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Design, Synthesis and Biological Evaluation of Novel Phthalimide-Schiff Base-Coumarin Hybrids As Potent Α-Glucosidase Inhibitors Publisher



Sherafati M1 ; Mohammadikhanaposhtani M2 ; Moradi S1 ; Asgari MS3 ; Najafabadipour N4 ; Faramarzi MA4 ; Mahdavi M5 ; Biglar M5 ; Larijani B5 ; Hamedifar H6 ; Hajimiri MH7
Authors
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Authors Affiliations
  1. 1. Department of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Iran
  2. 2. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  3. 3. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
  4. 4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  6. 6. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
  7. 7. Nano Alvand Company, Avicenna Tech Park, Tehran University of Medical Sciences, Tehran, Iran

Source: Chemical Papers Published:2020


Abstract

We have designed and synthesized phthalimide-Schiff base-coumarin hybrids 8a–b, 9a–d, 10a–b, and 11a–d and evaluated them for α-glucosidase inhibitory potential against yeast form of this enzyme. For the synthesis of title compounds 4-hydroxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 2-hydroxybenzaldehyde, 2-hydroxybenzaldehyde derivatives, coumarin-3-carbohydrazide, and coumarin-7-yloxy-acetohydrazide were used. In vitro α-glucosidase inhibition revealed that all the synthesized compounds exhibited outstanding α-glucosidase inhibition with IC50 values ranging between 85.2 ± 1.7 and 577.7 ± 7.5 µM when compared with the standard inhibitor acarbose having IC50 value 750.0 ± 12.0 µM. The most potent compounds were 4-hydroxybenzaldehyde derivative 8a with coumarin-3-carbohydrazide moiety, 2-hydroxy-5-nitrobenzaldehyde derivative 11d with coumarin-7-yloxy-acetohydrazide moiety, and 2-hydroxy-5-nitrobenzaldehyde derivative 9d with coumarin-3-carbohydrazide moiety. Molecular docking studies were carried out to understand the interaction modes and binding energies of the most active compounds and standard drug acarbose. This studies predicted that compounds 8a, 11d, and 9d (respectively with binding energies = − 10.77, − 8.65, and − 8.66 kcal/mol) bind to active site α-glucosidase more easily than acarbose (binding energy = − 4.04 kcal/mol). © 2020, Institute of Chemistry, Slovak Academy of Sciences.
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