Literature DB >> 20116262

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

Natalie C Ulrich1, John G Kodet, Nolan R Mente, Craig H Kuder, John A Beutler, Raymond J Hohl, David F Wiemer.   

Abstract

The natural tetracyclic schweinfurthins are potent and selective inhibitors of cell growth in the National Cancer Institute's 60-cell line screen. An interest in determination of their cellular or molecular target has inspired our efforts to prepare both the natural products and analogues. In this paper, chemical synthesis of analogues modified in different olefinic positions, and preliminary results from studies of their biological activity, are reported. Copyright 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID: 20116262      PMCID: PMC5520629          DOI: 10.1016/j.bmc.2009.12.063

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  15 in total

1.  Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization.

Authors:  L Pieters; S Van Dyck; M Gao; R Bai; E Hamel; A Vlietinck; G Lemière
Journal:  J Med Chem       Date:  1999-12-30       Impact factor: 7.446

2.  Synthesis and structure-activity studies of schweinfurthin B analogs: Evidence for the importance of a D-ring hydrogen bond donor in expression of differential cytotoxicity.

Authors:  Jeffrey D Neighbors; Maya S Salnikova; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2005-11-14       Impact factor: 3.641

3.  Synthesis of nonracemic 3-deoxyschweinfurthin B.

Authors:  Jeffrey D Neighbors; John A Beutler; David F Wiemer
Journal:  J Org Chem       Date:  2005-02-04       Impact factor: 4.354

4.  Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.

Authors:  J A Beutler; R H Shoemaker; T Johnson; M R Boyd
Journal:  J Nat Prod       Date:  1998-12       Impact factor: 4.050

5.  An information-intensive approach to the molecular pharmacology of cancer.

Authors:  J N Weinstein; T G Myers; P M O'Connor; S H Friend; A J Fornace; K W Kohn; T Fojo; S E Bates; L V Rubinstein; N L Anderson; J K Buolamwini; W W van Osdol; A P Monks; D A Scudiero; E A Sausville; D W Zaharevitz; B Bunow; V N Viswanadhan; G S Johnson; R E Wittes; K D Paull
Journal:  Science       Date:  1997-01-17       Impact factor: 47.728

6.  Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest.

Authors:  Brent J Yoder; Shugeng Cao; Andrew Norris; James S Miller; Fidy Ratovoson; Jeremi Razafitsalama; Rabodo Andriantsiferana; Vincent E Rasamison; David G I Kingston
Journal:  J Nat Prod       Date:  2007-02-28       Impact factor: 4.050

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

Authors:  Nolan R Mente; Andrew J Wiemer; Jeffrey D Neighbors; John A Beutler; Raymond J Hohl; David F Wiemer
Journal:  Bioorg Med Chem Lett       Date:  2006-12-12       Impact factor: 2.823

8.  Total synthesis of (+)-schweinfurthins B and E.

Authors:  Joseph J Topczewski; Jeffrey D Neighbors; David F Wiemer
Journal:  J Org Chem       Date:  2009-09-18       Impact factor: 4.354

9.  Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents.

Authors:  Marinella Roberti; Daniela Pizzirani; Daniele Simoni; Riccardo Rondanin; Riccardo Baruchello; Caterina Bonora; Filippo Buscemi; Stefania Grimaudo; Manlio Tolomeo
Journal:  J Med Chem       Date:  2003-07-31       Impact factor: 7.446

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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  16 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.  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

3.  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

4.  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

5.  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

6.  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

7.  Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.

Authors:  Joseph J Topczewski; John G Kodet; David F Wiemer
Journal:  J Org Chem       Date:  2011-01-12       Impact factor: 4.354

Review 8.  Modern natural products drug discovery and its relevance to biodiversity conservation.

Authors:  David G I Kingston
Journal:  J Nat Prod       Date:  2010-12-07       Impact factor: 4.050

9.  Functional evaluation of a fluorescent schweinfurthin: mechanism of cytotoxicity and intracellular quantification.

Authors:  Craig H Kuder; Ryan M Sheehy; Jeffrey D Neighbors; David F Wiemer; Raymond J Hohl
Journal:  Mol Pharmacol       Date:  2012-03-29       Impact factor: 4.436

10.  Synthesis of amide isosteres of schweinfurthin-based stilbenes.

Authors:  David P Stockdale; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2017-08-09       Impact factor: 3.641

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