Synthesis, Structure-Activity Relationship (SAR) Studies on some 4-Aryl-4Hchromenes and Relationship between Lipophilicity and Antitumor Activity
Ahmed M. El-Agrody,
Essam Shawky A. E. H. Khattab,
Ahmed M. Fouda.
Some 4-aryl-4H-chromenes 3a-h, 5a-g, 7a-g and 9a-g were obtained by reaction of 3-substituted phenol 1, 4, 6
and 8 with α-cyanocinnamonitrile derivatives 2. We explored the structure activity relationship (SAR) of 4-aryl-4Hchromenes
with modification at the 4- and 7-positions. The antitumor activity of the synthesized compounds was investigated
in comparison with the standard drugs Vinblastine and Doxorubicin using microculture tetrazolium (MTT) colorimetric assay.
Some compounds were found to have good in vitro antitumor activity. The structure-activity relationship (SAR) study
revealed that the antitumor activity of 4-aryl-4H-chromenes was significantly affected by the lipophilicity, the calculated Log
P value and the balance between 7-hydrophilic or hydrophobic substituent and hydrophobic substituent on the benzene ring at
4-position. The structures of the newly prepared compounds were confirmed by elemental analysis and spectral data.
Keywords: 3-Substituted phenol, antitumor, α-cyanocinnamonitriles, 4-aryl-4H-chromenes, SAR.
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