Design, synthesis, and biological evaluation of oxindole derivatives as antidepressive agents

Sharad Kumar Suthar; Sumit Bansal; Md Maqusood Alam; Varun Jaiswal; Amit Tiwari; Anil Chaudhary; Angel Treasa Alex; Alex Joseph

doi:10.1016/j.bmcl.2015.09.048

Design, synthesis, and biological evaluation of oxindole derivatives as antidepressive agents

Sharad Kumar Suthar, Sumit Bansal, Md Maqusood Alam, Varun Jaiswal, Amit Tiwari, Anil Chaudhary, Angel Treasa Alex, Alex Joseph

Department of Pharmaceutical Biotechnology, Manipal College of Pharmaceutical Sciences, Manipal
Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

The 3-substituted oxindole derivatives were designed, synthesized, and evaluated for antidepressant activity by employing forced swimming test, tail suspension test, and MAO-A inhibition assay. Results of biological studies revealed that the majority of compounds exhibited potent to moderately potent activity and among them, 12 displayed potency comparable to that of the imipramine with %DID of 37.95 and 44.84 in the FST and TST, respectively. At the same time, imipramine showed %DID of 43.62 and 50.64 in the FST and TST, correspondingly. In the MAO-A inhibition assay, 12 showed an IC₅₀ of 18.27 μmol, whereas the reference drug moclobemide displayed an IC₅₀ of 13.1 μmol. The SAR study disclosed that the presence of bromo atom at the phenyl/furanyl or thienyl moiety in the oxindole derivatives was critical for the antidepressant activity.

Original language	English
Pages (from-to)	5281-5285
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	22
DOIs	https://doi.org/10.1016/j.bmcl.2015.09.048
Publication status	Published - 15-11-2015

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2015.09.048

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title = "Design, synthesis, and biological evaluation of oxindole derivatives as antidepressive agents",

abstract = "The 3-substituted oxindole derivatives were designed, synthesized, and evaluated for antidepressant activity by employing forced swimming test, tail suspension test, and MAO-A inhibition assay. Results of biological studies revealed that the majority of compounds exhibited potent to moderately potent activity and among them, 12 displayed potency comparable to that of the imipramine with %DID of 37.95 and 44.84 in the FST and TST, respectively. At the same time, imipramine showed %DID of 43.62 and 50.64 in the FST and TST, correspondingly. In the MAO-A inhibition assay, 12 showed an IC50 of 18.27 μmol, whereas the reference drug moclobemide displayed an IC50 of 13.1 μmol. The SAR study disclosed that the presence of bromo atom at the phenyl/furanyl or thienyl moiety in the oxindole derivatives was critical for the antidepressant activity.",

author = "Suthar, {Sharad Kumar} and Sumit Bansal and Alam, {Md Maqusood} and Varun Jaiswal and Amit Tiwari and Anil Chaudhary and Alex, {Angel Treasa} and Alex Joseph",

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doi = "10.1016/j.bmcl.2015.09.048",

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AU - Suthar, Sharad Kumar

AU - Bansal, Sumit

AU - Alam, Md Maqusood

AU - Jaiswal, Varun

AU - Tiwari, Amit

AU - Chaudhary, Anil

AU - Alex, Angel Treasa

AU - Joseph, Alex

PY - 2015/11/15

Y1 - 2015/11/15

N2 - The 3-substituted oxindole derivatives were designed, synthesized, and evaluated for antidepressant activity by employing forced swimming test, tail suspension test, and MAO-A inhibition assay. Results of biological studies revealed that the majority of compounds exhibited potent to moderately potent activity and among them, 12 displayed potency comparable to that of the imipramine with %DID of 37.95 and 44.84 in the FST and TST, respectively. At the same time, imipramine showed %DID of 43.62 and 50.64 in the FST and TST, correspondingly. In the MAO-A inhibition assay, 12 showed an IC50 of 18.27 μmol, whereas the reference drug moclobemide displayed an IC50 of 13.1 μmol. The SAR study disclosed that the presence of bromo atom at the phenyl/furanyl or thienyl moiety in the oxindole derivatives was critical for the antidepressant activity.

AB - The 3-substituted oxindole derivatives were designed, synthesized, and evaluated for antidepressant activity by employing forced swimming test, tail suspension test, and MAO-A inhibition assay. Results of biological studies revealed that the majority of compounds exhibited potent to moderately potent activity and among them, 12 displayed potency comparable to that of the imipramine with %DID of 37.95 and 44.84 in the FST and TST, respectively. At the same time, imipramine showed %DID of 43.62 and 50.64 in the FST and TST, correspondingly. In the MAO-A inhibition assay, 12 showed an IC50 of 18.27 μmol, whereas the reference drug moclobemide displayed an IC50 of 13.1 μmol. The SAR study disclosed that the presence of bromo atom at the phenyl/furanyl or thienyl moiety in the oxindole derivatives was critical for the antidepressant activity.

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Design, synthesis, and biological evaluation of oxindole derivatives as antidepressive agents

Abstract

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