Design, synthesis, docking, and antidepressant activity evaluation of isatin derivatives bearing Schiff bases
Publish place: Iranian Journal of Basic Medical Sciences، Vol: 26، Issue: 4
Publish Year: 1402
نوع سند: مقاله ژورنالی
زبان: English
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شناسه ملی سند علمی:
JR_IJBMS-26-4_009
تاریخ نمایه سازی: 9 اسفند 1401
Abstract:
Objective(s): Depression is a prevalent psychiatric disorder. Treatment of depression is still a challenge due to the lack of response of some patients to a variety of available medications and side effects. Isatin is an interesting molecule with diversified biological effects. It also participates in many synthetic reactions, as a precursor molecule. In this study, a new series of N-alkyl and N-benzyl isatin derivatives bearing Schiff bases were synthesized and screened for antidepressant activities in mice.Materials and Methods: The synthesis was initiated by N-alkylation and N-benzylation of isatin by an alkylation reaction to give N-substituted isatins. ۲-(Benzyloxy) benzohydrazide derivatives were synthesized by treating methyl۲-hydroxybenzoate with benzyl bromide or ۴-chlorobenzyl bromide which was followed by a reaction with hydrazine hydrate to provide acid hydrazide derivatives. The final compounds were obtained by condensation of N-substituted isatins with ۲-(benzyloxy) benzohydrazide derivatives as Shiff-base products. Compounds were evaluated for antidepressant activities in mice by the locomotor activity, marble burying test, and forced swimming test. Monoamine oxidase–A (MAO–A) enzyme has been used for molecular docking studies.Results: Compounds ۸b and ۸e in both doses, and ۸ c in the lower dose, reduced immobility time during the forced swimming test relative to the control group. All preparations reduced the number of marbles buried compared with the control group. The highest docking score was -۱۱.۰۱ kcal/mol for compound ۸e.Conclusion: N-Benzylated-isatin (۸b, ۸e) and N- acetic acid ethyl ester -isatin derivatives (۸c) showed more effective antidepressant activity compared with N-phenyl acetamide isatin derivatives. Docking results relatively confirm the pharmacological results.
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Authors
Azadeh Mesripour
Department of Pharmacology and Toxicology, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran
Elham Jafari
Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran
Mohamad Reza Hajibeiki
Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran
Farshid Hassanzadeh
Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran
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