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Direct-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship01:22

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Cholinergic agonists or cholinomimetics mimic the action of acetylcholine to stimulate the parasympathetic nervous system. They are categorized into direct-acting and indirect-acting agents. The direct-acting cholinergic drugs induce the parasympathetic response by directly binding to the muscarinic or nicotine receptors. In comparison, the indirect-acting cholinergic drugs prevent acetylcholine hydrolysis, indirectly contributing to the extended parasympathetic response.
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Indirect-acting cholinergic agonists are agents that interact with the acetylcholinesterase enzyme in the synaptic cleft, preventing the breakdown of acetylcholine into choline and acetate. Consequently, the concentration of acetylcholine in the synaptic cleft increases. These agonists can be classified into reversible and irreversible inhibitors based on their duration of action.
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Cholinergic Antagonists: Chemistry and Structure-Activity Relationship01:29

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Cholinergic antagonists bind to cholinergic receptors and limit the effects of acetylcholine and other cholinergic agonists. Based on the specific cholinergic receptor affinity, these antagonists are classified as muscarinic or nicotinic. Anticholinergics interrupt parasympathetic innervations while sympathetic innervations remain uninterrupted. Muscarinic antagonists are also called 'muscarinic antagonists', 'antimuscarinics', or 'parasympatholytics'. Nicotinic...
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Direct-Acting Cholinergic Agonists: Pharmacokinetics01:31

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Direct-acting cholinergic agonists, such as synthetic choline esters and naturally occurring alkaloids, exert their effects by enhancing the actions of acetylcholine and stimulating the parasympathetic nervous system. Synthetic choline esters share structural similarities with acetylcholine. For example, they have a positively charged quaternary ammonium or onium group, contributing to their hydrophilic characteristics. As a result, they are poorly absorbed in the body through oral...
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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Indirect-Acting Cholinergic Agonists: Mechanism of Action01:18

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Indirect-acting cholinergic agonists work by interacting with an enzyme called acetylcholinesterase (AChE) in the synaptic cleft. They can be reversible or irreversible inhibitors and have different effects on the enzyme.
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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
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Click-Dimerized Cinchona Alkaloids.

Przemysław J Boratyński1, Rafał Kowalczyk1

  • 1Department of Organic Chemistry, Wrocław University of Technology , Wyspiańskiego 27, Wrocław 50-370, Poland.

The Journal of Organic Chemistry
|August 5, 2016
PubMed
Summary

New Cinchona alkaloid dimers were synthesized using click chemistry. These compounds, featuring bitriazole linkers, effectively transferred chirality in asymmetric copper-catalyzed Michael additions.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Cinchona alkaloids are vital chiral scaffolds in asymmetric synthesis.
  • Click chemistry offers efficient routes to complex molecular architectures.
  • Developing novel chiral ligands is crucial for enantioselective catalysis.

Purpose of the Study:

  • To synthesize novel Cinchona alkaloid-derived dimers.
  • To evaluate these dimers as ligands in asymmetric catalysis.
  • To investigate the role of the linker in chirality transfer.

Main Methods:

  • Copper-catalyzed 1,3-dipolar "click" cycloaddition reactions were employed.
  • Bis(TMS)butadiyne and other bivalent alkynes were used as coupling partners.
  • The synthesized dimers were tested as ligands in asymmetric copper-catalyzed Michael addition reactions.

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Main Results:

  • Cinchona alkaloid dimers were obtained in high yields.
  • The bitriazole-linked dimers demonstrated high efficacy as ligands.
  • Effective chirality transfer was observed, attributed to the linker's presence.

Conclusions:

  • Novel Cinchona alkaloid dimers can be efficiently synthesized via click chemistry.
  • These dimers serve as effective ligands for asymmetric copper-catalyzed reactions.
  • The bitriazole linker plays a critical role in achieving high enantioselectivity.