Murakami M, Ikeda K, Achiwa K
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
Carbohydr Res. 1996 Jan 4;280(1):101-10. doi: 10.1016/0008-6215(95)00295-2.
The 9-amino or 9-N-acyl-5-trifluoroacetyl methyl alpha-ketosides (1a-c) and their 2,3-didehydro analogs (2a-c) have been synthesized through Neu5Ac aldolase-catalyzed aldol reaction of 6-azido-2-benzyloxycarbonylamino-2-deoxy-D-mannose with sodium pyruvate. The six compounds were investigated as inhibitors of sialidase from influenza virus. Compound 2b, a 2,3-didehydro type, showed the most potent inhibitory activity (IC50 > 7.8 microM) against the enzyme, whereas, compounds 1a-c as the methyl alpha-glycosides were found to be practically inactive (IC50 > 100 microM).
通过Neu5Ac醛缩酶催化6-叠氮基-2-苄氧羰基氨基-2-脱氧-D-甘露糖与丙酮酸钠的醛醇缩合反应，合成了9-氨基或9-N-酰基-5-三氟乙酰基甲基α-酮糖苷（1a - c）及其2,3-二脱氢类似物（2a - c）。研究了这六种化合物作为流感病毒唾液酸酶抑制剂的活性。2,3-二脱氢型化合物2b对该酶表现出最强的抑制活性（IC50 > 7.8 μM），而作为甲基α-糖苷的化合物1a - c实际上没有活性（IC50 > 100 μM）。
