4-fluoro-1-[(4-methoxyphenyl)methyl]-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]indole | 1396260-54-0

• 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: 4-fluoro-1-[(4-methoxyphenyl)methyl]-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]indole
• CAS: 1396260-54-0
• 化学式: C₄₂H₄₀FNO₅
• 分子量: 657.782
• InChiKey: UWXHPVZIQAYKOI-IRDAIUSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-fluoro-1-[(4-methoxyphenyl)methyl]-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]indole 在 palladium 10% on activated carbon 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 以78%的产率得到4-fluoro-1-(4-methoxybenzyl)-3-(β-D-xylopyranosyl)-1Hindole
  参考文献：
  名称：

  NOVEL GLYCOSIDE COMPOUNDS

  摘要：

  式（I）的化合物：其中X、Y和Z在此处定义。还披露了与这些化合物相关的药物组合物和治疗方法。

  公开号：

  US20130157970A1
• 作为产物：
  描述：

  4-氟吲哚 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 、 溴 、 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 44.67h， 生成 4-fluoro-1-[(4-methoxyphenyl)methyl]-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

• NOVEL GLYCOSIDE COMPOUNDS
  申请人：National Health Research Institutes

  公开号：US20130157970A1

  公开（公告）日：2013-06-20

  Compounds of formula (I): wherein X, Y, and Z are defined herein. Also disclosed are pharmaceutical compositions and therapeutical methods related to these compounds.

  式（I）的化合物：其中X、Y和Z在此处定义。还披露了与这些化合物相关的药物组合物和治疗方法。
• 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.