| 1. |
- Cerecetto, H, et al.
(författare)
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1,2,5-Oxadiazole N-oxide derivatives and related compounds as potential antitrypanosomal drugs : structure-activity relationships.
- 1999
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Ingår i: Journal of Medicinal Chemistry. - : American Chemical Society (ACS). - 0022-2623 .- 1520-4804. ; 42:11, s. 1941-50
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Tidskriftsartikel (refereegranskat)abstract
- The syntheses of a new series of derivatives of 1,2,5-oxadiazole N-oxide, benzo[1,2-c]1,2,5-oxadiazole N-oxide, and quinoxaline di-N-oxide are described. In vitro antitrypanosomal activity of these compounds was tested against epimastigote forms of Trypanosoma cruzi. For the most effective drugs, derivatives IIIe and IIIf, the 50% inhibitory dose (ID50) was determined as well as their cytotoxicity against mammalian fibroblasts. Electrochemical studies and ESR spectroscopy show that the highest activities observed are associated with the facile monoelectronation of the N-oxide moiety. Lipophilic-hydrophilic balance of the compounds could also play an important role in their effectiveness as antichagasic drugs.
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| 2. |
- Cerecetto, H, et al.
(författare)
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Synthesis and herbicidal activity of N-oxide derivatives
- 2000
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Ingår i: Journal of Agricultural and Food Chemistry. - : American Chemical Society (ACS). - 0021-8561 .- 1520-5118. ; 48:7, s. 2995-3002
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Tidskriftsartikel (refereegranskat)abstract
- As part of an ongoing program on the chemistry and biological activity of N-oxide-containing molecules, a number of novel 1,2,5-oxadiazole N-oxide, benzo[1,2-c]1,2,5-oxadiazole N-oxide, and quinoxaline N,N'-dioxide derivatives were synthesized and evaluated for their herbicidal activity. Many of these compounds exhibited moderate to good herbicidal pre-emergence activity against Triticum aestivum. Dose-response studies were done on the more representative compounds (12, 20, and 26). The most active compound, butylcarbamoylbenzo[1,2-c]l,2,5-oxadiazole N-oxide, 26, displayed herbicidal activity at concentrations as low as 24 g/ha.
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| 3. |
- Iribarne, F., et al.
(författare)
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Interaction energies of nitrofurans with trypanothione reductase and glutathione reductase studied by molecular docking
- 2007
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Ingår i: Journal of Molecular Structure. - : Elsevier BV. - 0166-1280. ; 818:1-3, s. 7-22
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Tidskriftsartikel (refereegranskat)abstract
- A theoretical docking study was conducted on a sample of previously reported nitrofuran derivatives, at the binding sites of Trypanosoma cruzi trypanothione reductase (TR) and human erythrocyte glutathione reductase (GR), in order to examine interaction energies (affinities) towards the parasite enzyme and check for selectivity with respect to the human counterpart. A large proportion of nitrofurans were previously shown to be TR inhibitors and some of them have in vitro trypanocidal action as well. The analysis of data collected from the docking procedure was undertaken both from the numeric and graphical standpoints, including the comparison of force field energies, molecular contacts and spatial location of the different orientations that ligands acquired at the binding sites. The results clearly suggest that nitrofurans are not able to selectively bind at the active site of the parasite TR, attaining even larger interaction energies at GR active site. The reason for inhibitor specificity is two-fold: (a) the nitrofuran group acts as a strong electrostatic anchor in GR; (b) the compounds form more stable complexes when binding at the non-selective dimmer interface. Therefore, these two aspects should be specially considered when seeking good candidates for leaders in regards the development of drugs with selective inhibition of TR.
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| 4. |
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