R Caujolle

Aromatic ethers of 1-aryl 2-(1H-azolyl)ethanol: study of antifungal activity

Summary Aromatic ethers related to antifungal azole miconazole were synthesized and tested against various strains of Candida. We found that activity is related to the nature of the aromatic ring and the position of substituents on this ring. Activity is more strongly dependent on the substituent in the 2 position of the ethyl chain than on the aromatic group linked through the oxygen. Triazoles were always less potent than the corresponding imidazole analogues.

Aminothiazines et aminothiazoles analogues ouverts du lévamisole: synthèse et approche du mode d'action nématicide

New compounds with thiazoline or dihydrothiazine rings substituted by alkylamino or arylamino groups were synthesized and screened in vitro against three Nematodes. Inhibition of fumarate-reductase activity was also evaluated. For all in vitro anti-parasitic tests, dihydrothiazines were more potent than corresponding thiazolines derivatives, however, thiazolines showed a greater inhibition of fumarate-reductase.

Synthèse, activités anti-parasitaire et anti-fongique d'arylalkyl- et d'arylvinylthiazolines

Abstract Twenty-seven arylalkyl- or arylvinylthiazolines were synthesized and tested in vitro against three genera of nematodes, various yeasts and opportunistic fungi. Vinyl compounds seem to have an interesting filaricidal activity against Molinema dessetae and anti-fungal activity against yeasts.

Aliphatic ethers and esters of 1-(2,4-dichlorophenyl)-2-(1H-imidazolyl) ethanol : study of antifungal activity against yeasts and hydrophobic character

Aliphatic ethers 2 and esters 3, which are closely related to antifungal azoles, were synthesized and tested against various strains of Candida. We found that their activity was strongly related to the length of the chains; the best activity was obtained with a C-6 chain for ethers and C-5 or C-6 chains for esters (including the carbonyl group), whereas shorter or longer alkyl chains decreased antifungal efficiency. The biological activity of such compounds could be related to their ability to bind with the lipophilic area near the active site of enzymatic target. The lipophilic character increases with the length of chain, following a linear variation. Thus, even if the activity depends on the lipophilic influence, this particular property is not sufficient to totally explain the antifungal efficiency.

Synthesis and nematocidal activities of new analogs of pyrantel

Summary A set of new analogs of pyrantel was synthesized in good yields by lithiation of 1,2-dimethyltetrahydropyrimidine with n -butyllithium in tetrahydrofuran and condensation with aromatic esters. Spectrometric studies showed the large influence of intramolecular bonding in the tautomeric equilibria between the possible structures. Anthelmintic screening showed in vitro efficiency against Molinema dessetae , but a weak activity against Rhabditis pseudoelongata and Nippostrongylus brasiliensis .

Synthesis and biological evaluation of ureido and thioureido derivatives of 2-amino-2-deoxy-d-glucose and related aminoalcohols as N-acetyl-β-d-hexosaminidase inhibitors

Ureido and thioureido derivatives of 2-acetamido-2-deoxy-beta-D-glucose, 1-amino-1-deoxy-D-glucitol and 2-(2-aminoethoxy)ethanol were prepared as N-acetyl-beta-D-hexosaminidase (NAHase) inhibitors and were evaluated on Trichomonas vaginalis NAHase. Although none showed complete inhibition of the enzyme at 100 microM, 1-amino-1-deoxy-D-glucitol derivatives acted as competitive inhibitors of the NAHase of T. vaginalis.

Synthesis, antifungal and nematocidal activities of thioureines with an aminoester sequence

Twenty-three arylthioureines bearing β-alanine or γ-aminobutyric alkyl ester chains were synthesized for in vitro screening toward 44 strains of fungi and 2 genera of nematodes. The nitro derivatives were the most potent compounds against Aspergillus and Candida strains. Ester chains increase activity against the filarial worm Molinema dessetae. Twelve compounds have EC 50 < 40 μg/ml. However, the anthelmintic potency is weak compared with tetramisole

Aliphatic ethers of 1-(2,4-dichlorophenyl)-2-(1-H-imidazolyl)ethanol: influence of ramification and/or unsaturation on lipophilicity and antifungal activity

Summary Ethers of 1-(2,4-dichlorophenyl)-2-(1- H -imidazolyl)ethanol bearing ramified and/or unsaturated chains have been synthesized in order to specify the role of lipophilicity or steric contributions on antifungal activity against yeast for miconazole-like structures. The presence of ramifications on aliphatic chains (between 4 and 7 carbons) or unsaturation at the end, increases antifungal activity. For these compounds, lipophilicity seems to be counterbalanced by steric contributions.