3-bromo-5-[4-(methylsulfonyl)phenoxy]phenol | 1177420-07-3

• 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-bromo-5-[4-(methylsulfonyl)phenoxy]phenol
• 英文别名: 3-bromo-5-(4-methylsulfonylphenoxy)phenol
• CAS: 1177420-07-3
• 化学式: C₁₃H₁₁BrO₄S
• 分子量: 343.198
• InChiKey: KRFWCWFLXVPMJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  503.2±50.0 °C(Predicted)
• 密度：
  1.585±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-5-[4-(methylsulfonyl)phenoxy]phenol 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 6-[3-(4-methylsulfonylphenoxy)-5-propan-2-yloxyphenyl]-1H-pyrazin-2-one
  参考文献：
  名称：

  Pyrimidone-based series of glucokinase activators with alternative donor–acceptor motif

  摘要：

  Glucokinase activators are a class of experimental agents under investigation as a therapy for Type 2 diabetes mellitus. An X-ray crystal structure of a modestly potent agent revealed the potential to substitute the common heterocyclic amide donor-acceptor motif for a pyridone moiety. We have successfully demonstrated that both pyridone and pyrimidone heterocycles can be used as a potent donor-acceptor substituent. Several sub-micromolar analogs that possess the desired partial activator profile were synthesized and characterized. Unfortunately, the most potent activators suffered from sub-optimal pharmacokinetic properties. Nonetheless, these donor-acceptor motifs may find utility in other glucokinase activator series or beyond. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.036
• 作为产物：
  描述：

  1-bromo-3-methoxy-5-[4-(methylsulfonyl)phenoxy]benzene 在 三溴化硼 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到3-bromo-5-[4-(methylsulfonyl)phenoxy]phenol
  参考文献：
  名称：

  NOVEL PHENYLPYRROLE DERIVATIVE

  摘要：

  公开号：

  EP2239253B1

文献信息

• Phenylpyrrole derivative
  申请人：Daiichi Sankyo Company, Limited

  公开号：US08017610B2

  公开（公告）日：2011-09-13

  The present invention relates to a compound or a pharmacologically acceptable salt thereof having superior glucokinase activating activity, and is a compound represented by general formula (I), or pharmacologically acceptable salt thereof: [wherein, A represents, for example, an oxygen atom or sulfur atom, R1 represents, for example, a C1-C6 alkyl group, a C1-C6 alkoxy group or a C1-C6 halogenated alkyl group, A and R1 together with the carbon atom bonded thereto form a heterocyclic group that may be substituted with 1 to 3 group(s) independently selected from Substituent Group α, R2 represents a phenyl group that may be substituted with 1 to 5 group(s) independently selected from Substituent Group α or a heterocyclic group that may be substituted with 1 to 3 group(s) independently selected from Substituent Group α, R3 represents a hydroxy group or a C1-C6 alkoxy group, and Substituent Group α consists of, for example, a halogen atom, a C1-C6 alkyl group, a C1-C6 alkyl group substituted with 1 or 2 hydroxy group(s), a C1-C6 alkylsulfonyl group, and a group represented by the formula —V—NR5R6 (wherein, V represents a carbonyl group or a sulfonyl group, and R5 and R6 may be the same or different and respectively represent a hydrogen atom or a C1-C6 alkyl group, or R5 and R6 together with the nitrogen atom bonded thereto form a 4- to 6-membered saturated heterocycle that may be substituted with 1 or 2 group(s) independently selected from a C1-C6 alkyl group and a hydroxy group, and the 4- to 6-membered saturated heterocycle may further contain one oxygen atom or nitrogen atom)].

  本发明涉及一种具有优越的葡萄糖激酶激活活性的化合物或其药理学上可接受的盐，该化合物由通式（I）表示，或其药理学上可接受的盐：[其中，A代表例如氧原子或硫原子，R1代表例如C1-C6烷基、C1-C6烷氧基或C1-C6卤代烷基，A和R1与其结合的碳原子形成可能被1到3个独立选择的取代基α取代的杂环基，R2代表可能被1到5个独立选择的取代基α取代的苯基或可能被1到3个独立选择的取代基α取代的杂环基，R3代表羟基或C1-C6烷氧基，取代基α由例如卤素原子、C1-C6烷基、带有1或2个羟基的C1-C6烷基、C1-C6烷基磺酰基和由公式—V—NR5R6表示的基组成（其中，V代表羰基或磺酰基，R5和R6可能相同或不同，分别代表氢原子或C1-C6烷基，或者R5和R6与其结合的氮原子形成可能被1或2个独立选择的C1-C6烷基和羟基取代的4-6环饱和杂环，4-6环饱和杂环还可能含有一个氧原子或氮原子）。
• US8017610B2
  申请人：——

  公开号：US8017610B2

  公开（公告）日：2011-09-13
• US8415359B2
  申请人：——

  公开号：US8415359B2

  公开（公告）日：2013-04-09
• Pyrimidone-based series of glucokinase activators with alternative donor–acceptor motif
  作者：Kevin J. Filipski、Angel Guzman-Perez、Jianwei Bian、Christian Perreault、Gary E. Aspnes、Mary T. Didiuk、Robert L. Dow、Richard F. Hank、Christopher S. Jones、Robert J. Maguire、Meihua Tu、Dongxiang Zeng、Shenping Liu、John D. Knafels、John Litchfield、Karen Atkinson、David R. Derksen、Francis Bourbonais、Ketan S. Gajiwala、Michael Hickey、Theodore O. Johnson、Paul S. Humphries、Jeffrey A. Pfefferkorn

  DOI：10.1016/j.bmcl.2013.06.036

  日期：2013.8

  Glucokinase activators are a class of experimental agents under investigation as a therapy for Type 2 diabetes mellitus. An X-ray crystal structure of a modestly potent agent revealed the potential to substitute the common heterocyclic amide donor-acceptor motif for a pyridone moiety. We have successfully demonstrated that both pyridone and pyrimidone heterocycles can be used as a potent donor-acceptor substituent. Several sub-micromolar analogs that possess the desired partial activator profile were synthesized and characterized. Unfortunately, the most potent activators suffered from sub-optimal pharmacokinetic properties. Nonetheless, these donor-acceptor motifs may find utility in other glucokinase activator series or beyond. (C) 2013 Elsevier Ltd. All rights reserved.
• NOVEL PHENYLPYRROLE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2239253B1

  公开（公告）日：2013-06-19