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Volume 21, Issue 15
  • ISSN: 1570-1808
  • E-ISSN: 1875-628X

Abstract

Aims

Synthesis of novel 4-bromobenzoic acid-based hydrazone-Schiff base derivatives and to screen them for their α-amylase inhibitory activity.

Background

The most often employed organic compounds are derivatives of the hydrazone-Schiff base. Numerous biological actions, such as antipyretic, antiviral, anti-inflammatory, anti-proliferative, anti-malarial, antibacterial, and anti-fungal ones, have been linked to them.

Objective

The biological activities of hydrazone-Schiff base compounds encouraged us to evaluate the synthesized derivatives for inhibition activity against the α-amylase enzyme.

Methods

In current research work twenty-nine Schiff base derivatives of 4-bromobenzoic acid were synthesized in worthy yields by treating various replaced aldehydes with 4-bromobenzohydrazide using methanol solvent in catalytic quantity of acetic acid. The products were structurally described through the support of several spectroscopic methods (EI-MS and 1H-NMR) and finally evaluated against α-amylase enzyme.

Results

All the made derivatives exhibited worthy inhibition potential from IC = 0.21 ± 0.01 to 5.50 ± 0.01 M when to the usual acarbose drug having IC = 1.34 ± 0.01 M. Compound (IC = 0.21 ± 0.01 M) was established as the most active inhibitor among the series better than standard. The structure-activity relationship study showed that the alteration in the activity of the produced products might be due to the attached position and nature of the substituents. Furthermore, study supported the effects of groups attached on the binding interaction with α-amylase enzyme.

Conclusion

A series of substituted hydrazone Schiff bases based on 4-bromobenzoic acid were produced, confirmed the structures by EI-MS and 1H-NMR spectroscopic methods and lastly tested for their α-amylase inhibitory potential. Among the series, twenty-four products indicated brilliant inhibition potential having IC values from 0.21 ± 0.01 to 1.30 ± 0.01 M. The structure-activity relationship study showed that the alteration in the activity of the synthesized products might be due to the attached position and nature of the substituents. On the other hand, studies advocated that the synthesized Schiff base derivatives have prevalent interactions of binding within the active site of the α-amylase enzyme, and because of their various attached substituent, their conformation is altered in the active site of the enzyme. The current study recognized a number of lead candidates derived from 4-bromobenzoic acid. Additional investigation of the synthesized derivatives for coming research to get novel α-amylase inhibitors.

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2024-01-10
2024-12-29

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Synthesis of Some Novel 4-bromobenzoic Acid Clubbed Hydrazone Schiff Base Derivatives as Potent α-amylase Inhibitors: In vitro and In silico Studies
Letters in Drug Design & Discovery 21, 3186 (2024); https://doi.org/10.2174/0115701808262821231114114237
/content/journals/lddd/10.2174/0115701808262821231114114237
/content/journals/lddd/10.2174/0115701808262821231114114237
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  • Article Type:     Research Article
Keyword(s): 4-bromobenzoic acid; and molecular docking study; in-vitro; structure activity relationship; Synthesis; α-amylase inhibition

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