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Synthesis, Docking Study and Neuroprotective Effects of Some Novel Pyrano[3,2-C]Chromene Derivatives Bearing Morpholine/Phenylpiperazine Moiety Publisher Pubmed



Sameem B1 ; Saeedi M2, 3 ; Mahdavi M4 ; Nadri H5 ; Moghadam FH6 ; Edraki N7 ; Khan MI8 ; Amini M9
Authors

Source: Bioorganic and Medicinal Chemistry Published:2017


Abstract

Novel pyrano[3,2-c]chromene derivatives bearing morpholine/phenylpiperazine moiety were synthesized and evaluated against acetylcholinestrase (AChE) and butylcholinestrase (BuChE). Among the synthesized compounds, N-(3-cyano-4-(4-methoxyphenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromen-2-yl)-2-(4-phenylpiperazin-1-yl)acetamide (6c) exhibited the highest acetylcholinestrase inhibitory (AChEI) activity (IC50 = 1.12 µM) and most of them showed moderate butylcholinestrase inhibitory activity (BChEI). Kinetic study of compound 6c confirmed mixed type of inhibition towards AChE which was in covenant with the results obtained from docking study. Also, it was evaluated against β-secretase which demonstrated low activity (inhibition percentage: 18%). It should be noted that compounds 6c, 7b, 6g, and 7d showed significant neuroprotective effects against H2O2-induced PC12 oxidative stress. © 2017 Elsevier Ltd
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