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N ‐(Substituted benzyl)‐3,5‐bis(benzylidene)‐4‐piperidones: Synthesis and Preliminary Anti‐leukemia Activity (I)
Author(s) -
Wang Jing,
Meng Wen,
Ni Zhenjie,
Xue Sijia
Publication year - 2011
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201180365
Subject(s) - chemistry , k562 cells , aldol condensation , hydrolysis , stereochemistry , decarboxylation , leukemia , proton nmr , elemental analysis , condensation reaction , organic chemistry , in vitro , catalysis , biochemistry , medicine
A series of novel N ‐(substituted benzyl)‐3,5‐bis(benzylidene)‐4‐piperidones 5a – 5o were synthesized with substituted benzylamines as raw materials via a series of Michael addition, Dieckmann condensation, hydrolysis decarboxylation and aldol condensation. The structures were confirmed by 1 H NMR, IR, MS techniques and elemental analysis. Assay‐based antiproliferative activity study using leukemic cell lines K562 revealed that most of the title compounds have high effectiveness in inhibiting leukemia K562 cells proliferation, among which the compounds 5g (IC 50 =7.81 µg·mL −1 ), 5k (IC 50 =6.35 µg·mL −1 ), 5l (IC 50 =7.20 µg·mL −1 ), and 5o (IC 50 =5.79 µg·mL −1 ) have better inhibition activities than standard 5‐fluorouracil (IC 50 =8.56 µg·mL −1 ).