Literature DB >> 27713589

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

Mark E Petersen1, Noemi Kedei2, Nancy E Lewin2, Peter M Blumberg2, Gary E Keck1.   

Abstract

We describe a convergent synthesis of a bryostatin analogue in which the natural A- and B-ring pyrans have been replaced by phenyl rings. The new analogue exhibited PMA like behavior in cell assays, but failed to maintain high affinity binding for PKC, despite retaining an unaltered C-ring 'binding domain'.

Entities:  

Keywords:  Bryostatin; Cross coupling; Heck reaction; PKC; SAR; analogues

Year:  2016        PMID： 27713589      PMCID： PMC5047013          DOI： 10.1016/j.tetlet.2016.09.040

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  27 in total

Review 1.  New approaches to the total synthesis of the bryostatin antitumor macrolides.

Authors:  Karl J Hale; Soraya Manaviazar
Journal:  Chem Asian J       Date:  2010-04-01

2.  Total synthesis of bryostatin 1.

Authors:  Gary E Keck; Yam B Poudel; Thomas J Cummins; Arnab Rudra; Jonathan A Covel
Journal:  J Am Chem Soc       Date:  2010-12-22       Impact factor: 15.419

3.  Late-stage intermolecular CH activation for lead diversification: a highly chemoselective oxyfunctionalization of the C-9 position of potent bryostatin analogues.

Authors:  Paul A Wender; Michael K Hilinski; Alexander V W Mayweg
Journal:  Org Lett       Date:  2005-01-06       Impact factor: 6.005

4.  Cocarcinogenic principles from the seed oil of Croton tiglium and from other Euphorbiaceae.

Authors:  E Hecker
Journal:  Cancer Res       Date:  1968-11       Impact factor: 12.701

5.  Molecular modeling, total synthesis, and biological evaluations of C9-deoxy bryostatin 1.

Authors:  Gary E Keck; Yam B Poudel; Arnab Rudra; Jeffrey C Stephens; Noemi Kedei; Nancy E Lewin; Megan L Peach; Peter M Blumberg
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-21       Impact factor: 15.336

Review 6.  Activation of latent HIV-1 expression by protein kinase C agonists. A novel therapeutic approach to eradicate HIV-1 reservoirs.

Authors:  Gonzalo Sánchez-Duffhues; Minh Q Vo; Moisés Pérez; Marco A Calzado; Santiago Moreno; Giovanni Appendino; Eduardo Muñoz
Journal:  Curr Drug Targets       Date:  2011-03-01       Impact factor: 3.465

7.  Modeling of the bryostatins to the phorbol ester pharmacophore on protein kinase C.

Authors:  P A Wender; C M Cribbs; K F Koehler; N A Sharkey; C L Herald; Y Kamano; G R Pettit; P M Blumberg
Journal:  Proc Natl Acad Sci U S A       Date:  1988-10       Impact factor: 11.205

8.  Therapeutic effects of PKC activators in Alzheimer's disease transgenic mice.

Authors:  René Etcheberrigaray; Mathew Tan; Ilse Dewachter; Cuno Kuipéri; Ingrid Van der Auwera; Stefaan Wera; Lixin Qiao; Barry Bank; Thomas J Nelson; Alan P Kozikowski; Fred Van Leuven; Daniel L Alkon
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-19       Impact factor: 11.205

9.  The bryostatin 1 A-ring acetate is not the critical determinant for antagonism of phorbol ester-induced biological responses.

Authors:  Gary E Keck; Wei Li; Matthew B Kraft; Noemi Kedei; Nancy E Lewin; Peter M Blumberg
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

10.  Role of the C8 gem-dimethyl group of bryostatin 1 on its unique pattern of biological activity.

Authors:  Gary E Keck; Yam B Poudel; Arnab Rudra; Jeffrey C Stephens; Noemi Kedei; Nancy E Lewin; Peter M Blumberg
Journal:  Bioorg Med Chem Lett       Date:  2012-04-24       Impact factor: 2.823
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.