84416-06-8Relevant academic research and scientific papers
PHENANTHROINDOLIZIDINE AND PHENANTHROQUINOLIZIDINE ALKALOID HAVING A HYDROXYL GROUP ON THE PHENANTHRENE RING THEREOF, PREPARATION METHOD AND USE THEREOF
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Paragraph 0148-0149; 0152, (2017/07/01)
A phenanthroindolizidine and phenanthroquinolizidine alkaloid having a hydroxyl group on the phenanthrene ring thereof was synthesized, which exhibits potent activity as an anticancer agent against, such as breast cancer, lung cancer, and prostate cancer.
Cyano Group Removal from Cyano-Promoted Aza-Diels-Alder Adducts: Synthesis and Structure-Activity Relationship of Phenanthroindolizidines and Phenanthroquinolizidines
Chang, Chi-Fen,Li, Chien-Fu,Tsai, Chia-Chen,Chuang, Ta-Hsien
supporting information, p. 638 - 641 (2016/03/01)
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. (Chemical Equation Presented).
Phenanthroindolizidine and Related Alkaloids: Synthesis of Tylophorine, Septicine, and Deoxytylophorinine
Cragg, John E.,Herbert, Richard B.,Jackson, Frederick B.,Moody, Christopher J.,Nicolson, Ian T.
, p. 2477 - 2486 (2007/10/02)
Tylophorine (1) is synthesized in two ways.The first method begins with the synthesis of the amide-ester (7), which on reaction, successively, with triethyloxonium fluoroborate and sodium borohydride, gives the aminoester (8) selectively; hydrolysis and polyphosphoric acid-catalysed ring-closure of compound (9) gives the ketone (10) which yields tylophorine (1) on Clemmensen reduction.An alternative approach is by a biogenetically patterned sequence which involves condensation of (3,4-dimethoxybenzoyl)acetic acid (26) with 1-pyrroline (24) generated either in situ from putrescine by pea-seedling diamine oxidase or from ornithine by oxidation with N-bromosuccinimide; the product (16) condenses with 3,4-dimethoxyphenylacetaldehyde in benzene to give an enamine .This undergoes cyclisation and dehydration in methanol; sodium borohydride reduction then gives the alkaloid septicine (19) which, on oxidation with thallium(III) trifluoroacetate, yields tylophorine (1).Deoxytylophorinine (34) is made in an exactly analogous manner to the latter method for tylophorine.
