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Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide
Affiliation: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;1. Laboratorio de Biocatálisis y Biotransformaciones, Departamento de Química Orgánica – Departamento de Biociencias, Facultad de Química, Universidad de la República, Montevideo, Uruguay;2. Química Inorgánica, Departamento Estrella Campos, Facultad de Química, Universidad de la República, Montevideo, Uruguay;1. Marine College, Shandong University at Weihai, No. 180, Wenhua West Road, Weihai 264209, PR China;2. Department of Parasitology, Medical College of Soochow University, Jiangsu 215123, PR China;1. Ioffe Institute, Polytekhnicheskaya 26, St. Petersburg 194021, Russia;2. Peter the Great St. Petersburg Polytechnic University, Polytekhnicheskaya 29, St. Petersburg 195251, Russia
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  Narciclasine  Biotransformation  Anticancer  Narciclasine analogs
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