S-, N-, and O-glycosyl derivatives of 2-acetamido-2-deoxy-d-glucose with hydrophobic aglycons as potential chemotherapeutic agents and N-acetyl-β-d-glucosaminidase inhibitors
作者:Brajeswar Paul、Walter Korytnyk
DOI:10.1016/0008-6215(84)85124-1
日期:1984.3
S-, N-, and O-Glycosyl derivatives of 2-acetamido-2-deoxy-D-glucose with hydrophobic aglycons have been obtained as potential, plasma-membrane active agents. 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-beta-D-glucopyranose (6) was converted into benzyl, diphenylmethyl, triphenylmethyl, and other thioglycosides. Acylation of 6 gave adamantoyl and haloacetyl derivatives. A similar series of N- and
已经获得了2-乙酰氨基-2-脱氧-D-葡萄糖与疏水性糖苷配基的S-,N-和O-糖基衍生物作为潜在的血浆膜活性剂。将2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-1-硫代-β-D-吡喃葡萄糖(6)转化为苄基,二苯甲基,三苯甲基和其他硫代糖苷。酰化6得到金刚烷基和卤代乙酰基衍生物。从相应的6的NH2-1和OH-1类似物获得了一系列类似的N-和O-糖基衍生物,例如O-和N-二硝基苯基,O-和N-金刚烷基以及N-4-甲基亚苄基衍生物。发现几种N-和S-糖基衍生物可在体外抑制小鼠的乳腺腺癌(TA3)细胞以及牛肉肝中的N-乙酰基-β-D-氨基葡萄糖苷酶。