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在三乙胺的作用下,以α-氯代-1’,2’-二-O-环亚己基二氧乙基甲醛肟产生的氧化腈为偶极体,N-芳基-马来酰亚胺为亲偶极体,通过1,3-偶极环加成反应合成了15个3-(1’,2’-二-O-环亚己基二氧乙基)-5-芳基-3a,6a-二氢-4,6-二氧代氮杂茂并[3’,4’-d]异噁唑啉衍生物(3a～3o),利用1H NMR、IR和元素分析对其结构进行了表征,并进行了初步活性筛选,部分化合物显示了不同程度的抗癌、抗炎及免疫性疾病活性。初步体外抗癌活性结果表明,当样品浓度为20μg.mL 1时,化合物3e、3h、3j和3l对Cdc25A磷酸酯酶的抑制率分别为60.6%、58.6%、51.4%和98.4%,其中3l的抑制率最高,甚至当样品浓度为5μg.mL 1时,化合物3l的抑制率仍为86.97%,值得进一步研究。此外,初步体外白细胞共同抗原活性结果表明,当样品浓度为20μmol.mL 1时,化合物3e、3l和3n对CD45蛋白酪氨酸磷酸酶A的抑制率分别为57.7%、74.4%和77.3%。在此基础上,初步讨论了该类化合物的构效关系。
The nitrile oxide produced with α-chloro-1 ’, 2’-di-O-cyclohexylidenedioxy ethylformaldehyde oxime under the action of triethylamine is a dipole, N-aryl-maleoyl The imine is a dipole-dipole ligand and 15 3- (1 ’, 2’-di-O-cyclohexylidenedioxyethyl) -5-aryl- 3a, 6a-dihydro-4,6-dioxoamino [3 ’, 4’-d] isoxazoline derivatives (3a ~ 3o) Were characterized, and the initial screening activity, some of the compounds showed varying degrees of anti-cancer, anti-inflammatory and immune disease activity. The preliminary anticancer activity in vitro showed that the inhibitory rates of 3e, 3h, 3j and 3l on Cdc25A phosphatase were 60.6%, 58.6%, 51.4% and 98.4% respectively when the concentration was 20μg.mL 1, of which 3l The highest inhibitory rate, even when the sample concentration of 5μg.mL 1, the inhibition rate of compound 3l still 86.97%, worth further study. In addition, preliminary leukocyte antigen activity in vitro showed that the inhibitory rates of 3e, 3l and 3n on CD45 protein tyrosine phosphatase A were 57.7%, 74.4% and 77.3%, respectively, when the sample concentration was 20μmol.mL 1. On this basis, the structure-activity relationship of these compounds is discussed preliminarily.