Kowalczyk-Bronisz S H, Pomorski J, Zabska R
Department of Experimental Therapy, Polish Academy of Sciences, Wrocław.
Arch Immunol Ther Exp (Warsz). 1988;36(3):249-67.
Several new aziridine derivatives of propionic acid were synthesized (10-15, 19, 20). o-, m-, p-Chloroanilide of chloroacetic acid 1-3 and chloride of 3-/p-chlorobenzoyl/acrylic acid 16 were the substrates. The compounds 1-3 in reaction with nicotine aldehyde or p-chlorobenzaldehyde were transformed into appropriate anilides of 2,3-epoxypropionic acid 4-9. These, in turn reacted with ethylenimine giving the appropriate 3-aziridine derivatives 10-15. Acid chloride 16 in reaction with amines gave the appropriate amides 17 and 18 which formed 2-aziridine derivatives 19 and 20 when under the influence of ethylenimine. Pharmacological analysis revealed that the aziridine derivatives 12-15, 19 and 20 modulate some immunological reactions with the prevailing effect of the suppressive component (PFC, RFC, IgM level, cellular response to SRBC). The stimulatory effect was observed with some compounds on the level of circulating IgG and GvH reaction. The mechanism of these compounds consists in their interference with the activity of Ts cells and mediators of the immunological reactions.
合成了几种新的丙酸氮丙啶衍生物（10 - 15、19、20）。氯乙酸的邻、间、对氯苯胺（1 - 3）和3 - /对氯苯甲酰基/丙烯酸氯（16）为底物。化合物1 - 3与烟碱醛或对氯苯甲醛反应转化为相应的2,3 - 环氧丙酸苯胺（4 - 9）。这些产物再与乙撑亚胺反应得到相应的3 - 氮丙啶衍生物（10 - 15）。酰氯16与胺反应得到相应的酰胺（17和18），在乙撑亚胺的影响下形成2 - 氮丙啶衍生物（19和20）。药理分析表明，氮丙啶衍生物12 - 15、19和20调节一些免疫反应，主要表现为抑制成分（PFC、RFC、IgM水平、对SRBC的细胞反应）的作用。一些化合物对循环IgG水平和移植物抗宿主反应有刺激作用。这些化合物的作用机制在于它们干扰Ts细胞的活性和免疫反应的介质。
