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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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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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Radical Reactivity: Nucleophilic Radicals01:16

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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Radical Reactivity: Electrophilic Radicals01:02

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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Antidotes are medicinal substances used to counteract the harmful effects of toxins or drugs in the body. They function in various ways, each uniquely designed to combat specific toxic compounds.
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Radical Formation: Elimination00:51

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Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions...
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Development of Next-Generation Antimalarial Acridones with Radical Cure Potential.

Rozalia A Dodean1,2, Yuexin Li2, Xiaowei Zhang2

  • 1Department of Chemistry, Portland State University, Portland, Oregon 97201, United States.

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|April 3, 2025
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Summary
This summary is machine-generated.

New acridone compounds show potent activity against malaria parasites in both blood and liver stages. These next-generation antimalarials offer a promising new treatment option, even against drug-resistant strains.

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Area of Science:

  • Medicinal Chemistry
  • Parasitology
  • Drug Discovery

Background:

  • Previous lead compound T111 showed activity against Plasmodium falciparum asexual blood-stage (ABS) and Plasmodium berghei liver-stage (LS) parasites.
  • Acridone derivatives are being explored for their antimalarial potential.

Purpose of the Study:

  • To systematically design and synthesize next-generation antimalarial acridones.
  • To evaluate their efficacy against both ABS and LS malaria parasites.
  • To assess their safety and metabolic profiles and overcome drug resistance.

Main Methods:

  • Systematic design and synthesis of novel acridone compounds.
  • High-throughput screening for hypnozoitocidal activity against Plasmodium cynomolgi.
  • Evaluation of antimalarial activity in murine models of Plasmodium berghei infection.
  • Assessment of genotoxicity, cardiotoxicity, and cross-resistance profiles.

Main Results:

  • Numerous synthesized acridones demonstrated excellent antimalarial activity against both ABS and LS parasites.
  • Compounds showed favorable safety and metabolic profiles.
  • Several acridones inhibited schizont and hypnozoite formation in prophylactic and radical cure models.
  • Newer acridones mitigated cross-resistance with atovaquone.
  • Compound 28 (T229) achieved full LS protection and sustained blood-stage cure in mice, with low toxicity.
  • Compound 28 was effective against artemisinin-resistant parasites.

Conclusions:

  • A novel family of acridones possesses robust antirelapse activity against liver-stage malaria parasites.
  • These compounds represent a promising new class of antimalarials effective against drug-resistant strains and offering a radical cure.
  • Compound 28 is a potential candidate for further antimalarial drug development.