Comparative Study
doi: 10.1016/j.bmcl.2005.08.024.
Epub 2005 Sep 23.
A synthesis of 3-deoxydihydrolycoricidine: refinement of a structurally minimum pancratistatin pharmacophore
Affiliations
- PMID: 16183280
- DOI: 10.1016/j.bmcl.2005.08.024
Item in Clipboard
Comparative Study
A synthesis of 3-deoxydihydrolycoricidine: refinement of a structurally minimum pancratistatin pharmacophore
Bioorg Med Chem Lett.
.
Abstract
The synthesis of 3-deoxydihydrolycoricidine, a key element toward elucidation of the pancratistatin anticancer pharmacophore, is described. Biological evaluation of this compound showed it to be significantly less active against tumor cells than pancratistatin. In addition to those features previously identified, the requirement of a 2,3,4-triol functionalized ring-C is now definitely established as the minimum pharmacophoric element for potent anticancer activity.
Similar articles
-
synthesis and biological evaluation of fully functionalized seco-pancratistatin analogues.J Nat Prod. 2008 Mar;71(3):357-63. doi: 10.1021/np0705460. Epub 2008 Jan 29. J Nat Prod. 2008. PMID: 18225861
-
Synthesis and biological evaluation of aromatic analogues of conduritol F, L-chiro-inositol, and dihydroconduritol F structurally related to the amaryllidaceae anticancer constituents.J Org Chem. 2006 Jul 21;71(15):5694-707. doi: 10.1021/jo0607562. J Org Chem. 2006. PMID: 16839151
-
Structure-activity studies on seco-pancratistatin analogs: potent inhibitors of human cytochrome P450 3A4.Bioorg Med Chem Lett. 2009 Oct 1;19(19):5607-12. doi: 10.1016/j.bmcl.2009.08.032. Epub 2009 Aug 13. Bioorg Med Chem Lett. 2009. PMID: 19713107
-
Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives.Angew Chem Int Ed Engl. 2016 May 4;55(19):5642-91. doi: 10.1002/anie.201508227. Epub 2016 Mar 11. Angew Chem Int Ed Engl. 2016. PMID: 26969844 Review.
-
Applications of total synthesis toward the discovery of clinically useful anticancer agents.Chem Soc Rev. 2007 Aug;36(8):1207-26. doi: 10.1039/b611967k. Epub 2007 Jun 6. Chem Soc Rev. 2007. PMID: 17619682 Review.
Cited by
-
Conversion of Natural Narciclasine to Its C-1 and C-6 Derivatives and Their Antitumor Activity Evaluation: Some Unusual Chemistry of Narciclasine.Molecules. 2022 Jun 28;27(13):4141. doi: 10.3390/molecules27134141. Molecules. 2022. PMID: 35807391 Free PMC article.
-
Amaryllidaceae isocarbostyril alkaloids and their derivatives as promising antitumor agents.Transl Oncol. 2008 Mar;1(1):1-13. doi: 10.1593/tlo.08100. Transl Oncol. 2008. PMID: 18607503 Free PMC article.
-
A novel synthetic C-1 analogue of 7-deoxypancratistatin induces apoptosis in p53 positive and negative human colorectal cancer cells by targeting the mitochondria: enhancement of activity by tamoxifen.Invest New Drugs. 2012 Jun;30(3):1012-27. doi: 10.1007/s10637-011-9668-7. Epub 2011 Apr 15. Invest New Drugs. 2012. PMID: 21494837
-
TOTAL SYNTHESES OF PANCRATISTATIN. A REVIEW.Org Prep Proced Int. 2008;40(2):107-161. doi: 10.1080/00304940809458083. Epub 2009 Feb 18. Org Prep Proced Int. 2008. PMID: 27867225 Free PMC article. No abstract available.
-
Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide.Bioorg Med Chem Lett. 2014 Sep 1;24(17):4236-8. doi: 10.1016/j.bmcl.2014.07.034. Epub 2014 Jul 19. Bioorg Med Chem Lett. 2014. PMID: 25108300 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
