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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
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Epoxy-Functionalized Isatin Derivative: Synthesis, Computational Evaluation, and Antibacterial Analysis.

Deepanjali Shukla1, Iqbal Azad1, Mohd Arsh Khan1

  • 1Department of Chemistry, Integral University, Lucknow 226026, India.

Antibiotics (Basel, Switzerland)
|June 25, 2025
PubMed
Summary

A novel epoxy-functionalized isatin derivative, L3, shows promise as an antibacterial agent targeting DNA adenine methyltransferase (Dam) in multidrug-resistant Klebsiella pneumoniae. Its favorable drug-like properties and binding affinity suggest potential for antimicrobial drug development.

Keywords:
ADMETK. pneumoniaeantibacterialdam proteinepoxy-functionalized isatinmolecular docking

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Area of Science:

  • Medicinal Chemistry
  • Molecular Biology
  • Computational Chemistry

Background:

  • Emergence of multidrug-resistant Klebsiella pneumoniae necessitates novel antibacterial compounds targeting non-classical pathways.
  • DNA adenine methyltransferase (Dam) is an underutilized target for antibiotic development.
  • Epoxy-functionalized isatin derivatives have not been extensively studied as Dam inhibitors.

Purpose of the Study:

  • Synthesize and characterize a novel epoxy-functionalized isatin derivative (L3).
  • Evaluate the antibacterial activity and drug-likeness of L3.
  • Investigate the interaction of L3 with Klebsiella pneumoniae Dam protein.

Main Methods:

  • One-pot synthesis and spectroscopic characterization (FT-IR, NMR, MS, UV-Vis) of L3.
  • In silico ADMET profiling and drug-likeness assessment (Lipinski's rules, QED).
  • Molecular docking studies of L3 against a homology model of K. pneumoniae Dam protein.
  • Minimum Inhibitory Concentration (MIC) assays against selected bacterial strains.

Main Results:

  • L3 demonstrated inhibitory activity against K. pneumoniae with a MIC of 93.75 μg/mL.
  • In silico analysis predicted favorable drug-like properties for L3, including oral bioavailability and BBB permeability.
  • Docking studies revealed significant binding affinity of L3 to K. pneumoniae Dam protein (-6.4 kcal/mol Vina, -4.85 kcal/mol AutoDock), with key hydrogen and Van der Waals interactions.

Conclusions:

  • L3 is a promising scaffold for developing new antimicrobials targeting Dam in K. pneumoniae.
  • The favorable ADMET profile and physicochemical properties of L3 support its potential as a drug candidate.