Martin E Maier
Journal: J Org Chem Date: 2002-04-19 Impact factor: 4.354

8. 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

9. Metal-catalyzed cycloisomerization of enyne functionalities via a 1,3-alkylidene migration.

Authors: Ming-Yuan Lin; Arindam Das; Rai-Shung Liu
Journal: J Am Chem Soc Date: 2006-07-26 Impact factor: 15.419

Review 10. Epothilones as lead structures for the synthesis-based discovery of new chemotypes for microtubule stabilization.

Authors: Fabian Feyen; Frédéric Cachoux; Jürg Gertsch; Markus Wartmann; Karl-Heinz Altmann
Journal: Acc Chem Res Date: 2007-12-27 Impact factor: 22.384

5 in total

5. Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, two potent new microtubule-stabilizing agents.

Authors: María Jiménez; Wei Zhu; Andreas Vogt; Billy W Day; Dennis P Curran
Journal: Beilstein J Org Chem Date: 2011-10-05 Impact factor: 2.883