1,4-dideoxy-1,4-[(R)-[4-deoxy-2-O-(1-tridecyl)-D-erythritol-4-yl]episulfoniumylidene]-D-arabitol chloride | 1392478-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: 1,4-dideoxy-1,4-[(R)-[4-deoxy-2-O-(1-tridecyl)-D-erythritol-4-yl]episulfoniumylidene]-D-arabitol chloride
• 英文别名: 1,4-dideoxy-1,4-{(R)-[4-deoxy-3-O-(tridec-1-yl)-D-erythritol-4-yl]episulfoniumylidene}-D-arabinitol chloride
• CAS: 1392478-94-2
• 化学式: C₂₂H₄₅O₆S*Cl
• 分子量: 473.115
• InChiKey: YATZMPAPKBNKEY-DTFRTGKBSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.25
• 重原子数：
  30.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110.38
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-O-benzyl-2-O-(tridec-1-yl)-3,4-O-isopropylidene-D-erythritol 在 盐酸 、 palladium on activated charcoal 、 氢气 、 溶剂黄146 、 三苯基膦 、 tetrafluoroboric acid dimethyl ether complex 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 22.5h， 生成 1,4-dideoxy-1,4-[(R)-[4-deoxy-2-O-(1-tridecyl)-D-erythritol-4-yl]episulfoniumylidene]-D-arabitol chloride
  参考文献：
  名称：

  Hydrophobic substituents increase the potency of salacinol, a potent α-glucosidase inhibitor from Ayurvedic traditional medicine ‘Salacia’

  摘要：

  Using an in silico method, seven analogs bearing hydrophobic substituents (8a: Me, 8b: Et, 8c: n-Pent, 8d: n-Hept, 8e: n-Tridec, 8f: isoBu and 8g: neoPent) at the 3'-O-position in salacinol (1), a highly potent natural alpha-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia', were designed and synthesized. In order to verify the computational SAR assessments, their alpha-glucosidase inhibitory activities were evaluated in vitro. All analogs (8a-8g) exhibited an equal or considerably higher level of inhibitory activity against rat small intestinal alpha-glucosidases compared with the original sulfonate (1), and were as potent as or higher in potency than the clinically used anti-diabetics, voglibose, acarbose or miglitol. Their activities against human maltase exhibited good relationships to the results obtained with enzymes of rat origin. Among the designed compounds, the one with a 3'-O-neopentyl moiety (8g) was most potent, with an approximately ten fold increase in activity against human maltase compared to 1. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.06.013