Display options
Cite
Wender PA, Billingsley KL. Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues. Synthesis (Stuttg). 2013;45(13):1815-1824doi: 10.1055/s-0033-1338860.
Wender, P. A., & Billingsley, K. L. (2013). Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues. Synthesis, 45(13), 1815-1824. https://doi.org/10.1055/s-0033-1338860
Wender, Paul A, and Billingsley, Kelvin L. "Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues." Synthesis vol. 45,13 (2013): 1815-1824. doi: https://doi.org/10.1055/s-0033-1338860
Wender PA, Billingsley KL. Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues. Synthesis (Stuttg). 2013;45(13):1815-1824. doi: 10.1055/s-0033-1338860. PMID: 24672140; PMCID: PMC3963460.
Copy Download .nbib Format: NLM
Share it on

Synthesis (Stuttg). 2013;45(13):1815-1824. doi: 10.1055/s-0033-1338860.

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

Synthesis

Paul A Wender, Kelvin L Billingsley

Affiliations

  1. Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, CA 94305-5080, USA, Fax +1(650)7250259.
  2. Department of Radiology, Stanford University School of Medicine, Stanford, CA 94305-5105, USA.

PMID: 24672140 PMCID: PMC3963460 DOI: 10.1055/s-0033-1338860

Abstract

The design, synthesis, and biological evaluation of a novel class of C13-diversified bryostatin analogues are described. An innovative and general strategy based on a Prins macrocyclization-nucleophilic trapping cascade was used to achieve late-stage diversification. In vitro analysis of selected library members revealed that modification at the C13 position of the bryostatin scaffold can be used as a diversification handle to regulate biological activity.

Keywords: cyclizations; drugs; macrocycles; polyketides

References

  1. J Org Chem. 2013 Jan 4;78(1):104-15 - PubMed
  2. Angew Chem Int Ed Engl. 2010 Nov 2;49(45):8316-26 - PubMed
  3. Proc Natl Acad Sci U S A. 2005 Nov 8;102(45):16432-7 - PubMed
  4. Biochem Pharmacol. 1998 Oct 1;56(7):861-9 - PubMed
  5. Angew Chem Int Ed Engl. 2008;47(17):3242-4 - PubMed
  6. PLoS One. 2010 Jun 16;5(6):e11160 - PubMed
  7. J Med Chem. 2004 Dec 16;47(26):6638-44 - PubMed
  8. Org Lett. 2009 Nov 19;11(22):5342-5 - PubMed
  9. Chem Asian J. 2010 Apr 1;5(4):704-54 - PubMed
  10. Chem Commun (Camb). 2008 Sep 7;(33):3876-8 - PubMed
  11. Science. 2002 Dec 6;298(5600):1912-34 - PubMed
  12. J Am Chem Soc. 2008 Jan 23;130(3):804-5 - PubMed
  13. J Am Chem Soc. 2009 Sep 2;131(34):12406-14 - PubMed
  14. J Am Chem Soc. 2011 Jun 22;133(24):9228-31 - PubMed
  15. Eur J Pharmacol. 2005 Apr 4;512(1):43-51 - PubMed
  16. J Am Chem Soc. 2002 Nov 20;124(46):13648-9 - PubMed
  17. Proc Natl Acad Sci U S A. 1988 Oct;85(19):7197-201 - PubMed
  18. Angew Chem Int Ed Engl. 2000 Jul 3;39(13):2290-2294 - PubMed
  19. Proc Natl Acad Sci U S A. 1998 Jun 9;95(12):6624-9 - PubMed
  20. Acc Chem Res. 2008 Jan;41(1):40-9 - PubMed
  21. Proc Natl Acad Sci U S A. 2008 Sep 9;105(36):13620-5 - PubMed
  22. Proc Natl Acad Sci U S A. 2011 Apr 26;108(17):6721-6 - PubMed
  23. J Org Chem. 2009 Mar 20;74(6):2605-8 - PubMed
  24. Proc Natl Acad Sci U S A. 2009 Aug 25;106(34):14676-80 - PubMed
  25. Exp Hematol. 2009 Jan;37(1):122-134 - PubMed
  26. Org Lett. 2011 Aug 5;13(15):4108-11 - PubMed
  27. J Org Chem. 2010 May 7;75(9):2820-35 - PubMed
  28. Org Lett. 2011 Sep 2;13(17):4652-5 - PubMed
  29. Chem Rev. 2001 Aug;101(8):2353-64 - PubMed
  30. Microb Pathog. 2000 Sep;29(3):187-90 - PubMed
  31. J Am Chem Soc. 2010 Apr 7;132(13):4564-5 - PubMed
  32. J Am Chem Soc. 2011 Sep 7;133(35):13876-9 - PubMed
  33. J Am Chem Soc. 2008 May 28;130(21):6658-9 - PubMed
  34. Org Lett. 2003 Feb 6;5(3):277-9 - PubMed
  35. J Am Chem Soc. 2011 Feb 2;133(4):744-7 - PubMed
  36. Nat Prod Rep. 2002 Aug;19(4):413-53 - PubMed
  37. Org Lett. 2009 Jan 15;11(2):357-60 - PubMed
  38. Org Lett. 2006 Apr 27;8(9):1893-6 - PubMed
  39. Nat Rev Mol Cell Biol. 2010 Feb;11(2):103-12 - PubMed
  40. Clin Cancer Res. 1998 May;4(5):1305-14 - PubMed
  41. J Am Chem Soc. 2008 Oct 1;130(39):13177-81 - PubMed
  42. Biol Bull. 2006 Jun;210(3):201-14 - PubMed
  43. Cancer Immunol Immunother. 1994 Oct;39(4):223-30 - PubMed
  44. Nat Chem. 2012 Sep;4(9):705-10 - PubMed
  45. J Am Chem Soc. 2006 Dec 27;128(51):16480-1 - PubMed
  46. Isr J Chem. 2011 Apr 1;51(3-4):453-472 - PubMed
  47. Nature. 2008 Nov 27;456(7221):485-8 - PubMed
  48. J Am Chem Soc. 2011 Jun 29;133(25):9727-9 - PubMed

Publication Types

Grant support