Literature DB >> 22661768

Translating Nature's Library: The Bryostatins and Function-Oriented Synthesis.

Paul A Wender1, Brian A Loy, Adam J Schrier.   

Abstract

We review in part our computational, design, synthesis, and biological studies on a remarkable class of compounds and their designed analogs that have led to preclinical candidates for the treatment of cancer, a first-in-class approach to Alzheimer's disease, and a promising strategy to eradicate HIV/AIDS. Because these leads target, in part, protein kinase C (PKC) isozymes, they have therapeutic potential even beyond this striking set of therapeutic indications. This program has given rise to new synthetic methodology and represents an increasingly important direction of synthesis focused on achieving function through synthesis-informed design (function-oriented synthesis).

Entities:  

Year:  2011        PMID: 22661768      PMCID: PMC3364006          DOI: 10.1002/ijch.201100020

Source DB:  PubMed          Journal:  Isr J Chem        ISSN: 0021-2148            Impact factor:   3.333


  92 in total

1.  Design, synthesis, and biological evaluation of a potent, PKC selective, B-ring analog of bryostatin.

Authors:  Paul A Wender; Vishal A Verma
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

Review 2.  Targeting the protein kinase C family: are we there yet?

Authors:  Helen J Mackay; Christopher J Twelves
Journal:  Nat Rev Cancer       Date:  2007-07       Impact factor: 60.716

3.  The design, synthesis, and evaluation of C7 diversified bryostatin analogs reveals a hot spot for PKC affinity.

Authors:  Paul A Wender; Vishal A Verma
Journal:  Org Lett       Date:  2008-06-28       Impact factor: 6.005

4.  Asymmetric synthesis of the northern half C1-C16 of the bryostatins.

Authors:  A Vakalopoulos; T F Lampe; H M Hoffmann
Journal:  Org Lett       Date:  2001-03-22       Impact factor: 6.005

5.  Function-oriented synthesis of simplified caprazamycins: discovery of oxazolidine-containing uridine derivatives as antibacterial agents against drug-resistant bacteria.

Authors:  Kensuke Ii; Satoshi Ichikawa; Bayan Al-Dabbagh; Ahmed Bouhss; Akira Matsuda
Journal:  J Med Chem       Date:  2010-05-13       Impact factor: 7.446

Review 6.  Function-oriented synthesis, step economy, and drug design.

Authors:  Paul A Wender; Vishal A Verma; Thomas J Paxton; Thomas H Pillow
Journal:  Acc Chem Res       Date:  2007-12-27       Impact factor: 22.384

7.  Total synthesis and structural revision of the marine macrolide neopeltolide.

Authors:  Daniel W Custar; Thomas P Zabawa; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2008-01-23       Impact factor: 15.419

8.  Total synthesis of (-)-exiguolide.

Authors:  Haruhiko Fuwa; Makoto Sasaki
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

9.  Potent cytotoxins produced by a microbial symbiont protect host larvae from predation.

Authors:  Nicole Lopanik; Niels Lindquist; Nancy Targett
Journal:  Oecologia       Date:  2004-01-28       Impact factor: 3.225

10.  All-atom model for stabilization of alpha-helical structure in peptides by hydrocarbon staples.

Authors:  Peter S Kutchukian; Jae Shick Yang; Gregory L Verdine; Eugene I Shakhnovich
Journal:  J Am Chem Soc       Date:  2009-04-08       Impact factor: 15.419

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  16 in total

1.  The many hats of protein kinase Cδ: one enzyme with many functions.

Authors:  Nir Qvit; Daria Mochly-Rosen
Journal:  Biochem Soc Trans       Date:  2014-12       Impact factor: 5.407

2.  Enantioselective synthesis of (-)-exiguolide by iterative stereoselective dioxinone-directed Prins cyclizations.

Authors:  Erika A Crane; Thomas P Zabawa; Rebecca L Farmer; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-19       Impact factor: 15.336

3.  Toward the Ideal Synthesis and Transformative Therapies: The Roles of Step Economy and Function Oriented Synthesis.

Authors:  Paul A Wender
Journal:  Tetrahedron       Date:  2013-06-07       Impact factor: 2.457

Review 4.  Conformation-activity relationships of polyketide natural products.

Authors:  Erik M Larsen; Matthew R Wilson; Richard E Taylor
Journal:  Nat Prod Rep       Date:  2015-08       Impact factor: 13.423

5.  Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues.

Authors:  Paul A Wender; Kelvin L Billingsley
Journal:  Synthesis (Stuttg)       Date:  2013       Impact factor: 3.157

6.  Function Oriented Synthesis: Preparation and Initial Biological Evaluation of New A-Ring-Modified Bryologs.

Authors:  Paul A Wender; Jenny Reuber
Journal:  Tetrahedron       Date:  2011-12-23       Impact factor: 2.457

7.  Evaluation of Chromane-Based Bryostatin Analogues Prepared via Hydrogen-Mediated C-C Bond Formation: Potency Does Not Confer Bryostatin-like Biology.

Authors:  John M Ketcham; Ivan Volchkov; Te-Yu Chen; Peter M Blumberg; Noemi Kedei; Nancy E Lewin; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-09-27       Impact factor: 15.419

8.  Mechanistic and computational studies of exocyclic stereocontrol in the synthesis of bryostatin-like cis-2,6-disubstituted 4-alkylidenetetrahydropyrans by Prins cyclization.

Authors:  Yasuyuki Ogawa; Phillip P Painter; Dean J Tantillo; Paul A Wender
Journal:  J Org Chem       Date:  2012-11-07       Impact factor: 4.354

9.  Replacement of the Bryostatin A- and B-Pyran Rings With Phenyl Rings Leads to Loss of High Affinity Binding With PKC.

Authors:  Mark E Petersen; Noemi Kedei; Nancy E Lewin; Peter M Blumberg; Gary E Keck
Journal:  Tetrahedron Lett       Date:  2016-10-19       Impact factor: 2.415

10.  Designed, synthetically accessible bryostatin analogues potently induce activation of latent HIV reservoirs in vitro.

Authors:  Brian A DeChristopher; Brian A Loy; Matthew D Marsden; Adam J Schrier; Jerome A Zack; Paul A Wender
Journal:  Nat Chem       Date:  2012-07-15       Impact factor: 24.427

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