1-(naphthalen-2-ylmethyl)-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]indole | 1396260-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(naphthalen-2-ylmethyl)-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]indole
• CAS: 1396260-51-7
• 化学式: C₄₅H₄₁NO₄
• 分子量: 659.825
• InChiKey: VDQGOQDKBJARPC-VPQGMAAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(naphthalen-2-ylmethyl)-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]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 1-(2-naphthylmethyl)-3-(β-D-xylopyranosyl)-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
• 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 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 1-(naphthalen-2-ylmethyl)-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]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.