2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide | 1428789-71-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide
• 英文别名: 2-[3-fluoro-4-(methanesulfonamidomethyl)phenyl]-N-[[2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl]methyl]propanamide
• CAS: 1428789-71-2
• 化学式: C₂₄H₃₀F₄N₄O₃S
• 分子量: 530.587
• InChiKey: ARMZBBXOPXFIEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.8
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N-[(4-bromo-2-fluorophenyl)methyl]methanesulfonamide 在 锰 、 bis(bipyridine)nickel(II) bromide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 45.0h， 生成 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide
  参考文献：
  名称：

  Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template

  摘要：

  A series of homologous analogues of prototype antagonist 1 and its urea surrogate were investigated as hTRPV1 ligands. Through one-carbon elongation in the respective pharmacophoric regions, N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea was identified as a novel and potent TRPV1 antagonistic template. Its representative compound 27 showed a potency comparable to that of lead compound 1. Docking analysis of compound 27 in our hTRPV1 homology model indicated that its binding mode was similar with that of 1S. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.06.010

文献信息

• [EN] AMINE SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS<br/>[FR] DÉRIVÉS DE MÉTHANESULFONAMIDE À SUBSTITUTION AMINE EN TANT QUE LIGANDS DES RÉCEPTEURS DES VANILLOÏDES
  申请人：GRUENENTHAL GMBH

  公开号：WO2013045451A1

  公开（公告）日：2013-04-04

  The invention relates to amine substituted methanesulfonamide derivatives of formula (I) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

  这项发明涉及公式（I）的胺取代甲磺酰胺衍生物作为辣椒素受体配体，涉及含有这些化合物的药物组合物，以及这些化合物用于治疗和/或预防疼痛以及其他疾病和/或紊乱。
• Amine Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
  申请人：Gruenenthal GmbH

  公开号：US20130079320A1

  公开（公告）日：2013-03-28

  The invention relates to amine substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

  这项发明涉及胺取代甲磺酰胺衍生物作为辣椒素受体配体，以及含有这些化合物的药物组合物，还涉及这些化合物用于治疗和/或预防疼痛以及其他疾病和/或紊乱。
• AMINE SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
  申请人：Grünenthal GmbH

  公开号：EP2760836A1

  公开（公告）日：2014-08-06
• US8765733B2
  申请人：——

  公开号：US8765733B2

  公开（公告）日：2014-07-01
• Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template
  作者：Jihyae Ann、Wei Sun、Xing Zhou、Aeran Jung、Jisoo Baek、Sunho Lee、Changhoon Kim、Suyoung Yoon、Sunhye Hong、Sun Choi、Noe A. Turcios、Brienna K.A. Herold、Timothy E. Esch、Nancy E. Lewin、Adelle Abramovitz、Larry V. Pearce、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmcl.2016.06.010

  日期：2016.8

  A series of homologous analogues of prototype antagonist 1 and its urea surrogate were investigated as hTRPV1 ligands. Through one-carbon elongation in the respective pharmacophoric regions, N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea was identified as a novel and potent TRPV1 antagonistic template. Its representative compound 27 showed a potency comparable to that of lead compound 1. Docking analysis of compound 27 in our hTRPV1 homology model indicated that its binding mode was similar with that of 1S. (C) 2016 Elsevier Ltd. All rights reserved.