RESUMEN
A series of novel pyridine and fused pyridine derivatives have been prepared starting from 6-(3,4-dimethylphenyl)-2-hydrazinyl-4-(thiophen-2-yl)-pyridine-3-carbonitrile 1 which on treatment with appropriate formic acid, acetic acid/ acetic anhydride, benzoyl chloride and/or carbon disulfide afforded the corresponding triazolopyridine derivatives 2â»5. Also, treatment of hydrazide 1 with diethyloxalate, chloroacetyl chloride, chloroacetic acid and/or 1,2-dichloroethane yielded the corresponding pyridotriazine derivatives 7â»10. Further transformation of compound 1 with a different active methylene group, namely acetyl acetone, diethylmalonate, ethyl cyanoacetate, ethyl benzoylacetate and/or ethyl acetoacetate, produced the pyridineâ»pyrazole hybrid derivatives 11â»15. These newly synthesized compounds (1â»15) were subjected to in silico molecular docking screenings towards GlcN-6-P synthase as the target protein. The results revealed moderate to good binding energies of the ligands on the target protein. All the newly prepared products exhibited antimicrobial and antioxidant activity.
Asunto(s)
Antibacterianos/síntesis química , Antiinfecciosos/síntesis química , Pirazoles/síntesis química , Piridinas/química , Ácido Acético/síntesis química , Ácido Acético/química , Antibacterianos/química , Antibacterianos/farmacología , Antiinfecciosos/química , Antiinfecciosos/farmacología , Benzoatos/química , Disulfuro de Carbono/síntesis química , Disulfuro de Carbono/química , Formiatos/síntesis química , Formiatos/química , Glucosamina/análogos & derivados , Glucosamina/química , Glucosa-6-Fosfato/análogos & derivados , Glucosa-6-Fosfato/química , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , Pirazoles/química , Pirazoles/farmacología , Piridinas/síntesis química , Piridinas/farmacología , Relación Estructura-ActividadRESUMEN
This contribution studies the decomposition of folpet fungicide under oxidative conditions and compares the product species with those of captan fungicide, which is structurally related to folpet. Toxic products arising from folpet comprised carbon disulfide (highest emission factor of 4.9 mg g(-1) folpet), thiophosgene (14.4), phosgene (34.1), hydrogen cyanide (2.6), tetrachloroethylene (111), hexachloroethane (167), and benzonitrile (4.5). Owing to their related molecular structures, folpet emitted similar products to captan but at different yields, under the same experimental conditions. It appears that the availability of easily abstractable H atoms, in the structure of captan but not in that of folpet, defines the product distribution. In conjunction with the quantum chemical calculations, these experimental measurements afford an enhanced explanation of the formation pathways of hazardous decomposition products of these two structurally related fungicides.
Asunto(s)
Contaminantes Atmosféricos/síntesis química , Fungicidas Industriales/química , Calefacción/métodos , Ftalimidas/química , Compuestos Orgánicos Volátiles/síntesis química , Contaminantes Atmosféricos/análisis , Captano/química , Disulfuro de Carbono/análisis , Disulfuro de Carbono/síntesis química , Etano/análogos & derivados , Etano/análisis , Etano/síntesis química , Hidrocarburos Clorados/análisis , Hidrocarburos Clorados/síntesis química , Incineración , Estructura Molecular , Nitrilos/análisis , Nitrilos/síntesis química , Oxidación-Reducción , Tetracloroetileno/análisis , Tetracloroetileno/síntesis química , Compuestos Orgánicos Volátiles/análisisRESUMEN
An efficient method for the synthesis of symmetrical and unsymmetrical substituted thiourea derivatives by means of simple condensation between available building blocks such as amines and carbon disulfide in aqueous medium is presented. This protocol works smoothly with aliphatic primary amines to afford various di- and trisubstituted thiourea derivatives. The present method is also useful in synthesizing various substituted 2-mercapto imidazole heterocycles. This method proceeds through a xanthate (amino dithiol deivative) intermediate, unlike isothiocyanate as in an earlier known method.
Asunto(s)
Aminas/química , Disulfuro de Carbono/síntesis química , Compuestos Heterocíclicos/síntesis química , Compuestos de Sulfhidrilo/síntesis química , Tiourea/síntesis química , Agua/química , Disulfuro de Carbono/química , Técnicas Químicas Combinatorias , Cristalografía por Rayos X , Compuestos Heterocíclicos/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Estereoisomerismo , Relación Estructura-Actividad , Compuestos de Sulfhidrilo/química , Tiourea/químicaRESUMEN
Condensations of carbon disulfide were carried out with amino, chloro, and diamino heterocycles to give condensed ring thiazoline-2-thiones and imidazoline-2-thiones, with cyanomethyl heterocycles to give dithio acid derivatives, and with heterocyclic sulfonamides to give sulfonyldithiocarbamates. Of several examples tested, pyrido[3,2-d]thiazoline-2-thione, disodium 2-(5-chloro-2-thienyl)-3,3-dimercaptoacrylonitrile, triethylammonium 4-sulfamoylphenyldithiocarbamate, ammonium beta-phenethyldithiocarbamate, and methyl N-(thiophene-2-sulfonyl)dithiocarbamate, only the last-named compound showed any radiation protection for mice. Several compounds gave negative tests for antimalarial activity.
Asunto(s)
Acetonitrilos/síntesis química , Aminas/síntesis química , Disulfuro de Carbono/síntesis química , Cloro , Compuestos Heterocíclicos/síntesis química , Protectores contra Radiación/síntesis química , Sulfonamidas/síntesis química , Animales , Antimaláricos/síntesis química , Antimaláricos/farmacología , Fenómenos Químicos , Química , Ratones , Protectores contra Radiación/farmacologíaRESUMEN
In order to understand the role of sulfur in the primitive atmosphere, we have studied the action of a silent discharge on mixtures of CH4 and H2S at low pressure. The nature of the products formed in the gaseous phase, and the influence of several parameters, especially the H2S percentage, on the yield of the products are reported. The analysis of the products is carried out by gas liquid chromatography and infrared spectrometry. The formation of sulfur-containing compounds, such as thiols and sulfides, is reported. CS2 is formed in high yield (a few percent) in mixtures containing 40-50% of H2S, while the maximum concentration of thiols (i.e., CH3SH and C2H5SH) is reached with lower percentages of H2S. The formation of hydrocarbons decreases rapidly with increasing proportions of H2S. These results show the important inhibitor effect of H2S on the formation of hydrocarbons and the possibility of occurrence of many sulfur compounds in prebiological evolution.