2-(2,3,4,6-tetra-O-benzyl-5a-carba-β-D-gluco-pyranosyl)benzoic acid methyl ester | 875108-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3,4,6-tetra-O-benzyl-5a-carba-β-D-gluco-pyranosyl)benzoic acid methyl ester
• 英文别名: 2-(2,3,4,5-tetra-O-benzyl-5a-carba-β-D-glucopyranosyl)benzoic acid methyl ester
• CAS: 875108-95-5
• 化学式: C₄₃H₄₄O₇
• 分子量: 672.818
• InChiKey: YEGXUMMULFWTQR-PPTDLXGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  50.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-benzyl-5a-carba-β-D-gluco-pyranosyl)benzoic acid methyl ester 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以81%的产率得到2-(2,3,4,6-tetra-O-benzyl-5a-carba-β-D-glucopyranosyl)benzyl alcohol
  参考文献：
  名称：

  5a-Carba-β-d-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes

  摘要：

  5a-Carba-beta-D-glucopyranose derivatives were synthesized and identified as novel SGLT2-selective inhibitors. These inhibitors exhibited potent SGLT2 inhibition with high selectivity over SGLT1. Among the tested compounds, 6f indicated the most potent hSGLT2 inhibition and the highest selectivity over hSGLT1. Moreover, the pharmacokinetics data also showed that 6h, which had the same aglycon structure as sergliflozin-active (3-active), had a threefold longer half-life time (T(1/2)) than sergliflozin (3) with a high distribution volume in db/db mice. Subsequently, 6h lowered blood glucose levels as much as 3 and showed longer hypoglycemic action than 3 in db/db mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.005
• 作为产物：
  描述：

  carbocyclic 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 、 水杨酸甲酯 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以49%的产率得到2-(2,3,4,6-tetra-O-benzyl-5a-carba-β-D-gluco-pyranosyl)benzoic acid methyl ester
  参考文献：
  名称：

  5a-Carba-β-d-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes

  摘要：

  5a-Carba-beta-D-glucopyranose derivatives were synthesized and identified as novel SGLT2-selective inhibitors. These inhibitors exhibited potent SGLT2 inhibition with high selectivity over SGLT1. Among the tested compounds, 6f indicated the most potent hSGLT2 inhibition and the highest selectivity over hSGLT1. Moreover, the pharmacokinetics data also showed that 6h, which had the same aglycon structure as sergliflozin-active (3-active), had a threefold longer half-life time (T(1/2)) than sergliflozin (3) with a high distribution volume in db/db mice. Subsequently, 6h lowered blood glucose levels as much as 3 and showed longer hypoglycemic action than 3 in db/db mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.005

文献信息

• EP1783110
  申请人：——

  公开号：——

  公开（公告）日：——