The crystal structures of (Z)-1-phenyl-4-[((2-phenylhydrazono)methyl)]-1H-1,2,3-triazole, (Z)-4-[(2-(2,4-dimethylphenyl)hydrazono)methyl]-2-phenyl-2H-1,2,3-triazole, (E)-4-[(2-(2,4-dinitrophenyl)hydrazono)methyl]-2-phenyl-2H-1,2,3-triazole, and (E)-N'-((2-phenyl-2H-1,2,3-triazol-4-yl)methylene)isonicotinohydrazide dihydrate are reported. The formations of (Z)- configurations about the C=N bonds in the first two compounds arise from the stabilizing presence of intramolecular N-H···N hydrogen bonds, while in the third compound, the presence of intramolecular N-H···O hydrogen bonds promotes an (E) geometry. The arrangement about the CONHC=N fragment in the hydrated acylhydrazone is EC(O)NH/EC=N. Also present in (E)-N'-((2-phenyl-2H-1,2,3-triazol-4-yl)methylene)isonicotinohydrazide is an interesting R44(8) ring formed from hydrogen bonds generated from four water molecules. Significant π···π stacking interactions are exhibited in three compounds, but not in the least planar first compound, in which the dominant intermolecular interactions are C-H···π interactions. Other intermolecular interactions in one of the compounds are C-H···π interactions, in another compound are C-H···O hydrogen bonds and N-O···π interactions, and in the last compound are O-H···X (X = O and N), N-H···O and C-H···O hydrogen bonds.

Este artigo descreve a síntese e a atividade antileishmania de novos derivados pirazolil benzenossulfonamídicos. Estes foram elucidados por métodos espectrométricos. Alguns compostos mostraram uma atividade in vitro significativa contra Leishmania amazonensis, destacando-se o derivado 1e. Nenhum dos derivados pirazolil benzenossulfonamídicos mostraram qualquer toxicidade em macrófagos murinos.

This paper describes the synthesis and the antileishmanial activity of new pyrazolyl benzenesulfonamide derivatives. These were elucidated by spectrometric methods. Some compounds showed a significant in vitro activity against Leishmania amazonensis, highlighting the derivative 1e. These pyrazolyl benzenesulfonamide derivatives did not show any toxicity in murine macrophage.

Este trabalho descreve a versatilidade sintética dos derivados N-Acil-3,3-diflúor-2-oxoindóis, obtidos a partir da reação de N-acilisatinas com dietilaminotrifluoreto de enxofre (DAST) que, através da reação com diferentes nucleófilos, promovem a abertura do anel heterocíclico, levando à formação de vários produtos. A reação de N-Acil-3,3-diflúor-2-oxoindóis com água fornece os ácidos 2-(2-N-acilfenil)-2,2-difluoracéticos e com álcoóis fornece os ésteres correspondentes. Reações com aminas e glicina levam à formação das correspondentes amidas 2-(2-N-acilfenil)-2,2-difluoracetamidas. Na reação com tiossemicarbazidas os derivados difluortiossemicarbazidas são obtidos. Estes últimos sofrem uma ciclização catalisada por ácido para fornecer N-(2-((5-aminoaril-1,3,4-tiadiazol-2-il)difluormetil)-4-(R)-fenil)acetamida. A estrutura de N-(2-((5-amino-1,3,4-tiadiazol-2-il)difluormetil)-4-metilfenil)acetamida foi determinada por raio-X.

This paper describes the versatility of N-Acyl-3,3-difluoro-2-oxoindoles, obtained from the the reaction of N-acylisatins with (diethylamino)sulphur trifluoride (DAST) which, on opening of the heterocyclic ring by reactions with nucleophiles, lead to the formation of a variety of products: reaction with water yields 2-(2-amidoacyl)-2,2-difluoroacetic acids, with alcohols yields alkyl 2-(2-amidoacyl)-2,2-difluoroacetates, with amines and glycine yields 2-(2-amidoacyl)-2,2-difluoroacetamides and with thiosemicarbazides yields difluorothiosemicarbazide derivatives. The latter undergo acid-catalysed cyclizations to yield N-(2-((5-aminoaryl-1,3,4-thiadiazol-2-yl)difluoromethyl)-4-(R)-phenyl)acetamide. The X-ray structure of N-(2-((5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl)-4-methylphenyl)acetamide has been determined.

Um método mais suave e eficiente é descrito para a síntese de 3-(2'-aminoaril)pirazóis, a partir das reações de 4-cloroquinolinas com hidrazina em excelentes rendimentos. Estas reações de abertura de anel heterocíclico ocorrem em condições mais suaves do que as descritas anteriormente.

We describe a mild and efficient method for the formation of 3-(2'-aminoaryl)pyrazoles in excellent yields from reactions of 4-chloroquinolines with hydrazine. These heterocyclic ring opening reactions occur under much milder conditions then previously described.