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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
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Authors Affiliations
  1. 1. Faculty of Pharmacy, International Campus (TUMS-IC), Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
  6. 6. Department of Cellular Biotechnology at Cell Science Research Center, Royan Institute for Biotechnology, ACECR, Isfahan, Iran
  7. 7. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  8. 8. Department of Pharmacology, School of Medicine TUMS-IC, Tehran, Iran
  9. 9. Department of Medicinal Chemistry, Faculty of Pharmacy and Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

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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