title: Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide.
abstract: Several unnatural derivatives of narciclasine were prepared in which the C-7 carbon was replaced with nitrogen. The 7-aza derivative and its N-oxide were prepared by the coupling of iodopicolinic acid with a conduramine unit derived chemoenzymatically from bromobenzene. Intramolecular Heck reaction was used to construct the isocarbostyryl ring system. The compounds were submitted to biological screening against cancer cell lines. Full experimental and spectra data are provided for all new compounds.
authors.affiliation: Department of Chemistry and Centre for Biotechnology, Brock University, St. Catharines, ON L2S 3A1, Canada.
authors.forename: Sergey
authors.initials: S
authors.lastname: Vshyvenko
authors.affiliation: Biology Department, New Mexico Institute of Mining and Technology, Socorro, NM 87801, United States.
authors.forename: Mary Rose
authors.initials: MR
authors.lastname: Reisenauer
authors.affiliation: Biology Department, New Mexico Institute of Mining and Technology, Socorro, NM 87801, United States.
authors.forename: Snezna
authors.initials: S
authors.lastname: Rogelj
authors.affiliation: Department of Chemistry and Centre for Biotechnology, Brock University, St. Catharines, ON L2S 3A1, Canada. Electronic address: thudlicky@brocku.ca.
authors.forename: Tomas
authors.initials: T
authors.lastname: Hudlicky
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D061986:MCF-7 Cells; D008968:Molecular Conformation; D010617:Phenanthridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D047151:Amaryllidaceae Alkaloids; D000970:Antineoplastic Agents; D006575:Heterocyclic Compounds, 3-Ring; D010617:Phenanthridines; D011725:Pyridines; D015363:Quinolones; C010753:narciclasine
keywords: Amaryllidaceae; Anticancer; Biotransformation; Narciclasine; Narciclasine analogs
references.citation: J Org Chem. 2002 Dec 13;67(25):8726-43
references.pmid: 12467383
references.citation: Bioorg Med Chem Lett. 2005 Dec 1;15(23):5315-8
references.pmid: 16183280
references.citation: J Med Chem. 2009 Feb 26;52(4):1100-14
references.pmid: 19199649
references.citation: J Org Chem. 2006 Jul 21;71(15):5694-707
references.pmid: 16839151
references.citation: Org Lett. 2002 Jan 10;4(1):115-7
references.pmid: 11772104
references.citation: Angew Chem Int Ed Engl. 2004 Oct 11;43(40):5342-6
references.pmid: 15468184
references.citation: Arch Pharm Res. 2011 Jul;34(7):1065-70
references.pmid: 21811912
references.citation: Bioorg Med Chem Lett. 2004 Jun 7;14(11):2911-5
references.pmid: 15125958
references.citation: Chem Rev. 2008 Jun;108(6):1982-2014
references.pmid: 18489166
references.citation: Angew Chem Int Ed Engl. 2003 Oct 13;42(39):4821-4
references.pmid: 14562359
references.citation: Org Lett. 2010 Jun 4;12(11):2544-7
references.pmid: 20441205
references.citation: J Org Chem. 2010 May 7;75(9):3069-84
references.pmid: 20373760
references.citation: Org Lett. 2006 Sep 14;8(19):4183-6
references.pmid: 16956182
references.citation: Can J Chem. 2012;90(11):932-943
references.pmid: 28017970
references.citation: J Biol Chem. 1989 Sep 5;264(25):14940-6
references.pmid: 2670929
references.citation: Org Biomol Chem. 2013 Jan 21;11(3):515-22
references.pmid: 23207545
references.citation: J Nat Prod. 2008 Mar;71(3):357-63
references.pmid: 18225861
references.citation: J Org Chem. 2009 Sep 18;74(18):7122-31
references.pmid: 19743883
references.citation: Chem Biodivers. 2009 May;6(5):685-91
references.pmid: 19479847
references.citation: J Nat Prod. 2006 Jan;69(1):7-13
references.pmid: 16441059
references.citation: Bioorg Med Chem Lett. 2001 Jan 22;11(2):169-72
references.pmid: 11206451
references.citation: Org Lett. 2008 Jul 3;10(13):2701-4
references.pmid: 18537249
references.citation: Org Prep Proced Int. 2008;40(2):107-161
references.pmid: 27867225
references.citation: Bioorg Med Chem Lett. 2011 Aug 15;21(16):4750-2
references.pmid: 21757350