Cyano Group Removal from Cyano-Promoted Aza-Diels-Alder Adducts: Synthesis and Structure-Activity Relationship of Phenanthroindolizidines and Phenanthroquinolizidines

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...

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Veröffentlicht in:	Organic letters 2016-02, Vol.18 (4), p.638-641
Hauptverfasser:	Chang, Chi-Fen, Li, Chien-Fu, Tsai, Chia-Chen, Chuang, Ta-Hsien
Format:	Artikel
Sprache:	eng
Schlagworte:	2-Propanol - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Borohydrides - chemistry Catalysis Drug Screening Assays, Antitumor Humans Indolizines - chemical synthesis Indolizines - chemistry Molecular Structure Phenanthrolines - chemical synthesis Phenanthrolines - chemistry Quinolizines - chemical synthesis Quinolizines - chemistry Structure-Activity Relationship
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container_end_page	641
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container_title	Organic letters
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creator	Chang, Chi-Fen Li, Chien-Fu Tsai, Chia-Chen Chuang, Ta-Hsien
description	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.
doi_str_mv	10.1021/acs.orglett.5b03395
format	Article
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subjects	2-Propanol - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Borohydrides - chemistry Catalysis Drug Screening Assays, Antitumor Humans Indolizines - chemical synthesis Indolizines - chemistry Molecular Structure Phenanthrolines - chemical synthesis Phenanthrolines - chemistry Quinolizines - chemical synthesis Quinolizines - chemistry Structure-Activity Relationship
title	Cyano Group Removal from Cyano-Promoted Aza-Diels-Alder Adducts: Synthesis and Structure-Activity Relationship of Phenanthroindolizidines and Phenanthroquinolizidines
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