Literature DB >> 17236766

Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: differences of bioactivity in the enantiomeric series.

Nolan R Mente1, Andrew J Wiemer, Jeffrey D Neighbors, John A Beutler, Raymond J Hohl, David F Wiemer.   

Abstract

Total synthesis of the (R,R,R)- and (S,S,S)-enantiomers of the natural product schweinfurthin F has been completed. Comparisons of spectral data and optical rotations with those reported for the natural product, as well as a variety of bioassay data, allow assignment of the natural material as the (R,R,R)-isomer.

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Year:  2006        PMID: 17236766     DOI: 10.1016/j.bmcl.2006.11.096

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


  24 in total

1.  Pleiotropic effects of a schweinfurthin on isoprenoid homeostasis.

Authors:  Sarah A Holstein; Craig H Kuder; Huaxiang Tong; Raymond J Hohl
Journal:  Lipids       Date:  2011-06-02       Impact factor: 1.880

2.  Structural analogues of schweinfurthin F: probing the steric, electronic, and hydrophobic properties of the D-ring substructure.

Authors:  Natalie C Ulrich; John G Kodet; Nolan R Mente; Craig H Kuder; John A Beutler; Raymond J Hohl; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2010-01-04       Impact factor: 3.641

3.  Fluorescent schweinfurthin B and F analogs with anti-proliferative activity.

Authors:  Joseph J Topczewski; Craig H Kuder; Jeffrey D Neighbors; Raymond J Hohl; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2010-07-29       Impact factor: 3.641

4.  Synthesis of indole analogues of the natural schweinfurthins.

Authors:  John G Kodet; David F Wiemer
Journal:  J Org Chem       Date:  2013-09-05       Impact factor: 4.354

5.  Synthesis and structure activity relationships of schweinfurthin indoles.

Authors:  John G Kodet; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2014-03-06       Impact factor: 3.641

6.  Schweinfurthin natural products induce regression of murine melanoma and pair with anti-PD-1 therapy to facilitate durable tumor immunity.

Authors:  Kathleen M Kokolus; Jeremy S Haley; Emily J Koubek; Raghavendra Gowda; Saketh S Dinavahi; Arati Sharma; David F Claxton; Klaus F Helm; Joseph J Drabick; Gavin P Robertson; Jeffrey D Neighbors; Raymond J Hohl; Todd D Schell
Journal:  Oncoimmunology       Date:  2018-11-11       Impact factor: 8.110

7.  Schweinfurthin A selectively inhibits proliferation and Rho signaling in glioma and neurofibromatosis type 1 tumor cells in a NF1-GRD-dependent manner.

Authors:  Thomas J Turbyville; Demirkan B Gürsel; Robert G Tuskan; Jessica C Walrath; Claudia A Lipschultz; Stephen J Lockett; David F Wiemer; John A Beutler; Karlyne M Reilly
Journal:  Mol Cancer Ther       Date:  2010-05-04       Impact factor: 6.261

8.  Relevance of the C-5 position to schweinfurthin induced cytotoxicity.

Authors:  Joseph J Topczewski; Michael P Callahan; John G Kodet; Jery D Inbarasu; Nolan R Mente; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2011-10-19       Impact factor: 3.641

9.  First total synthesis of (+)-Vedelianin, a potent antiproliferative agent.

Authors:  Joseph J Topczewski; David F Wiemer
Journal:  Tetrahedron Lett       Date:  2011-04-06       Impact factor: 2.415

10.  BF3 x Et2O-mediated cascade cyclizations: synthesis of schweinfurthins F and G.

Authors:  Nolan R Mente; Jeffrey D Neighbors; David F Wiemer
Journal:  J Org Chem       Date:  2008-09-17       Impact factor: 4.354

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