3-[4-(methylsulfonyl)phenoxy]-5-[(3S)-tetrahydrofuran-3-yloxy]-N-1,3-thiazol-2-ylbenzamide | 1171816-98-0

• 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: 3-[4-(methylsulfonyl)phenoxy]-5-[(3S)-tetrahydrofuran-3-yloxy]-N-1,3-thiazol-2-ylbenzamide
• 英文别名: 3-(4-methylsulfonylphenoxy)-5-[(3S)-oxolan-3-yl]oxy-N-(1,3-thiazol-2-yl)benzamide
• CAS: 1171816-98-0
• 化学式: C₂₁H₂₀N₂O₆S₂
• 分子量: 460.532
• InChiKey: UQHVRVYGEAIGAH-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氨基噻唑 、 C₁₈H₁₈O₇S 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 为溶剂， 生成 3-[4-(methylsulfonyl)phenoxy]-5-[(3S)-tetrahydrofuran-3-yloxy]-N-1,3-thiazol-2-ylbenzamide
  参考文献：
  名称：

  Structure–activity relationships of 3,5-disubstituted benzamides as glucokinase activators with potent in vivo efficacy

  摘要：

  The optimization of our lead GK activator 2a to 3-[(1S)-2-hydroxy-1-methylethoxy]-5-[4-(methylsulfonyl) phenoxy]-N-1,3-thiazol-2-ylbenzamide (6g), a potent GK activator with good oral availability, is described, including to uncouple the relationship between potency and hydrophobicity. Following oral administration, this compound exhibited robust glucose lowering in diabetic model rodents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.040

文献信息

• Structure–activity relationships of 3,5-disubstituted benzamides as glucokinase activators with potent in vivo efficacy
  作者：Tomoharu Iino、Noriaki Hashimoto、Kaori Sasaki、Sumika Ohyama、Riki Yoshimoto、Hideka Hosaka、Takuro Hasegawa、Masato Chiba、Yasufumi Nagata、Jun-ichi Eiki、Teruyuki Nishimura

  DOI：10.1016/j.bmc.2009.04.040

  日期：2009.6

  The optimization of our lead GK activator 2a to 3-[(1S)-2-hydroxy-1-methylethoxy]-5-[4-(methylsulfonyl) phenoxy]-N-1,3-thiazol-2-ylbenzamide (6g), a potent GK activator with good oral availability, is described, including to uncouple the relationship between potency and hydrophobicity. Following oral administration, this compound exhibited robust glucose lowering in diabetic model rodents. (C) 2009 Elsevier Ltd. All rights reserved.