(2016) Hetero-annulated coumarins as new AChE/BuChE inhibitors: synthesis and biological evaluation. Medicinal Chemistry Research. pp. 1831-1841.
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Abstract
A series of chromene-fused coumarins known as 10,11-dihydrochromeno4,3-bchromene-6,8(7H,9H)-diones 4a�o were synthesized through one-pot reaction of appropriate benzaldehydes, dimedone, and 4-hydroxycoumarin in the presence of nano-silica sulfuric acid under solvent-free condition in good yields. The in vitro anticholinesterase assay revealed that the 3-hydroxyphenyl analog 4e showed the highest inhibitory activity against both acetylcholinesterase and butyrylcholinesterase, possessing IC50 values of 3.28 and 2.19 �µM, respectively. The structure-activity relationships study demonstrated that the selectivity for acetylcholinesterase over butyrylcholinesterase could be modulated by introducing second hydroxyl or methoxy substituent on the para-position of the 3-hydroxyphenyl pendent group. The docking study of compound 4e with acetylcholinesterase confirmed ��� stacking interaction between the coumarin moiety and Trp279 as well as the formation of hydrogen bonding between hydroxyl group and Asn85. �© 2016, Springer Science+Business Media New York.
| Item Type: | Article |
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| Keywords: | 10,10 dimethyl 7 (3 nitrophenyl) 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 10,10 dimethyl 7 (4 nitrophenyl) 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 10,10 dimethyl 7 (p tolyl) 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 10,10 dimethyl 7 phenyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (2 chlorophenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (2,4 dichlorophenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (3 bromophenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (3 fluorophenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (3 hydroxy 4 methoxyphenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (3 hydroxyphenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (3,4 dihydroxyphenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (3,4 dimethoxyphenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (4 fluorophenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (4 hydroxyphenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; 7 (4 methoxyphenyl) 10,10 dimethyl 7,9,10,11 tetrahydro 6h,8h chromeno4,3 bchromene 6,8 dione; cholinesterase inhibitor; coumarin derivative; tacrine; unclassified drug, Article; carbon nuclear magnetic resonance; cholinesterase inhibition; comparative study; drug screening; drug synthesis; enantiomer; enzyme active site; enzyme assay; hydrogen bond; IC50; in vitro study; molecular docking; proton nuclear magnetic resonance; structure activity relation |
| Page Range: | pp. 1831-1841 |
| Journal or Publication Title: | Medicinal Chemistry Research |
| Volume: | 25 |
| Number: | 9 |
| Publisher: | Birkhauser Boston |
| Depositing User: | ms soheila Bazm |
| URI: | http://eprints.ssu.ac.ir/id/eprint/9717 |
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