oxidative aromatization, cytotoxic activity evaluation and conformational study of novel 7-aryl-10, 11-dihydro-7h-chromeno [4, 3-b]quinoline-6, 8(9h, 12h)-dione derivatives

Authors

radineh motamedi department of chemistry, payame noor university, delijan, iran

abbas shafiee pharmaceutical sciences research center, faculty of pharmacy, tehran university of medical sciences, tehran 14174, iran.

mohammad reza rezai department of chemistry, payame noor university, delijan, iran.

omidreza firuzi medicinal & natural products chemistry research center, shiraz university of medical, sciences, shiraz, iran

abstract

in the present work, novel 7-aryl-10, 11-dihydro-7h-chromeno [4, 3-b]quinoline-6, 8(9h, 12h)-dione derivatives were synthesized by oxidation of 7-aryl-8, 9, 10, 12-tetrahydro-7h-chromeno[4, 3-b]quinoline-6, 8-diones in the presence of silica sulfuric acid/nano2 with yields of 64-74%. cytotoxic activity of synthesized compounds was assessed on three different human cancer cell lines (k562, ls180, and mcf-7). synthesized compounds showed moderate cytotoxic activities. the most active one apeared to be 2e, containing a methoxy group on the meta position of phenyl ring (ic50 range in different cell lines: 11.1–55.7 µm). furthermore; comparison of the cytotoxic activity of these novel oxidized derivatives with non-oxidized counterparts revealed that oxidation of dihydropyridine ring to pyridine, improves the activity especially in ls180 cell line. conformational analysis revealed that some conformational aspects of oxidized derivatives such as orientation of c7-aryl substitute were clearly different from non-oxidized ones.

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Journal title:

iranian journal of pharmaceutical research

جلد ۱۳، شماره ۱، صفحات ۱۰۳-۱۱۴

Keywords

[ ' o x i d a t i v e a r o m a t i z a t i o n ' , ' c h r o m e n o [ 4 ' , 3 , ' b ] q u i n o l i n e ' , ' c y t o t o x i c i t y ' , ' c o n f o r m a t i o n a l a n a l y s i s ' ]

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