4-{3-[(3aS,4S,5aR,9aR,9bR)-2,2,8,8-tetramethylhexahydro[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl]benzyl}phenol | 1383935-72-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-{3-[(3aS,4S,5aR,9aR,9bR)-2,2,8,8-tetramethylhexahydro[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl]benzyl}phenol
• 英文别名: 4-[3-((3aS,4S,5aR,9aR,9bR)-2,2,8,8-tetramethyl-hexahydro[1,3]dioxolo[4',5':3,4]benzo-, [1,2-d][1,3]dioxin-4-yl)benzyl]phenol
• CAS: 1383935-72-5
• 化学式: C₂₆H₃₂O₅
• 分子量: 424.537
• InChiKey: OUAKSPPZQGESFO-NZURDFQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-{3-[(3aS,4S,5aR,9aR,9bR)-2,2,8,8-tetramethylhexahydro[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl]benzyl}phenol 在 吡啶 、 4-二甲氨基吡啶 、 potassium phosphate 、 四(三苯基膦)钯 、 sodium bromide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.5h， 生成 (3aS,4S,5aR,9aR,9bR)-4-[3-(4-cyclopropylbenzyl)phenyl]-2,2,8,8-tetramethylhexahydro-3aH-[1,3]dioxolo[4',5':5,6]benzo[1,2-d][1,3]dioxin
  参考文献：
  名称：

  C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes

  摘要：

  C-Aryl 5a-carba-beta-D-glucopyranose derivatives were synthesized and evaluated for inhibition activity against hSGLT1 and hSGLT2. Modifications to the substituents on the two benzene rings resulted in enhanced hSGLT2 inhibition activity and extremely high hSGLT2 selectivity versus SGLT1. Using the created superimposed model, the reason for the high hSGLT2 selectivity was speculated to be that additional substituents occupied a new space, in a different way than known inhibitors. Among the tested compounds, the ethoxy compound 5h with high hSGLT2 selectivity exhibited more potent and longer hypoglycemic action in db/db mice than our O-carbasugar compound (1) and sergliflozin (2), which could be explained by its improved PK profiles relative to those of the two compounds. These results indicated that 5h might be a promising drug candidate for the treatment of type 2 diabetes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.053
• 作为产物：
  描述：

  (2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-1-[3-(4-(benzyloxy)benzyl)phenyl]-5-[(benzyloxy)methyl]cyclohexanol 在 20 % Pd(OH)2/C 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.5h， 生成 4-{3-[(3aS,4S,5aR,9aR,9bR)-2,2,8,8-tetramethylhexahydro[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl]benzyl}phenol
  参考文献：
  名称：

  C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes

  摘要：

  C-Aryl 5a-carba-beta-D-glucopyranose derivatives were synthesized and evaluated for inhibition activity against hSGLT1 and hSGLT2. Modifications to the substituents on the two benzene rings resulted in enhanced hSGLT2 inhibition activity and extremely high hSGLT2 selectivity versus SGLT1. Using the created superimposed model, the reason for the high hSGLT2 selectivity was speculated to be that additional substituents occupied a new space, in a different way than known inhibitors. Among the tested compounds, the ethoxy compound 5h with high hSGLT2 selectivity exhibited more potent and longer hypoglycemic action in db/db mice than our O-carbasugar compound (1) and sergliflozin (2), which could be explained by its improved PK profiles relative to those of the two compounds. These results indicated that 5h might be a promising drug candidate for the treatment of type 2 diabetes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.053

文献信息

• EP1783110
  申请人：——

  公开号：——

  公开（公告）日：——