Zawisza T, Matczak H, Kowalczyk-Bronisz S H, Jakóbiec T
Arch Immunol Ther Exp (Warsz). 1981;29(2):235-48.
Three groups of compounds:1,3-thiazine derivatives, 2-thiobarbituric acid derivatives and noncyclic thioureide were obtained as a result of condensation of some N, N1-derivatives of thiocarbamide and malonyl dichlorides, depending on the reaction conditions and chemical character of reagents. It was observed that the substituents beside nitrogen atoms of thiocarbamides, the kind of acid chloride and reaction conditions influenced the course of reaction. The structure of the newly synthesized compounds was proved by the analysis of PMR spectrum and the interpretation of IR spectrum. In the performed pharmacological examination immunotropic and anti-inflammatory activity of these compounds was determined. Among 1,3-thiazine derivatives, 5,5-diallyl-2-phenylimino-3-phenyl-2,3,4,5-tetrahydro-[1,3]-thiazine-4,6-dione and 5,5-diethyl-2-phenylimino-3-naphtyl-2,3,4,5-tetrahydro-[1,3]-thiazine-4,6-dione exhibited anti-inflammatory activity. The compounds also contained the immunotropic component, either stimulatory or suppressive, 2-thiobarbituric acid derivatives displayed stronger anti-inflammatory activity correlated mostly with the immunosuppressive activity. Some interdependence between chemical structure and biological activity in the group of the investigated 1,3-thiazines and 2-thiobarbituric acid derivatives was observed.
根据反应条件和试剂的化学性质，通过硫脲的一些N,N'-衍生物与丙二酰二氯缩合，得到了三组化合物：1,3-噻嗪衍生物、2-硫代巴比妥酸衍生物和非环状硫脲。观察到硫脲氮原子旁的取代基、酰氯的种类和反应条件会影响反应进程。通过对核磁共振氢谱（PMR）的分析和红外光谱（IR）的解析证实了新合成化合物的结构。在进行的药理实验中，测定了这些化合物的免疫调节和抗炎活性。在1,3-噻嗪衍生物中，5,5-二烯丙基-2-苯基亚氨基-3-苯基-2,3,4,5-四氢-[1,3]-噻嗪-4,6-二酮和5,5-二乙基-2-苯基亚氨基-3-萘基-2,3,4,5-四氢-[1,3]-噻嗪-4,6-二酮表现出抗炎活性。这些化合物还含有免疫调节成分，既有刺激作用也有抑制作用，2-硫代巴比妥酸衍生物表现出较强的抗炎活性，且大多与免疫抑制活性相关。在所研究的1,3-噻嗪和2-硫代巴比妥酸衍生物组中，观察到化学结构与生物活性之间存在一定的相互关系。
