(E)-3-Biphenyl-4-yl-N-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-acrylamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-Biphenyl-4-yl-N-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-acrylamide
• 英文别名: (E)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(4-phenylphenyl)prop-2-enamide
• 化学式: C₂₃H₁₉NO₃
• 分子量: 357.409
• InChiKey: KLGHLIUARUITQS-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2E)-3-(1,1'-biphenyl-4-yl)acrylic acid 、 6-氨基-1,4-苯并二氧杂环 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以13%的产率得到(E)-3-Biphenyl-4-yl-N-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-acrylamide
  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