Muraoka Osamu, Yoshikai Kazuya, Takahashi Hideo, Minematsu Toshie, Lu Guangxin, Tanabe Genzoh, Wang Tao, Matsuda Hisashi, Yoshikawa Masayuki
School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
Bioorg Med Chem. 2006 Jan 15;14(2):500-9. doi: 10.1016/j.bmc.2005.08.040. Epub 2005 Sep 29.
Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring alpha-glucosidase inhibitor, salacinol (1a), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their alpha-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to 1a, and proved the importance of cooperative role of the polar substituents for the alpha-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described.
通过硫代糖1,4 - 二脱氧 - 1,4 - 环硫代 - D - 阿拉伯糖醇（3）与环硫酸盐（8、9和10）的偶联反应，合成了天然存在的α - 葡萄糖苷酶抑制剂萨拉辛醇（1a）侧链中缺乏极性取代基的三种类似物（5、6和7），并检测了它们的α - 葡萄糖苷酶抑制活性。与1a相比，所有这些更简单的类似物（5、6和7）的抑制活性均较低，这证明了极性取代基对α - 葡萄糖苷酶抑制活性的协同作用的重要性。还描述了一种从D - 木糖出发合成3的实用合成路线。
