2. Academic Validation
  3. Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide

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.
Sergey Vshyvenko 1,  Mary Rose Reisenauer 2,  Snezna Rogelj 2,  Tomas Hudlicky 3
Affiliations

Affiliations

  • 1 Department of Chemistry and Centre for Biotechnology, Brock University, St. Catharines, ON L2S 3A1, Canada.
  • 2 Biology Department, New Mexico Institute of Mining and Technology, Socorro, NM 87801, United States.
  • 3 Department of Chemistry and Centre for Biotechnology, Brock University, St. Catharines, ON L2S 3A1, Canada. Electronic address: thudlicky@brocku.ca.
PMID: 25108300 DOI: 10.1016/j.bmcl.2014.07.034
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.

Keywords

Amaryllidaceae; Anticancer; Biotransformation; Narciclasine; Narciclasine analogs.

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