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New Phosphoramidates Containing Selenium as Leishmanicidal Agents.

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Summary

This study synthesized novel selenophosphoramidate derivatives for leishmaniasis treatment. Compound 1g demonstrated significant leishmanicidal activity and favorable drug-like properties, suggesting potential for new anti-leishmania therapies.

Keywords:
diselenidephosphoramidateselenocyanatethiolstrypanothione reductase

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Area of Science:

  • Medicinal Chemistry
  • Parasitology
  • Organic Synthesis

Background:

  • Leishmaniasis remains a significant global health concern requiring new therapeutic strategies.
  • Existing treatments face challenges including toxicity and drug resistance.
  • Novel chemical scaffolds are needed to develop effective leishmanicidal agents.

Purpose of the Study:

  • To synthesize and characterize new selenophosphoramidate derivatives.
  • To evaluate the in vitro leishmanicidal activity of these novel compounds.
  • To investigate the mechanism of action and drug-like properties of promising candidates.

Main Methods:

  • Synthesis of 13 new selenophosphoramidate derivatives.
  • Characterization using FTIR, NMR (¹H, ¹³C, ⁷⁹Se), mass spectrometry, and elemental analysis.
  • In vitro evaluation of leishmanicidal activity against infected macrophages.
  • Assessment of trypanothione redox system alteration.
  • Theoretical calculations for physicochemical and pharmacokinetic properties.

Main Results:

  • Successful synthesis and full characterization of 13 novel selenophosphoramidate derivatives.
  • Identification of four compounds (1f, 1g, 2f, 2g) with potent leishmanicidal activity.
  • Compound 1g showed superior efficacy compared to reference drugs and altered the trypanothione redox system.
  • Compound 1g exhibited favorable physicochemical and pharmacokinetic properties for oral bioavailability.

Conclusions:

  • Selenophosphoramidate derivatives represent a promising scaffold for developing new leishmanicidal agents.
  • Compound 1g is a lead candidate for further development in leishmaniasis treatment.
  • The observed mechanism involves the trypanothione redox system, offering insights for drug design.