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| 一种新的合成salacinol衍生物的方法及其对α-糖苷酶的抑制活性 | |
| 引用本文： | 邵颖,村岡修,吉海和哉,松浦義治,山田惠理子,峯松敏江,田邉元三,松田久司,吉川雅之,尤启冬. 一种新的合成salacinol衍生物的方法及其对α-糖苷酶的抑制活性[J]. 药学学报, 2006, 41(7): 647-653 |
| 作者姓名： | 邵颖 村岡修 吉海和哉 松浦義治 山田惠理子 峯松敏江 田邉元三 松田久司 吉川雅之 尤启冬 |
| 作者单位： | 1. 中国药科大学,药物化学教研室,江苏,南京,210009 2. 日本近畿大学,药学院,大阪,577-8502 3. 日本京都药科大学,京都,607-8412 |
| 摘 要： | 目的探索更有效的合成salacinol及其衍生物的方法，以研发新的糖尿病治疗药。方法以d-葡萄糖为原料，经7步反应制得 salacinol及其衍生物合成的关键中间体 2,4-o-异丙亚基-l-赤藓糖醇-1,3-环硫酸酯(2a)；此方法成本明显低于文献报道的以l-葡萄糖为原料的合成方法。以此方法，制备salacinol的含氮衍生物4，并与salacinol进行了体外抑制α-葡糖苷酶活性的比较研究。结果采用此种新的路线，顺利制得salacinol的含氮衍生物(4)及结构简化物(13)。结论以d-葡萄糖为原料的新的合成路线优于文献方法，salacinol分子结构中的硫原子用氮原子替代时，其活性明显降低。 |
| 关 键 词： | 合成 环硫酸酯 赤藓糖醇 salacinol 糖苷酶抑制剂 葡糖苷酶抑制剂 氮杂糖 |
| 文章编号： | 0513-4870（2006）07-0647-07 |
| 收稿时间： | 2006-02-21 |
| 修稿时间： | 2006-02-21 |
Synthesis of a salacinol analogue and its α-glucosidase inhibitory activity |
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| SHAO Ying,OSAMU Muraoka,KAZUYA Yoshikai,YOSHIHARU Matsuura,ERIKO Yamada,TOSHIE Minematsu,GENZOH Tanabe,HISASHI Matsuda,MASAYUKI Yoshikawa,YOU Qi-dong. Synthesis of a salacinol analogue and its α-glucosidase inhibitory activity[J]. Acta pharmaceutica Sinica, 2006, 41(7): 647-653 | |
| Authors: | SHAO Ying OSAMU Muraoka KAZUYA Yoshikai YOSHIHARU Matsuura ERIKO Yamada TOSHIE Minematsu GENZOH Tanabe HISASHI Matsuda MASAYUKI Yoshikawa YOU Qi-dong |
| Affiliation: | Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China;School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan;School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan;School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan;School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan;School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan;School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan;Kyoto Pharmaceutical University, 1 Shichono-cho, Misasagi, Yamashinaku, Kyoto 607-8412, Japan;Kyoto Pharmaceutical University, 1 Shichono-cho, Misasagi, Yamashinaku, Kyoto 607-8412, Japan;Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China |
| Abstract: | AIM: To investigate more efficient synthetic method of the nitrogen analogue 4 of salacinol (1) for searching new antidiabetic agents. METHODS: 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. RESULTS: A nitrogen analogue 4 of salacinol (1) was synthesized by the coupling reaction between the cyclic sulfate 2a and an azasugar 3b. CONCLUSION: Substitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably. |
| Keywords: | salacinol synthesis cyclic sulfate erythritol salacinol glycosidase inhibitor glucosidase inhibitor azasugar |
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