(E)-3-(2-(piperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)acrylic acid | 1005171-51-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-3-(2-(piperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)acrylic acid
• 英文别名: (E)-3-[2-piperidin-1-yl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enoic acid
• CAS: 1005171-51-6
• 化学式: C₁₄H₁₅F₃N₂O₂
• 分子量: 300.281
• InChiKey: PDHQJNXUPUDDKW-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-氨基-1,4-苯并二氧杂环 、 (E)-3-(2-(piperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)acrylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (E)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[2-piperidin-1-yl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide
  参考文献：
  名称：

  Discovery of Potent, Orally Available Vanilloid Receptor-1 Antagonists. Structure−Activity Relationship of N-Aryl Cinnamides

  摘要：

  The vanilloid receptor-1 (TRPV1 or VR1) is a member of the transient receptor potential (TRP) family of ion channels and plays a role in regulating the function of sensory nerves. A growing body of evidence demonstrates the therapeutic potential of TRPV1 modulators: particularly in the management of pain. As a result of our screening efforts, we identified (E)-3-(4-tert-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamide (1): an antagonist that blocks the capsaicin-induced and pH-induced uptake of Ca-45(2+) in TRPV1-expressing Chinese hamster ovary cells with IC50 values of 17 +/- 5 and 150 +/- 80 nM, respectively. In this report.. we describe the synthesis and structure-activity relationship of a series of N-aryl cinnamides, the most potent of which (49a and 49b) exhibit good oral bioavailability in rats (F-oral = 39% and 17%. respectively).

  DOI：

  10.1021/jm049485i
• 作为产物：
  描述：

  2-氯-6-三氟甲基烟酸 在 氢氧化钾 、 lithium aluminium tetrahydride 、 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 68.5h， 生成 (E)-3-(2-(piperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)acrylic acid
  参考文献：
  名称：

  Discovery of Potent, Orally Available Vanilloid Receptor-1 Antagonists. Structure−Activity Relationship of N-Aryl Cinnamides

  摘要：

  The vanilloid receptor-1 (TRPV1 or VR1) is a member of the transient receptor potential (TRP) family of ion channels and plays a role in regulating the function of sensory nerves. A growing body of evidence demonstrates the therapeutic potential of TRPV1 modulators: particularly in the management of pain. As a result of our screening efforts, we identified (E)-3-(4-tert-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamide (1): an antagonist that blocks the capsaicin-induced and pH-induced uptake of Ca-45(2+) in TRPV1-expressing Chinese hamster ovary cells with IC50 values of 17 +/- 5 and 150 +/- 80 nM, respectively. In this report.. we describe the synthesis and structure-activity relationship of a series of N-aryl cinnamides, the most potent of which (49a and 49b) exhibit good oral bioavailability in rats (F-oral = 39% and 17%. respectively).

  DOI：

  10.1021/jm049485i

文献信息

• Substituted Spiro Compounds and Their Use for Producing Pain-Relief Medicaments
  申请人：Frank Robert

  公开号：US20080269271A1

  公开（公告）日：2008-10-30

  The present invention relates to substituted spiro compounds, to processes for preparing them, to medicaments comprising these compounds and to the use of these compounds for producing medicaments.

  本发明涉及替代螺环化合物，涉及制备这些化合物的方法，涉及含有这些化合物的药物以及利用这些化合物生产药物的用途。
• NOVEL BRONCHODILATING ALPHA, BETA-UNSATURATED ISOQUINOLINE AMIDES
  申请人：Dalence Maria

  公开号：US20100256101A1

  公开（公告）日：2010-10-07

  The invention relates to novel compounds having the general formula (I), and which compounds are useful to manufacture a medicament to treat a disorder or disease characterized by bronchoconstriction, e.g. COPD and asthma, and vasoconstriction, e.g. hypertension.

  本发明涉及具有一般式(I)的新化合物，这些化合物可用于制造治疗支气管收缩（例如COPD和哮喘）和血管收缩（例如高血压）等疾病或疾病的药物。
• Bronchodilating alpha, beta-unsaturated isoquinoline amides
  申请人：Respiratorius AB

  公开号：US08318768B2

  公开（公告）日：2012-11-27

  The invention relates to novel compounds having the general formula (I), and which compounds are useful to manufacture a medicament to treat a disorder or disease characterized by bronchoconstriction, e.g. COPD and asthma, and vasoconstriction, e.g. hypertension.

  该发明涉及具有一般式（I）的新化合物，这些化合物可用于制造治疗支气管收缩（例如COPD和哮喘）和血管收缩（例如高血压）等疾病或疾病的药物。
• SUBSTITUIERTE SPIRO-VERBINDUNGEN UND DEREN VERWENDUNG ZUR HERSTELLUNG VON ARZNEIMITTELN GEGEN SCHMERZ
  申请人：Grünenthal GmbH

  公开号：EP1888596B1

  公开（公告）日：2014-10-22
• US8318768B2
  申请人：——

  公开号：US8318768B2

  公开（公告）日：2012-11-27