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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Structure and Nomenclature of Thiols and Sulfides02:17

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Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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TGF - β Signaling Pathway01:16

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The TGF-β signaling pathway regulates cell growth, differentiation, adhesion, motility, and development. TGF-β ligands that induce TGF-β signaling are synthesized in their latent form. Several proteases or cell surface receptors such as integrins act upon the latent form, releasing the active ligand. There are three types of mammalian TGF-βs: (TGF-β1, TGF-β2, and TGF-β3) that bind as homodimers or heterodimers to TGF-β receptors. The TGF-β receptors...
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Adrenergic Receptors: β Subtype01:26

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β-adrenoceptors have varied sensitivities towards adrenaline, noradrenaline, and isoprenaline. The order of agonist potency is as follows:
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β1-adrenoceptors: β1-adrenoceptors...
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Antianginal Drugs: Nitrates and β-Blockers01:16

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In cardiovascular health, antianginal drugs combat angina pectoris — a condition marked by chest pain owing to diminished blood flow to the heart.
Organic nitrates,  such as nitroglycerin, play a pivotal role. Once metabolized, they liberate nitric oxide, a molecular marvel. Nitric oxide triggers guanylyl cyclase and augments cGMP production. This biochemical cascade orchestrates the relaxation of vascular smooth muscles, ushering in vasodilation and enhancing coronary blood flow....
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β-Hydroxy sulfides and their syntheses.

Mokgethwa Bruce Marakalala1, Edwin M Mmutlane1, Henok H Kinfe1

  • 1Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park 2006, South Africa.

Beilstein Journal of Organic Chemistry
|July 18, 2018
PubMed
Summary
This summary is machine-generated.

Marine organisms are rich sources of sulfur-containing natural products. This review explores beta-hydroxy sulfides, their natural occurrence, synthesis, and use in complex molecule construction.

Keywords:
alkene thiofunctionalizationepoxide thiolysissulfur-containing natural productsβ-hydroxy sulfides

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Area of Science:

  • Natural Product Chemistry
  • Organic Synthesis
  • Marine Biology

Background:

  • Sulfur-containing natural products are widespread, with marine organisms being a primary source.
  • Sulfur exists in various forms and oxidation states within these natural compounds.
  • Marine environments contain abundant sulfate ions, contributing to the prevalence of sulfur compounds.

Purpose of the Study:

  • To review beta-hydroxy sulfides and their analogs in natural products.
  • To outline general synthetic protocols for these compounds.
  • To showcase applications in target-oriented synthesis.

Main Methods:

  • Literature review of natural product chemistry.
  • Analysis of synthetic methodologies for beta-hydroxy sulfides.
  • Case studies of synthetic applications.

Main Results:

  • Identification of diverse natural products containing beta-hydroxy sulfide motifs.
  • Compilation of established and novel synthetic routes.
  • Demonstration of utility in synthesizing complex molecules.

Conclusions:

  • Beta-hydroxy sulfides are significant structural units in natural products.
  • Efficient synthetic strategies are available for their preparation.
  • These compounds serve as valuable building blocks in organic synthesis.