title: Cyano Group Removal from Cyano-Promoted Aza-Diels-Alder Adducts: Synthesis and Structure-Activity Relationship of Phenanthroindolizidines and Phenanthroquinolizidines.
abstract: Phenanthroindolizidines and phenanthroquinolizidines were concisely synthesized by the reductive decyanization of cyano-promoted intramolecular aza-Diels-Alder cycloadducts followed by aryl-aryl coupling. Cyano groups were removed from α-aminoacrylonitriles via treatment with sodium borohydride in 2-propanol in almost quantitative yields; a possible mechanism was proposed and examined using D-labeling experiments. A systematic study of the effects of the phenanthrene substitution pattern on the anticancer activity against three human cancer cell lines was discussed.
authors.affiliation: Department of Anatomy, School of Medicine, China Medical University , Taichung 40402, Taiwan.
authors.forename: Chi-Fen
authors.initials: CF
authors.lastname: Chang
authors.affiliation: School of Pharmacy, China Medical University , Taichung 40402, Taiwan.
authors.forename: Chien-Fu
authors.initials: CF
authors.lastname: Li
authors.affiliation: School of Pharmacy, China Medical University , Taichung 40402, Taiwan.
authors.forename: Chia-Chen
authors.initials: CC
authors.lastname: Tsai
authors.affiliation: School of Pharmacy, China Medical University , Taichung 40402, Taiwan.|Research Center for Chinese Herbal Medicine, China Medical University , Taichung 40402, Taiwan.
authors.forename: Ta-Hsien
authors.initials: TH
authors.lastname: Chuang
mesh_terms: D019840:2-Propanol / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001894:Borohydrides / Q000737:chemistry; D002384:Catalysis; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001894:Borohydrides; D007212:Indolizines; D010618:Phenanthrolines; D011807:Quinolizines; C521640:phenanthroindolizidine; C521641:phenanthroquinolizidine; C025364:sodium borohydride; D019840:2-Propanol