C-(2-isobutoxy-6-trifluoromethyl-pyridin-3-yl)-methylamine | 935519-78-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: C-(2-isobutoxy-6-trifluoromethyl-pyridin-3-yl)-methylamine
• 英文别名: C-(2-isobutoxy-6-trifluoromethyl-pyridin-3-yl)-methylamin；[2-(2-methylpropoxy)-6-(trifluoromethyl)pyridin-3-yl]methanamine
• CAS: 935519-78-1
• 化学式: C₁₁H₁₅F₃N₂O
• mdl: MFCD24913441
• 分子量: 248.248
• InChiKey: LTPDGGLXIZVXLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  C-(2-isobutoxy-6-trifluoromethyl-pyridin-3-yl)-methylamine 、 1-oxo-1,2-dihydroisoquinolin-5-ylcarbamic acid phenyl ester 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 1-((2-isobutoxy-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(1-oxo-1,2-dihydroisoquinolin-5-yl)urea
  参考文献：
  名称：

  Discovery of Benzopyridone-Based Transient Receptor Potential Vanilloid 1 Agonists and Antagonists and the Structural Elucidation of Their Activity Shift

  摘要：

  Among a series of benzopyridone-based scaffolds investigated as human transient receptor potential vanilloid 1 (TRPV1) ligands, two isomeric benzopyridone scaffolds demonstrated a consistent and distinctive functional profile in which 2-oxo-1,2-dihydroquinolin-5-yl analogues (e.g., 2) displayed high affinity and potent antagonism, whereas 1-oxo-1,2-dihydroisoquinolin-5-yl analogues (e.g., 3) showed full agonism with high potency. Our computational models provide insight into the agonist-antagonist boundary of the analogues suggesting that the Arg557 residue in the S4-S5 linker might be important for sensing the agonist binding and transmitting signals. These results provide structural insights into the TRPV1 and the protein-ligand interactions at a molecular level.

  DOI：

  10.1021/acs.jmedchem.0c00982
• 作为产物：
  描述：

  2-氯-6-三氟甲基烟腈 在 dimethyl sulfide borane 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 C-(2-isobutoxy-6-trifluoromethyl-pyridin-3-yl)-methylamine
  参考文献：
  名称：

  Discovery of N-(1-(2-hydroxyethyl)quinolin-2-one)-N’-(1-phenyl-1H-pyrazol-5-yl)methyl) urea as Mode-Selective TRPV1 antagonist

  摘要：

  DOI：

  10.1016/j.bmcl.2024.129656

文献信息

• NOVEL VANILLOID RECEPTOR LIGANDS AND USE THEREOF FOR THE PRODUCTION OF PHARMACEUTICAL PREPARATIONS
  申请人：Lee Jeewoo

  公开号：US20070105861A1

  公开（公告）日：2007-05-10

  The present invention relates to novel vanilloid receptor ligands, to a process for the production thereof, to pharmaceutical preparations containing these compounds and to the use of these compounds for the production of pharmaceutical preparations.

  本发明涉及新型辣椒素受体配体，以及用于其生产的方法，含有这些化合物的药物制剂以及利用这些化合物生产药物制剂的用途。
• Neue Vanilloidrezeptor-Liganden und ihre Verwendung zur Herstellung von Arzneimitteln
  申请人：Grünenthal GmbH

  公开号：EP2388258A1

  公开（公告）日：2011-11-23

  Die vorliegende Erfindung betrifft neue Vanilloid-Rezeptor-Liganden, Verfahren zu ihrer Herstellung, Arzneimittel enthaltend diese Verbindungen und die Verwendung dieser Verbindungen zur Herstellung von Arzneimitteln.

  本发明涉及新型类香草素受体配体、其制备工艺、含有这些化合物的药物以及使用这些化合物制备药物。
• 2-(3-Fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists: Structure activity relationships of the 2-oxy pyridine C-region
  作者：Shivaji A. Thorat、Dong Wook Kang、HyungChul Ryu、Myeong Seop Kim、Ho Shin Kim、Jihyae Ann、Taehwan Ha、Sung-Eun Kim、Karam Son、Sun Choi、Peter M. Blumberg、Robert Frank、Gregor Bahrenberg、Klaus Schiene、Thomas Christoph、Jeewoo Lee

  DOI：10.1016/j.ejmech.2013.04.003

  日期：2013.6

  The structure activity relationships of 2-oxy pyridine derivatives in the C-region of N-(6-trifluoromethylpyridin-3-ylmethyl) 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as hTRPV1 antagonists were investigated. The analysis indicated that the lipophilicity of the 2-oxy substituents was critical for potent antagonism and 4 or 5 carbons appeared to be optimal for activity. Multiple compounds proved to have comparable activity to 1, which had been reported as the most potent antagonist for capsaicin activity among the previous series of compounds. Further analysis of compounds 22 (2-isobutyloxy) and 53 (2-benzyloxy) in the formalin test in mice demonstrated strong analgesic activity with full efficacy. Docking analysis of 535 using our hTRPV1 homology model indicated that the A- and B-region 2-(3fluoro-4-methylsulfonylaminophenyl)propanamide made important hydrophobic and hydrogen bonding interactions with Tyr511 and that the C-region 6-trifluoromethyl and 2-benzyloxy groups of pyridine occupied the two hydrophobic binding pockets, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.
• NEUE VANILLOID-REZEPTOR LIGANDEN UND IHRE VERWENDUNG ZUR HERSTELLUNG VON ARZNEIMITTELN
  申请人：Grünenthal GmbH

  公开号：EP1940821A2

  公开（公告）日：2008-07-09
• Novel Vanilloid Receptor Ligands and Use Thereof for the Production of Pharmaceutical Preparations
  申请人：Gruenenthal GmbH

  公开号：US20140179686A1

  公开（公告）日：2014-06-26

  The present invention relates to novel vanilloid receptor ligands, to a process for the production thereof, to pharmaceutical preparations containing these compounds and to the use of these compounds for the production of pharmaceutical preparations.