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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Multicomponent Reactions for Integrating Multiple Functional Groups into an Antioxidant.

Zai-Qun Liu1

  • 1Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, 130021, People's Republic of China.

Chemical Record (New York, N.Y.)
|October 16, 2020
PubMed
Summary
This summary is machine-generated.

Multicomponent reactions (MCRs) efficiently synthesize multifunctional antioxidants to combat oxidative stress and disease. These reactions create complex molecules with improved bioavailability and reduced cytotoxicity for therapeutic applications.

Keywords:
DNA oxidation.antioxidantfree-radical-scavenging propertymulticomponent reaction

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Biochemistry

Background:

  • Oxidative damage to biomolecules is linked to various diseases.
  • Synthetic antioxidants face challenges with bioavailability and cytotoxicity.
  • Developing multifunctional antioxidants with enhanced properties is crucial.

Purpose of the Study:

  • To explore the application of multicomponent reactions (MCRs) for synthesizing novel multifunctional antioxidants.
  • To evaluate the antioxidative efficacy of MCR-derived compounds against radical-induced DNA oxidation.

Main Methods:

  • Utilized Biginelli, Povarov, Groebke, Knoevenagel-related, Ugi, and Passerini multicomponent reactions.
  • Synthesized diverse molecular scaffolds including dihydropyrimidines, quinolines, imidazo[1,2-a]pyridines, and dipeptides.
  • Assessed antioxidative effects using radical-induced DNA oxidation models.

Main Results:

  • Biginelli reaction yielded dihydropyrimidines with antioxidant properties via tautomerization.
  • Povarov and Groebke reactions incorporated multiple antioxidant moieties (ferrocenyl, -N(CH3)2) into complex scaffolds.
  • Ugi and Passerini reactions facilitated the integration of aliphatic chains for enhanced antioxidant features.

Conclusions:

  • MCRs are powerful tools for constructing multifunctional antioxidants with tailored properties.
  • MCR-derived compounds show promise in addressing the limitations of current synthetic antioxidants.
  • This approach offers a versatile strategy for developing novel antioxidants to combat oxidative stress in biological systems.