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Thiazide diuretics are sulfonamide derivatives featuring a benzothiadiazine ring system in their molecular structure. Based on this structure, thiazide diuretics can be categorized into two groups: thiazide-type and thiazide-like diuretics. Thiazide-type diuretics, including hydrochlorothiazide and chlorothiazide, consist of a benzothiadiazine backbone with an attached sulfonamide group. Thiazide-like diuretics, such as chlorthalidone and indapamide, lack the thiazide ring but demonstrate...
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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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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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ortho–para-Directing Deactivators: Halogens01:24

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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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Updated: Oct 25, 2025

Ookluc: A Plasmodium berghei Line for Identifying Transmission-blocking Compounds
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Polyhydroxybenzoic acid derivatives as potential new antimalarial agents.

Gilles Degotte1,2, Bernard Pirotte1, Michel Frédérich2

  • 1Department of Pharmacy, Laboratory of Medicinal Chemistry, CIRM, University of Liège, Liège, Belgium.

Archiv Der Pharmazie
|August 4, 2021
PubMed
Summary

Malaria drug resistance necessitates new treatments. Gallic acid derivatives show promise, with one compound demonstrating significant anti-malarial activity and good water solubility for future drug development.

Keywords:
Plasmodiumgallic acidhydroxybenzoic acidmalariamedicinal chemistry

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Area of Science:

  • Medicinal Chemistry
  • Parasitology
  • Drug Discovery

Background:

  • Malaria remains a major global health threat, with over 200 million cases and 400,000 deaths in 2021.
  • Increasing drug resistance in Plasmodium parasites is driving a rise in malaria cases, highlighting the urgent need for novel antimalarial agents.

Purpose of the Study:

  • To explore polyhydroxybenzoic acids as potential antimalarial scaffolds.
  • To synthesize and evaluate a library of derivatives for antiplasmodial activity and structure-activity relationships.

Main Methods:

  • Synthesis of polyhydroxybenzoic acid derivatives.
  • Evaluation of antiplasmodial activity against Plasmodium parasites.
  • Assessment of selectivity and water solubility.

Main Results:

  • Gallic acid derivatives exhibited significant selective antiplasmodial activity (IC50 ~20 µM, SI > 5).
  • The presence of free phenolic functions (pyrogallol moiety) is crucial for antimalarial efficacy.
  • Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) demonstrated potent activity and good hydrosolubility (3.72 mM), identifying it as a promising lead compound.

Conclusions:

  • Gallic acid derivatives represent a viable starting point for developing new antimalarial drugs.
  • The pyrogallol moiety is essential for the antiplasmodial effect of these compounds.
  • Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) is a promising candidate for further antimalarial drug development.