Biomedical subjects
Publications and source records attributed to J Elguero.
The synthesis and the antiparasitic evaluation of twelve new 5-nitroimidaole derivatives has been carried out. The most effective compounds were the less hydrophilic pyridinium and imidazolium salts (IV), (V) and (X), and above all the tetrahydropyridine derivatives (XII) and (XIII).
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The mean hydrophobic contributions, pi*m, of substituents in a sample of 34 monosubstituted pyridines has been determined by using reversed-phase high-performance liquid chromatography. The values are compared with those obtained for benzene.
C10H14O5, Mr = 214.22, orthorhombic, P2(1)2(1)2(1), a = 14.1084 (6), b = 10.6443 (3), c = 7.1970 (1) A, V = 1080.80 (6) A3, Z = 4, D chi = 1.317 Mg m-3, Cu K alpha, lambda = 1.5418 A, mu = 0.8571 mm-1, F(000) = 456, T = 293 K, R = 0.052 for 816 observed [3 sigma (I)] Friedel pairs. The determined absolute configuration may be described as 3S, 4R, 5R, the five-membered ring having an envelope conformation, with the bulky substituents at cis positions. The bond lengths and angles are in agreement with those of the bromoacetoxy derivative.
Several heterocyclic analogues of triphenylmethane dyes have been synthesized. Their in vitro activity has been evaluated using the epimastigote forms of Trypanosoma cruzi as an assay system. The malachite green and gentian violet dyes previously reported as trypanocidal agents were also tested for comparison. Among the compounds tested, the 2-benzothienyl-bis-(4,4'-dimethylaminophenyl) derivative proved to be the most interesting, because of its high selectivity in killing parasites. The ID50, defined as the concentration which produced 50% reduction in (3H) thymidine incorporation in DNA after 18 hours or in viable parasites after five days of incubation with the above compounds, was 0.2 ng ml-1 and less than 1 ng ml-1, respectively. The relative toxicity, measured by its effect on cultured human HeLa cells, was over 10,000-fold higher. By contrast, gentian violet only showed a ten-fold higher inhibitory effect for T. cruzi. The other derivatives synthesized were active in various degrees. According to these results, a structure-activity relationship for these compounds is proposed.
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Explore the source record for details and available documents.
Explore the source record for details and available documents.
5H-Mebendazole and some related heterocyclic methyl carbamates were synthesized and their anthelmintic activity against Caenorhabditis elegans was determined. In order to study the influence of the heteroaromatic region with regard to the carbamate moiety on biological activity, the molecular electrostatic potentials (MEP) of all structures were calculated and a structure-activity relationship (SAR) was established. The electrostatic pattern of activity includes two minima of the carbamate moiety, a third heterocyclic minimum, and a pi-electronic region.