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Preparation of Epoxides03:00

Preparation of Epoxides

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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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Cycloaddition Reactions: Overview01:16

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Phase I Oxidative Reactions: Overview01:19

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Phase I biotransformation, or functionalization, is a crucial chemical process that converts drugs and other xenobiotics into more water-soluble forms, facilitating expulsion from the body. It involves oxidative, reductive, and hydrolytic reactions that add or unveil polar functional groups on lipophilic substrates. Key players in phase I reactions are the mixed-function oxidases. Situated in liver cell microsomes, these enzymes predominantly carry out drug metabolism. They require molecular...
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Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

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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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Oxidation and Reduction of Organic Molecules01:19

Oxidation and Reduction of Organic Molecules

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Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Oxa-spirocycles: synthesis, properties and applications.

Kateryna Fominova1, Taras Diachuk1, Dmitry Granat1

  • 1Enamine Ltd Chervonotkatska 78 02094 Kyiv Ukraine Pavel.Mykhailiuk@gmail.com http://www.enamine.net http://www.mykhailiukchem.org.

Chemical Science
|October 20, 2021
PubMed
Summary

A new method for creating oxa-spirocycles was developed using iodocyclization. These novel compounds show improved solubility and lower lipophilicity, with potent analogues of terazosin showing promise in vivo.

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Drug Discovery

Background:

  • Spirocyclic molecules are important scaffolds in medicinal chemistry.
  • Developing novel synthetic routes to diverse spirocyclic compounds is crucial for drug discovery.
  • Improving physicochemical properties like solubility and lipophilicity is key for drug development.

Purpose of the Study:

  • To develop a general synthetic approach for a new class of spirocyclic molecules, termed oxa-spirocycles.
  • To explore the impact of incorporating an oxygen atom into the spirocyclic core on molecular properties.
  • To synthesize and evaluate oxa-spirocyclic analogues of existing drugs for enhanced therapeutic potential.

Main Methods:

  • Development of a general synthetic strategy centered on iodocyclization.
  • Preparation of a library of over 150 diverse oxa-spirocyclic compounds.
  • In vitro and in vivo studies to assess physicochemical properties and biological activity.

Main Results:

  • A versatile method for synthesizing oxa-spirocycles was established.
  • Incorporation of oxygen significantly enhanced water solubility (up to 40-fold) and reduced lipophilicity.
  • More potent oxa-spirocyclic analogues of the antihypertensive drug terazosin were successfully synthesized and validated in vivo.

Conclusions:

  • The developed iodocyclization approach provides efficient access to novel oxa-spirocycles.
  • Oxa-spirocycles possess favorable physicochemical properties for drug development.
  • This new class of compounds holds potential for the development of improved therapeutics, exemplified by enhanced terazosin analogues.