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Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

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Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
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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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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 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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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Phenacetin[3]Arenes: Mannich-Type Macrocyclization, Unique Structure, Versatile Functionalization, and Strong

Yanling Shen1, Xiaotong Liang1, Tianning Ma1

  • 1Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610064, China.

Angewandte Chemie (International Ed. in English)
|May 3, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a new macrocyclization method using phenacetin and formaldehyde to create unique hourglass-shaped molecules. These molecules show allosteric behavior and can sense chirality, offering versatile applications in chemistry.

Keywords:
Amide‐based macrocycleHost–guest bindingMannich reactionOne‐pot macrocyclizationPhenacetin[3]arene

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Conventional macrocyclic arene synthesis often relies on CAr-CH2-CAr linkages.
  • Novel synthetic pathways are needed to create macrocycles with unique architectures and functionalities.

Purpose of the Study:

  • To introduce a new NAm-CH2-CAr macrocyclization pathway.
  • To synthesize and characterize phenacetin[3]arenes (Ph[3]s) with unsymmetrical structures.
  • To investigate the host-guest complexation and allosteric behavior of the synthesized macrocycles.

Main Methods:

  • One-pot condensation of phenacetin and its homologs with formaldehyde.
  • Structural characterization using spectroscopic techniques.
  • Host-guest binding studies with organic ammonium guests.
  • Chirality sensing experiments with chiral guests.

Main Results:

  • Phenacetin[3]arenes (Ph[3]s) were synthesized in yields up to 25.9%.
  • Ph[3]s exhibit an unsymmetrical hourglass shape with distinct upper (amide) and lower (alkoxybenzene) rims.
  • Stepwise host-guest complexation (1:1 to 1:2) was observed, leading to allosteric conformational changes (C3 to F conformer).
  • Binding constants for 1:1 and 1:2 complexes were determined (10^4-10^5 M^-1 and >10^6 M^-2, respectively).
  • Selective interactions with chiral guests induced chiroptical responses, enabling chirality sensing.

Conclusions:

  • The novel NAm-CH2-CAr macrocyclization pathway provides access to unique molecular architectures.
  • Phenacetin[3]arenes display tunable host-guest properties and allosteric behavior.
  • The developed macrocycles are promising for applications in chirality sensing and advanced materials due to their functional flexibility.