Synthesis and antileukaemia activity of N-(2,4-dimethylphenyl)hydrazine carbothioamide and its azomethine derivatives [Articol]

Abstract

Prezenta lucrare conţine date despre sinteza, caracterizarea şi evaluarea in vitro a activităţii biologice a N-(2,4-dimetilfenil)hidrazinocarbotioamidei şi a cinci derivaţi azometinici ai acesteia, obţinuţi prin condensarea N-(2,4-dimetilfenil)hidrazincarbotioamidei cu diferiţi compuşi carbonilici. Compoziţia şi structura cristalină a compuşilor sintetizaţi a fost determinată cu ajutorul spectroscopiei 1H, 13C RMN şi a difracţiei cu raze X a monocristalelor. Toţi compuşii obţinuţi au fost testaţi ca inhibitori ai proliferării celulelor de leucemie umană HL-60. A fost stabilit că N-(2,4-dimetilfenil)-2-(tiofen- 3-ilmetilen)hidrazinocarbotioamida şi N-(2,4-dimetilfenil)-2-(2-hidroxibenziliden) hidrazinocarbotioamida sunt cei mai activi agenţi antiproliferativi obţinuţi în acest studiu.Настоящая работа описывает данные о синтезе, характеристике и определении биологической активности in vitro N-(2,4-диметилфенил)гидразинкарботиоамида и пяти его азометиновых производных, полученных путем конденсации N-(2,4-диметилфенил) гидразинкарботиоамида с различными карбонильными соединениями. Химический состав и структура синтезированных веществ были установлены с помощью 1H, 13C ЯМР спектроскопии и рентгеноструктурного анализа. Все вещества были протестированы на противолейкемическую (HL-60) активность. Было установлено, что наиболее активными являются N-(2,4-диметилфенил)-2-(тиофен-3-илметилен)гидразинкарботиоамид и N-(2,4- диметилфенил)-2-(2-гидроксибензилиден)гидразинкарботиоамид.The present paper concerns data on the synthesis, characterisation and in vitro biological activity evaluation of N-(2,4-dimethylphenyl)hydrazinecarbothioamide and its fi ve azomethine derivatives, obtained by condensation of N-(2,4-dimethylphenyl)hydrazinecarbothioamide with different carbonilic compounds. The composition and the crystal structure of the synthesised compounds have been defi ned by means of 1H, 13C NMR spectroscopy and X-ray diffraction. All compounds produced have been tested as inhibitors of human leukaemia (HL-60) cells growth. N-(2,4-dimethylphenyl)-2-(thiophene-3-ylmethylene) hydrazinecarbothioamide and N-(2,4-dimethylphenyl)-2-(2-hydroxybenzylidene) hydrazinecarbothioamide have been found to be the most antiproliferative active agents among those obtained in this study.