(4-(三氟甲基)吡啶-2-基)硼酸 | 870459-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (4-(三氟甲基)吡啶-2-基)硼酸
• 英文名称: 4-(trifluoromethyl)-2-pyridinylboronic acid
• 英文别名: (4-(Trifluoromethyl)pyridin-2-yl)boronic acid；[4-(trifluoromethyl)pyridin-2-yl]boronic acid
• CAS: 870459-90-8
• 化学式: C₆H₅BF₃NO₂
• mdl: MFCD08063026
• 分子量: 190.917
• InChiKey: KJFNGXQZOZOTHA-UHFFFAOYSA-N

物化性质

• 沸点：
  316.1±52.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (4-(三氟甲基)吡啶-2-基)硼酸 在 sodium hydroxide 、 copper diacetate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 1-(4-tert-Butyl-phenyl)-6-chloro-3-(4-trifluoromethyl-pyridin-2-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARγ partial agonists

  摘要：

  A series of novel aryl indole-2-carboxylic acids has been identified as potent selective PPAR gamma modulators. Their chemical synthesis and in vitro activities are discussed. Compound 5 was selected for in vivo testing in the db/db mouse model of type 2 diabetes and resulted in reduction of hyperglycemia at comparable plasma exposure when compared to rosiglitazone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.002

文献信息

• Synthesis and Structure−activity Relationships of Antitubercular 2-Nitroimidazooxazines Bearing Heterocyclic Side Chains
  作者：Hamish S. Sutherland、Adrian Blaser、Iveta Kmentova、Scott G. Franzblau、Baojie Wan、Yuehong Wang、Zhenkun Ma、Brian D. Palmer、William A. Denny、Andrew M. Thompson

  DOI：10.1021/jm901378u

  日期：2010.1.28

  Recently described biphenyl analogues Of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility.
• Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARγ partial agonists
  作者：James F. Dropinski、Taro Akiyama、Monica Einstein、Bahanu Habulihaz、Tom Doebber、Joel P. Berger、Peter T. Meinke、Guo Q. Shi

  DOI：10.1016/j.bmcl.2005.08.002

  日期：2005.11

  A series of novel aryl indole-2-carboxylic acids has been identified as potent selective PPAR gamma modulators. Their chemical synthesis and in vitro activities are discussed. Compound 5 was selected for in vivo testing in the db/db mouse model of type 2 diabetes and resulted in reduction of hyperglycemia at comparable plasma exposure when compared to rosiglitazone. (c) 2005 Elsevier Ltd. All rights reserved.