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Microwave‐Assisted Synthesis of Pyridophenoxazinones, a Class of Antiproliferative Compounds
Author(s) -
De Nisco Mauro,
Bolognese Adele,
Sala Marina,
Pedatella Silvana,
Manfra Michele
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600316
Subject(s) - quinoline , structural isomer , chemistry , combinatorial chemistry , microwave irradiation , functional group , stereochemistry , medicinal chemistry , organic chemistry , catalysis , polymer
Microwave (MW) irradiation allows to prepare a mini‐library of pyridophenoxazinone derivatives, that are crucial intermediates in the synthesis of new antiproliferative compounds, active for human lymphoma/leukemia. The optimized procedure, consisting of a continuous input power of 50 W (80 °C) and a reaction time of 30 min, leads in very satisfactory yields to both regioisomers 5 H ‐pyrido[2,3‐ a ]phenoxazin‐5‐ones and isomeric 5 H ‐pyrido[3,2‐ a ]phenoxazin‐5‐ones, starting from readily available quinoline‐5,8‐dione and substituted 2‐aminophenols (APhOHs). Broad functional group tolerance was observed. The availability of derivatives carrying a carboxyl group at the C‐9 and C‐10 positions enables the synthesis of a new family of 5 H ‐pyridophenoxazin‐5‐one conjugates that were shown to exhibit good anti‐cancer activity.