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Dopamine receptor antagonists, also known as antipsychotic agents, are critical in managing chemotherapy-induced vomiting. These antiemetic agents block dopamine receptors in the chemoreceptor trigger zone (CTZ), inhibiting signal transmission to the vomiting center. Antipsychotic agents encompass phenothiazines (PTZ), butyrophenones, benzamides, and thienobenzodiazepines (Zyprexa), which are utilized for their antiemetic and sedative properties.
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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...
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Sedatives and hypnotics encompass a wide range of substances, each with its unique mechanism of action, uses, and potential adverse effects.
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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Phenothiazine Embedded Dithiasmaragdyrins.

Neha Tripathi1, Supriti Dutta1, Bharti Yadav1

  • 1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India.

Chemistry, an Asian Journal
|April 25, 2024
PubMed
Summary

Novel phenothiazine-embedded dithiasmaragdyrins were synthesized and characterized. These macrocycles exhibit unique structural and electronic properties, with potential applications in materials science.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Phenothiazine derivatives are known for their diverse electronic and photophysical properties.
  • Macrocyclic compounds offer unique structural frameworks for tuning molecular behavior.

Purpose of the Study:

  • To synthesize and characterize novel phenothiazine-embedded dithiasmaragdyrins.
  • To investigate the structural, spectral, and electrochemical properties of these new macrocycles.

Main Methods:

  • Multi-step organic synthesis involving condensation reactions.
  • Nuclear Magnetic Resonance (NMR) spectroscopy for structural elucidation.
  • UV-Vis absorption spectroscopy and electrochemistry for property analysis.
  • Density Functional Theory (DFT) and Time-Dependent DFT (TD-DFT) for theoretical studies.

Main Results:

  • Successful synthesis of two types of phenothiazine-embedded dithiasmaragdyrins.
  • NMR studies revealed distinct thiophene ring orientations based on the phenothiazine core (sulfone vs. non-sulfone).
  • Both macrocycle types displayed nonaromatic and panchromic absorption features in neutral and protonated states.
  • Electrochemical studies showed phenothiazine-embedded dithiasmaragdyrins are more electron-rich.
  • DFT and TD-DFT studies confirmed distorted structures and supported experimental findings.

Conclusions:

  • The study presents novel phenothiazine-embedded dithiasmaragdyrins with tunable properties.
  • Structural variations significantly influence electronic and spectral characteristics.
  • These findings contribute to the understanding of macrocyclic chemistry and pave the way for new functional materials.