Получены амиды 4-арил-2-[(2-оксо-1,2-дифенилэтилиден)гидразинил]-4-оксобут-2-еновых кислот дециклизацией 3-[(2-оксо-1,2-дифенилэтилиден)гидразоно]-5-арилфуран-2(3Н)-онов соответствующими аминами, а также взаимодействием гетариламидов 4-арил-2-гидрокси-4-оксобут-2-еновых кислот с 2-гидразоно-1,2-дифенилэтаноном. Изучена их анальгетическая и антибактериальная активность. Обнаружены вещества, сопоставимые и превышающие по активности препараты сравнения с низкой токсичностью.
4-Aryl-2-[(2-oxo-1,2-diphenylethylidene)hydrazinyl]-4-oxobut-2-enoic-acid amides were produced via decyclization of 3-[(2-oxo-1,2-diphenylethylidene)hydrazono]-5-arylfuran-2(3H)-ones by the corresponding amines and via reaction of 4-aryl-2-hydroxy-4-oxobut-2-enoic-acid hetarylamides with 2-hydrazono-1,2-diphenylethanone. Their analgesic and antibacterial activities were studied. Compounds with low toxicities and activities comparable to and exceeding those of reference drugs were discovered.
Hydrazones derived from substituted benzophenones and fluorenone reacted with 4-aryl-2-hydroxy-4-oxobut-2-enoic and 2-hydroxy-5,5-dimethyl-4-oxohex-2-enoic acids to give the corresponding 2-(2-ylidenehydrazino) derivatives which may be used as initial compounds for the synthesis of 3-hydrazono-3 H -furan-2-ones. The obtained but-2-enoic and hex-2-enoic acid derivatives in solution may exist as Z - and E -isomeric enehydrazine tautomers or hydrazone tautomers with syn or anti orientation of substituents with respect to the double C=N bond.
The title compounds (III) exist in solution as Z- and E-enehydrazino- or β-ketohydrazone forms.
Reactions of 1,2-diphenylethane-1,2-dione hydrazone with 4-aryl-2-hydroxy-4-oxobut-2-enoic and 2-hydroxy-5,5-dimethyl-4-oxohex-2-enoic acids provided 4-aryl-4-oxo-2-[2-(2-oxo-1,2-diphenylethylidene) hydrazino]but-2-enoic and 5,5-dimethyl-4-oxo-2-[2-(2-oxo-1,2-diphenylethylidene)hydrazino]hex-2-enoic acids. The acids derivatives can exist in solutions as Z - and β-enehydrazino-or β-ketohydrazone forms, and under the treatment with acetic anhydride they undergo cyclization into 5-aryl- and 5- tert -butyl-3-[2-(2-oxo-1,2-diphenylethylidene)hydrazono]-2,3-furandiones.