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Synthesis and Evaluation of the Cytotoxicities of Neoflavenes
Author(s) -
Li SieRong,
Chen HsingMing,
Chen PoYuan,
Tsai JuiChi,
Chen LiangYeu,
Wang EngChi,
Huang YiTing,
Wei YunChen,
Lu PeiJung
Publication year - 2008
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200800137
Subject(s) - chemistry , yield (engineering) , wittig reaction , mammary carcinoma , grignard reaction , ring closing metathesis , stereochemistry , in vitro , combinatorial chemistry , metathesis , medicinal chemistry , organic chemistry , carcinoma , biochemistry , metallurgy , medicine , materials science , reagent , polymerization , polymer
The synthesis of neoflavene and neoflavenes with methoxy substituents at different positions are described. As starting materials, various salicylaldehydes were run through sequential reactions such as O ‐allylation, Grignard reaction, oxidation, Wittig reaction, and ring‐closing metathesis to yield the target neoflavenes in good yield. Among the prepared neoflavenes, 7‐methoxy‐4′‐methoxyneoflavene ( 6e ) and 8‐methoxy‐4′‐methoxyneoflavene ( 6f ) exhibiting potential cell toxicities against various cells were disclosed. In particular, 6f which exhibited an IC 50 value of 6.5 ± 2.0 and 5.1 ± 1.1 μM against gastric carcinoma and lung carcinoma cells in vitro was found, respectively. Meanwhile, the structure and activity relationship of our synthesized neoflavenes is further discussed briefly.