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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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Base-Catalyzed Ring-Opening of Epoxides02:26

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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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Preparation of Epoxides03:00

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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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Structure and Nomenclature of Epoxides02:38

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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Prodrugs

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Prodrugs are a class of pharmaceutical compounds that undergo a biotransformation process within the body to be converted into a pharmacologically active drug. Prodrugs are designed to improve the therapeutic properties of the parent drug, such as enhancing bioavailability, increasing stability, or reducing toxicity. The concept of prodrugs revolves around modifying the chemical structure of the original drug to make it more effective or convenient for administration.
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Epoxides: Developability as active pharmaceutical ingredients and biochemical probes.

Baljit Kaur1, Palwinder Singh1

  • 1Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, India.

Bioorganic Chemistry
|May 18, 2022
PubMed
Summary

This study reviews epoxide compounds in medicine and biochemical probes, highlighting strategies for developing these reactive molecules in drug discovery despite associated challenges.

Keywords:
Biochemistry and pharmacology of epoxide-based drugsEpoxide functional groupEpoxide in metabolic pathwaysEpoxide-based drugs

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Biochemistry

Background:

  • Epoxide functional groups are present in numerous natural and synthetic compounds.
  • Epoxides play roles in drug efficacy and serve as molecular tools.
  • Concerns exist regarding the reactivity of the epoxide functional group.

Purpose of the Study:

  • To compile information on epoxide-based medicinal compounds and biochemical probes.
  • To analyze the advantages and challenges associated with the epoxide functional group.
  • To examine strategies for successful development of epoxide-based compounds in drug discovery.

Main Methods:

  • Literature review of epoxide-based medicinal compounds.
  • Analysis of biochemical probes utilizing epoxide moieties.
  • Examination of drug discovery programs involving epoxide compounds.

Main Results:

  • Identified diverse applications of epoxides in medicinal chemistry.
  • Highlighted the dual nature of epoxide reactivity: beneficial in targeted therapies but challenging in development.
  • Documented various synthetic and strategic approaches to manage epoxide reactivity.

Conclusions:

  • Epoxide-based compounds offer significant therapeutic potential.
  • Careful strategic planning is crucial for overcoming the reactivity challenges of epoxides in drug development.
  • Further research into epoxide chemistry can unlock new avenues in drug discovery.