3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]-1H-indole | 1396259-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]-1H-indole
• CAS: 1396259-53-2
• 化学式: C₃₄H₃₃NO₄
• 分子量: 519.64
• InChiKey: HWLUHEGSCHFWIQ-WNQXLSPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]-1H-indole 在 10% Pd/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 (2S,3R,4S,5R)-2-(1H-indol-3-yl)oxane-3,4,5-triol
  参考文献：
  名称：

  Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors

  摘要：

  Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors are the current focus on the indication for the management of hyperglycemia in diabetes. Here, a novel series of C-linked indolylxyloside-based inhibitors of SGLT2 has been discovered. Structure-activity relationship studies revealed that substituents at the 7-position of the indole moiety and a p-cyclopropylphenyl group in the distal position were necessary for optimum inhibitory activity. The pharmacokinetic study demonstrates that the most potent compound 1i is metabolically stable with a low clearance in rats. In further efficacy study, 1i is found to significantly lower blood glucose levels of streptozotocin (STZ)-induced diabetic rats. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.053
• 作为产物：
  描述：

  1-(4-methylphenyl)sulfonyl-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]indole 在 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 20.0h， 生成 3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]-1H-indole
  参考文献：
  名称：

  Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors

  摘要：

  Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors are the current focus on the indication for the management of hyperglycemia in diabetes. Here, a novel series of C-linked indolylxyloside-based inhibitors of SGLT2 has been discovered. Structure-activity relationship studies revealed that substituents at the 7-position of the indole moiety and a p-cyclopropylphenyl group in the distal position were necessary for optimum inhibitory activity. The pharmacokinetic study demonstrates that the most potent compound 1i is metabolically stable with a low clearance in rats. In further efficacy study, 1i is found to significantly lower blood glucose levels of streptozotocin (STZ)-induced diabetic rats. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.053

文献信息

• Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors
  作者：Chun-Hsu Yao、Jen-Shin Song、Chiung-Tong Chen、Teng-Kuang Yeh、Tsung-Chih Hsieh、Szu-Huei Wu、Chung-Yu Huang、Yu-Lin Huang、Min-Hsien Wang、Yu-Wei Liu、Chi-Hui Tsai、Chidambaram Ramesh Kumar、Jinq-Chyi Lee

  DOI：10.1016/j.ejmech.2012.06.053

  日期：2012.9

  Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors are the current focus on the indication for the management of hyperglycemia in diabetes. Here, a novel series of C-linked indolylxyloside-based inhibitors of SGLT2 has been discovered. Structure-activity relationship studies revealed that substituents at the 7-position of the indole moiety and a p-cyclopropylphenyl group in the distal position were necessary for optimum inhibitory activity. The pharmacokinetic study demonstrates that the most potent compound 1i is metabolically stable with a low clearance in rats. In further efficacy study, 1i is found to significantly lower blood glucose levels of streptozotocin (STZ)-induced diabetic rats. (C) 2012 Elsevier Masson SAS. All rights reserved.