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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

5.6K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
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Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

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The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
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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.
10.7K

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Two dimers generated by lithospermic decarboxylation coupling from Danshen.

Quan-Chang Gu1, Xiao-Li Wei1, Qing Ji1

  • 1State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Peking Union Medical College and Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing 100050, China.

Bioorganic Chemistry
|August 5, 2022
PubMed
Summary
This summary is machine-generated.

Researchers discovered two new compounds from Danshen (Salvia miltiorrhiza) that inhibit cardiac fibroblast proliferation by targeting MMP9, potentially offering new treatments for heart conditions.

Keywords:
Cardiac fibrosisDecarboxylation couplingLithospermic acid derivativesMMP9Salvia miltiorrhizaStructure elucidation

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Area of Science:

  • Natural Product Chemistry
  • Cardiovascular Pharmacology
  • Molecular Biology

Background:

  • Danshen (Salvia miltiorrhiza) is a traditional Chinese medicine with known cardiovascular benefits.
  • Identifying active compounds in herbal medicines is crucial for drug discovery.
  • Cardiac fibroblasts play a key role in cardiac remodeling and disease progression.

Purpose of the Study:

  • To isolate and characterize new active chemical constituents from Salvia miltiorrhiza.
  • To investigate the biological activity of isolated compounds on cardiac fibroblasts.
  • To elucidate the molecular mechanism underlying the observed biological effects.

Main Methods:

  • Systematic chemical investigation of Salvia miltiorrhiza rhizomes using chromatographic techniques.
  • Structure elucidation of new compounds using comprehensive spectroscopic methods (NMR, MS, IR, UV, ECD).
  • In vitro biological assays using isoproterenol-induced cardiac fibroblasts (AC16 cells) to assess proliferation, migration, and activation, with MMP9 expression analysis.

Main Results:

  • Two novel lithospermic acid derivatives (compounds 1 and 2) and five known phenylpropionic acids were isolated.
  • Compound 1 demonstrated significant inhibition of cardiac fibroblast proliferation.
  • Compound 1 was identified as a likely inhibitor of matrix metalloproteinase 9 (MMP9), reversing its increased expression and alleviating fibroblast migration and activation in ISO-treated cells.

Conclusions:

  • Compound 1, a new lithospermic acid derivative from Salvia miltiorrhiza, possesses potent anti-fibrotic properties.
  • The anti-fibrotic effects of compound 1 are mediated through the inhibition of MMP9.
  • These findings highlight the therapeutic potential of compound 1 for treating cardiovascular diseases involving cardiac fibrosis.