Design, synthesis, docking, and antidepressant activity evaluation of isatin derivatives bearing Schiff bases

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MESRIPOUR AZADEH; JAFARI ELHAM; Hajibeiki Mohammad Reza; HASSANZADEH FARSHID

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Journal Paper

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Journal: Iranian Journal of Basic Medical Sciences Year:2023 | Volume:26 | Issue:4 Page(s): 438-444

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Title

Design, synthesis, docking, and antidepressant activity evaluation of isatin derivatives bearing Schiff bases

Author(s)

MESRIPOUR AZADEH | JAFARI ELHAM | Hajibeiki Mohammad Reza | HASSANZADEH FARSHID | Issue Writer Certificate

Keywords

Antidepressive agents

Inhibitors

Isatin

Monoamine oxidase

Obsessive-compulsive-disorder

Schiff-base

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. 2-(Benzyloxy) benzohydrazide derivatives were synthesized by treating methyl2-hydroxybenzoate with benzyl bromide or 4-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 2-(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 8b and 8e in both doses, and 8 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-11. 01 kcal/mol for compound 8e. Conclusion: N-Benzylated-Isatin (8b, 8e) and N-acetic acid ethyl ester-Isatin derivatives (8c) showed more effective antidepressant activity compared with N-phenyl acetamide Isatin derivatives. Docking results relatively confirm the pharmacological results.

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APA: Copy

MESRIPOUR, AZADEH, JAFARI, ELHAM, Hajibeiki, Mohammad Reza, & HASSANZADEH, FARSHID. (2023). Design, synthesis, docking, and antidepressant activity evaluation of isatin derivatives bearing Schiff bases. IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES, 26(4), 438-444. SID. https://sid.ir/paper/1085298/en

Vancouver: Copy

MESRIPOUR AZADEH, JAFARI ELHAM, Hajibeiki Mohammad Reza, HASSANZADEH FARSHID. Design, synthesis, docking, and antidepressant activity evaluation of isatin derivatives bearing Schiff bases. IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES[Internet]. 2023;26(4):438-444. Available from: https://sid.ir/paper/1085298/en

IEEE: Copy

AZADEH MESRIPOUR, ELHAM JAFARI, Mohammad Reza Hajibeiki, and FARSHID HASSANZADEH, “Design, synthesis, docking, and antidepressant activity evaluation of isatin derivatives bearing Schiff bases,” IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES, vol. 26, no. 4, pp. 438–444, 2023, [Online]. Available: https://sid.ir/paper/1085298/en

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