3-(2-hydroxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-N-1,3-thiazol-2-ylbenzamide | 752238-88-3

• 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-(2-hydroxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-N-1,3-thiazol-2-ylbenzamide
• 英文别名: 5-(2-hydroxy-1-methylethoxy)-3-(4-methanesulfonylphenoxy)-N-thiazol-2-ylbenzamide；3-(1-hydroxypropan-2-yloxy)-5-(4-methylsulfonylphenoxy)-N-(2-thiazolyl)benzamide；3-(1-hydroxypropan-2-yloxy)-5-(4-methylsulfonylphenoxy)-N-(1,3-thiazol-2-yl)benzamide
• CAS: 752238-88-3
• 化学式: C₂₀H₂₀N₂O₆S₂
• 分子量: 448.521
• InChiKey: WXZJALPRVRLDDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-N-1,3-thiazol-2-ylbenzamide 以91.3 mg的产率得到3-[(1S)-2-hydroxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]-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
• 作为产物：
  描述：

  3-[1-[tert-butyl(dimethyl)silyl]oxypropan-2-yloxy]-5-(4-methylsulfonylphenoxy)-N-(1,3-thiazol-2-yl)benzamide 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以77%的产率得到3-(2-hydroxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-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

• Heteroarylcarbamoylbenzene derivative
  申请人：IIno Tomoharu

  公开号：US20060167053A1

  公开（公告）日：2006-07-27

  Compounds represented by formula (I): as well as their pharmaceutically acceptable salts are disclosed. The compounds are useful as glucokinase activating agents for the treatment of diabetes and related conditions. Compositions and methods of treatment are also included.

  公式（I）所代表的化合物及其药学上可接受的盐被披露。这些化合物可用作激活葡萄糖激酶的药剂，用于治疗糖尿病及相关疾病。还包括治疗组合物和方法。
• Heteroarylcarbamoylbenzene derivatives
  申请人：Iino Tomoharu

  公开号：US20090018056A1

  公开（公告）日：2009-01-15

  Compounds having glucokinase activating effects and being useful as treatments for diabetes, which are represented by the following formula (I): [wherein X 1 represents oxygen, etc., X 2 represents oxygen, etc., R 1 represents a group on Ring A such as alkylsulfonyl, etc., R 2 represents C3-7 cyclic alkyl optionally substituted with a halogen, etc., R 3 represents a substituent on Ring B such as lower alkyl, etc., formula (II): [Chemical Formula 1] represents 6- to 10-membered aryl, etc., and formula (III): [Formula 1] represents monocyclic or bicyclic heteroaryl optionally having on Ring B a substituent represented by R 3 above, wherein the carbon atom of Ring B which is bonded to the nitrogen atom of the amide group of formula (I) forms a C═N bond with the nitrogen atom of the ring], as well as their pharmaceutically acceptable salts.

  具有激活葡萄糖激酶效果且可用作糖尿病治疗的化合物，其化学式如下（I）：[其中X1代表氧等，X2代表氧等，R1代表环A上的基团，例如烷基磺酰等，R2代表C3-7环状烷基，可选择地被卤素等取代，R3代表环B上的取代基，例如低烷基等，化学式（II）：[化学式1]代表6到10成员芳基等，化学式（III）：[化学式1]代表单环或双环杂芳基，可选择地在环B上具有由上述R3代表的取代基，其中环B的碳原子与化学式（I）的酰胺基团的氮原子形成C═N键与环的氮原子结合]，以及其药学上可接受的盐。
• HETEROARYLCARBAMOYLBENZENE DERIVATIVE
  申请人：MSD K.K.

  公开号：EP1600442B1

  公开（公告）日：2018-01-17
• EP1992623A1
  申请人：——

  公开号：EP1992623A1

  公开（公告）日：2008-11-19
• US7432287B2
  申请人：——

  公开号：US7432287B2

  公开（公告）日：2008-10-07