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Halo-Substituted Adamantyl Benzamides as Digestive Enzyme Modulators: Synthesis, DFT Analysis, and Biological
Mahesh Kumar Purohit1, Anjaneyulu Bendi2, Prabhjot Kaur3
1Department of Chemistry, Veer Surendra Sai University of Technology, Sambalpur, India.
Chemistry & Biodiversity
|July 8, 2026
Summary
Novel adamantane benzamides show potential in drug discovery due to favorable metabolic stability and pharmacological properties. In silico and in vitro studies confirm their drug-likeness and enzyme interactions, particularly the fluoro-substituted derivative.
Area of Science:
- Medicinal Chemistry
- Computational Chemistry
- Pharmacology
Background:
- Adamantane benzamides are emerging scaffolds in drug discovery.
- Predicting metabolic stability, pharmacological potential, and lipophilicity is crucial for drug development.
Purpose of the Study:
- To synthesize novel para-halo substituted adamantane benzamides.
- To evaluate their drug-likeness, pharmacokinetic profiles, and interactions with digestive enzymes using in silico and in vitro methods.
Main Methods:
- Synthesis via acylation of adamantaminol with p-halo substituted benzoyl chlorides.
- Characterization using spectroscopic methods.
- In silico studies including DFT for energy gap analysis, ADME predictions, and molecular docking.
- In vitro enzyme inhibition and activation assays.
Main Results:
- High yields achieved in synthesis; spectroscopic characterization confirmed product identity.
- DFT studies showed a consistent HOMO-LUMO energy gap of approximately 5.4 eV for all novel compounds.
- ADME assessments indicated good physicochemical properties, blood-brain barrier permeability, high gastrointestinal absorption, and low toxicity.
- The fluoro-substituted benzamide exhibited potent inhibition of pepsin (IC50 = 2.51 ± 1.4) and trypsin (IC50 = 3.8 ± 1.2), and significant activation of lipase (60.18 ± 1.6%) and α-amylase (57.66 ± 1.5%).
Conclusions:
- Novel para-halo substituted adamantane benzamides are promising scaffolds for drug discovery.
- The fluoro-substituted derivative demonstrates significant potential as a therapeutic agent due to its enzyme modulation properties and favorable pharmacokinetic profile.
