Shao Ying, Osamu Muraoka, Kazuya Yoshikai, Yoshiharu Matsuura, Eriko Yamada, Toshie Minematsu, Genzoh Tanabe, Hisashi Matsuda, Masayuki Yoshikawa, You Qi-dong
Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
Yao Xue Xue Bao. 2006 Jul;41(7):647-53.
To investigate more efficient synthetic method of the nitrogen analogue 4 of salacinol (1) for searching new antidiabetic agents.
The synthesis of the key intermediate 2, 4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate (2a) was accomplished by modification of reports from D-glucose via seven steps in much more less expensive. Using this method, an efficient synthesis of 4 was carried out. The glycosidase inhibitory activity of 4 was tested for the intestinal alpha-glucosidase in vitro and compared with that of salacinol.
A nitrogen analogue 4 of salacinol (1) was synthesized by the coupling reaction between the cyclic sulfate 2a and an azasugar 3b.
Substitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably.
研究更高效的萨拉辛醇（1）的氮类似物4的合成方法，以寻找新型抗糖尿病药物。
通过对D-葡萄糖相关报道进行改进，经七步反应以更低成本完成关键中间体2,4-O-异丙叉基-L-赤藓糖醇1,3-环硫酸酯（2a）的合成。采用该方法，实现了4的高效合成。对4进行体外肠道α-葡萄糖苷酶抑制活性测试，并与萨拉辛醇进行比较。
通过环硫酸酯2a与氮杂糖3b之间的偶联反应合成了萨拉辛醇（1）的氮类似物4。
将1中的硫原子替换为氮原子会显著降低活性。
