(E)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylic acid | 745053-01-4

• 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: (E)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylic acid
• 英文别名: (E)-2-(4-(methylsulfonyl)phenyl)-3-(tetrahydro-2H-pyran-4-yl)acrylic acid；(E)-2-(4-methanesulfinylphenyl)-3-(tetrahydropyran-4-yl)acrylic acid；(E)-2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)prop-2-enoic acid
• CAS: 745053-01-4
• 化学式: C₁₅H₁₈O₅S
• 分子量: 310.371
• InChiKey: INXMLFBJZKIDHL-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以100%的产率得到2-(4-甲基磺酰基苯基)-3-四氢吡喃-4-基-丙酸
  参考文献：
  名称：

  SAR, Pharmacokinetics, Safety, and Efficacy of Glucokinase Activating 2-(4-Sulfonylphenyl)-N-thiazol-2-ylacetamides: Discovery of PSN-GK1

  摘要：

  Allosteric activators of the glucose-sensing enzyme glucokinase (GK) are currently attracting much interest as potential antidiabetic therapies because they can achieve powerful blood glucose lowering through actions in multiple organs. Here, the optimization of a weakly active high-throughput screening hit to (2R)-2-(4-cyclopropanesulfonylphenyl)-N-(5-fluorothiazol-2-yl)-3-(tetrahydropyran-4-yl)propionamide (PSN-GK1), a potent GK activator with an improved pharmacokinetic and safety profile, is described. Following oral administration, this compound elicited robust glucose lowering in rats.

  DOI：

  10.1021/jm8003202
• 作为产物：
  描述：

  ethyl 2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以71 g的产率得到(E)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylic acid
  参考文献：
  名称：

  SAR, Pharmacokinetics, Safety, and Efficacy of Glucokinase Activating 2-(4-Sulfonylphenyl)-N-thiazol-2-ylacetamides: Discovery of PSN-GK1

  摘要：

  Allosteric activators of the glucose-sensing enzyme glucokinase (GK) are currently attracting much interest as potential antidiabetic therapies because they can achieve powerful blood glucose lowering through actions in multiple organs. Here, the optimization of a weakly active high-throughput screening hit to (2R)-2-(4-cyclopropanesulfonylphenyl)-N-(5-fluorothiazol-2-yl)-3-(tetrahydropyran-4-yl)propionamide (PSN-GK1), a potent GK activator with an improved pharmacokinetic and safety profile, is described. Following oral administration, this compound elicited robust glucose lowering in rats.

  DOI：

  10.1021/jm8003202

文献信息

• Highly enantioselective hydrogenation of α-aryl-β-substituted acrylic acids catalyzed by Ir-SpinPHOX
  作者：Yi Zhang、Zhaobin Han、Fuying Li、Kuiling Ding、Ao Zhang

  DOI：10.1039/b919902k

  日期：——

  The enantioselective hydrogenation of a series of challenging substrates, α-aryl-β-substituted acrylic acids, was realized with high efficiency and enantioselectivity (up to 96%) under the catalysis of Ir(I) complex of Spiro-based P,N ligand, SpinPHOX.

  在Spiro基P,N配体SpinPHOX的铱(I)配合物催化下，一系列具有挑战性的底物，即α-芳基-β-取代丙烯酸，实现了高效率和高对映选择性（高达96%）的对映选择性氢化反应。
• Tri(cyclo) substituted amide compounds
  申请人：——

  公开号：US20040181067A1

  公开（公告）日：2004-09-16

  Compounds of Formula (I): 1 or pharmaceutically acceptable salts thereof, are useful in the prophylactic and therapeutic treatment of hyperglycemia and diabetes.

  公式（I）化合物或其药学上可接受的盐，可用于预防和治疗高血糖和糖尿病。
• TRI(CYCLO) SUBSTITUTED AMIDE COMPOUNDS
  申请人：Fyfe Colin Thor Matthew

  公开号：US20070281946A1

  公开（公告）日：2007-12-06

  Compounds of Formula (I): or pharmaceutically acceptable salts thereof, are useful in the prophylactic and therapeutic treatment of hyperglycemia and diabetes.

  式（I）的化合物或其药学上可接受的盐，在预防和治疗高血糖和糖尿病方面是有用的。
• [EN] PHENYLACETAMIDES AND THEIR USE AS GLUCOKINASE MODULATORS<br/>[FR] COMPOSES D'AMIDES SUBSTITUES TRI(CYCLO)
  申请人：OSI PHARM INC

  公开号：WO2004072031A3

  公开（公告）日：2004-12-02
• PHENYLACETAMIDES AND THEIR USE AS GLUCOKINASE MODULATORS
  申请人：Prosidion Limited

  公开号：EP1594867A2

  公开（公告）日：2005-11-16