3,4-anhydro-1-O-benzyl-2-O-ethyl-D-erythritol | 1310460-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-anhydro-1-O-benzyl-2-O-ethyl-D-erythritol
• 英文别名: (2R)-2-[(1S)-1-ethoxy-2-phenylmethoxyethyl]oxirane
• CAS: 1310460-67-3
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: XDZLILNSZSWXKZ-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-anhydro-1-O-benzyl-2-O-ethyl-D-erythritol 在 palladium on activated charcoal 、 氢气 、 溶剂黄146 、 tetrafluoroboric acid dimethyl ether complex 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 1,4-dideoxy-1,4-{(R)-[4-deoxy-3-O-ethyl-D-erythritol-4-yl]episulfoniumylidene}-D-arabinitol 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
• 作为产物：
  描述：

  1-O-benzyl-2-O-ethyl-D-erythritol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以76%的产率得到3,4-anhydro-1-O-benzyl-2-O-ethyl-D-erythritol
  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

文献信息

• Biological evaluation of 3′-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3′ position in the side chain on the α-glucosidase inhibitory activity
  作者：Genzoh Tanabe、Tetsu Otani、Wenying Cong、Toshie Minematsu、Kiyofumi Ninomiya、Masayuki Yoshikawa、Osamu Muraoka

  DOI：10.1016/j.bmcl.2011.02.109

  日期：2011.5

  Four analogs with 3'-O-alkyl groups (9a: CH(3), 9b: C(2)H(5), 9c: C(13)H(27) or 9d: CH(2)Ph) instead of the 3'-O-sulfate anion in salacinol (1), a naturally occurring potent alpha-glucosidase inhibitor, were synthesized by the coupling reaction of 1,4-dideoxy-1,4-epithio-D-arabinitols (18a and 18b) with appropriate epoxides (10a-10d). These analogs showed equal or considerably higher inhibitory activity against rat small intestinal alpha-glucosidases than the original sulfate (1), and one of them (9d) was found more potent than currently used alpha-glucosidase inhibitors as antidiabetics. Thus, introduction of a hydrophobic moiety at the C3' position of this new class of inhibitor was found beneficial for onset of stronger inhibition against these enzymes. (C) 2011 Elsevier Ltd. All rights reserved.