7-methyl-1-(4-methylphenyl)sulfonyl-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]indole | 1396259-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-methyl-1-(4-methylphenyl)sulfonyl-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]indole
• CAS: 1396259-49-6
• 化学式: C₄₂H₄₁NO₆S
• 分子量: 687.857
• InChiKey: ROZABERGOJGNBI-IRDAIUSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-methyl-1-(4-methylphenyl)sulfonyl-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]indole 在 10% Pd/C 、 氢气 、 caesium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 47.0h， 生成 1-(4-cyclopropylbenzyl)-7-methyl-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：

  7-甲基吲哚 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 、 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 8.67h， 生成 7-methyl-1-(4-methylphenyl)sulfonyl-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