(3-Cyclobutyloxyphenyl)boronic acid | 1352143-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3-Cyclobutyloxyphenyl)boronic acid
• CAS: 1352143-87-3
• 化学式: C₁₀H₁₃BO₃
• 分子量: 192.022
• InChiKey: MUPITWIHZCTISU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-Cyclobutyloxyphenyl)boronic acid 、 [4-[(2-cyano-3-hydroxypent-2-enoyl)amino]phenyl] trifluoromethanesulfonate 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 methyl 5-[(2-cyano-3-hydroxypent-2-enoyl)amino]-2-(3-cyclobutyloxyphenyl)benzoate
  参考文献：
  名称：

  Biaryl analogues of teriflunomide as potent DHODH inhibitors

  摘要：

  The structure-activity relationships of a novel series of biaryl dihydroorotate dehydrogenase (DHODH) inhibitors related to teriflunomide are disclosed. These biaryl derivatives were the result of structure-based design and proved to be potent DHODH inhibitors which in addition showed good antiproliferative activities on peripheral blood mononuclear cells and good efficacies in vivo in the rat adjuvant-induced-arthritis model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.052

文献信息

• Discovery of benzofuran propanoic acid GPR120 agonists: From uHTS hit to mechanism-based pharmacodynamic effects
  作者：Matthew Lombardo、Kate Bender、Clare London、Michael A. Plotkin、Melissa Kirkland、Joel Mane、Michele Pachanski、Wayne Geissler、John Cummings、Bahanu Habulihaz、Taro E. Akiyama、Jerry Di Salvo、Maria Madeira、Joanna Pols、Mary Ann Powles、Michael F. Finley、Eric Johnson、Thomas Roussel、Victor N. Uebele、Alejandro Crespo、Dennis Leung、Candice Alleyne、Dorina Trusca、Ying Lei、Andrew D. Howard、Feroze Ujjainwalla、James R. Tata、Christopher J. Sinz

  DOI：10.1016/j.bmcl.2016.10.054

  日期：2016.12

  mouse oral glucose tolerance test (oGTT). Further optimization gave rise to the benzofuran propanoic acid series (exemplified by compound 37), which demonstrated acute mechanism-based pharmacodynamic effects. The combination of in vivo efficacy and attractive rodent pharmacodynamic profiles suggests compounds generated from this series may afford attractive candidates for the treatment of Type 2 diabetes

  据报道，将芳氧基丁酸超高通量筛选（uHTS）转化为有效和选择性的G蛋白偶联受体120（GPR120）激动剂系列。uHTS hit 1表现出优于相关脂肪酸受体GPR40的出色的啮齿动物药代动力学特性和选择性，但仅具有中等的GPR120效力。优化“左手”芳基可得到化合物6，该化合物在小鼠口服葡萄糖耐量试验（oGTT）中显示出基于GPR120机制的药效作用。进一步优化产生了苯并呋喃丙酸系列（以化合物37为例），证明了其具有基于急性机理的药效学作用。