(E)-3-(4-tert-butyl-phenyl)-2-phenyl-acrylic acid | 840526-97-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-3-(4-tert-butyl-phenyl)-2-phenyl-acrylic acid
• 英文别名: (E)-3-(4-tert-butylphenyl)-2-phenylprop-2-enoic acid
• CAS: 840526-97-8
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: PESVDMSHMHWVJF-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-氨基-1,4-苯并二氧杂环 、 (E)-3-(4-tert-butyl-phenyl)-2-phenyl-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 3-(4-tert-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-phenylacrylamide
  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：

  苯乙酸 、 对叔丁基苯甲醛 在 乙酸酐 、 三乙胺 作用下， 以73%的产率得到(E)-3-(4-tert-butyl-phenyl)-2-phenyl-acrylic acid
  参考文献：
  名称：

  WO2006/101318

  摘要：

  公开号：

文献信息

• NOVEL COMPOUNDS, ISOMER THEREOF, OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF AS VANILLOID RECEPTOR ANTAGONIST; AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
  申请人：Kim Hee-Doo

  公开号：US20090105258A1

  公开（公告）日：2009-04-23

  This present invention relates to novel compounds, isomer thereof or pharmaceutically acceptable salt thereof as vanilloid receptor (Vanilloid Receptor 1; VR1; TRRPV1) antagonist; and a pharmaceutical composition containing the same. The present invention provides a pharmaceutical composition for preventing or treating a disease such as pain, migraine, arthralgia, neuralgia, neuropathies, nerve injury, skin disorder, urinary bladder hypersensitiveness, irritable bowel syndrome, fecal urgency, a respiratory disorder, irritation of skin, eye or mucous membrane, stomach-duodenal ulcer, inflammatory diseases, ear disease, and heart disease.

  本发明涉及一种新型化合物，其异构体或药物可接受的盐作为vanilloid受体（Vanilloid Receptor 1；VR1；TRRPV1）拮抗剂；以及含有该化合物的药物组合物。本发明提供了一种用于预防或治疗疾病，如疼痛，偏头痛，关节痛，神经痛，神经病，神经损伤，皮肤疾病，膀胱过敏，肠易激综合征，大便紧急，呼吸系统疾病，皮肤，眼或黏膜刺激，胃十二指肠溃疡，炎症性疾病，耳病和心脏病的药物组合物。
• WO2006/101318
  申请人：——

  公开号：——

  公开（公告）日：——
• NOVEL COMPOUNDS OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF AS VANILLOID RECEPTOR ANTAGONIST; AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
  申请人：Amorepacific Corporation

  公开号：EP1861357B1

  公开（公告）日：2013-04-24
• US7763657B2
  申请人：——

  公开号：US7763657B2

  公开（公告）日：2010-07-27
• [EN] NOVEL COMPOUNDS, ISOMER THEREOF, OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF AS VANILLOID RECEPTOR ANTAGONIST; AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME<br/>[FR] NOUVEAUX COMPOSES, ISOMERE DE CEUX-CI, OU SELS DE CEUX-CI ACCEPTABLES SUR LE PLAN PHARMACEUTIQUE UTILISES EN TANT QU'ANTAGONISTES DE RECEPTEUR VANILLOIDE; ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CES COMPOSES
  申请人：AMOREPACIFIC CORP

  公开号：WO2006101318A1

  公开（公告）日：2006-09-28

  [EN] This present invention relates to novel compounds, isomer thereof or pharmaceutically acceptable salts thereof as vanilloid receptor (Vanilloid Receotor 1; VR1; TRPV1 )antagonist; and a pharmaceutical composition containing the same. The present invention provides a pharmaceutical composition for preventing or treating a disease such as pain, migraine, arthralgia, neuralgia, neuropathies, nerve injury, skin disorder, urinary bladder hypersensitiveness, irritable bowel syndrome, fecal urgency, a respiratory disorder, irritation of skin, eye or mucous membrane, stomach-duodenal ulcer, inflammatory diseases, ear disease, and heart disease.
  [FR] L'invention concerne de nouveaux composés, un isomère de ceux-ci ou des sels de ceux-ci acceptables sur le plan pharmaceutique utilisés en tant qu'antagoniste de récepteur vanilloïde (récepteur vanilloïde 1; VR1; TRPV1 ); et une composition pharmaceutique contenant ces composés. L'invention concerne également une composition pharmaceutique destinée à prévenir ou traiter une maladie telle que la douleur, la migraine, l'arthralgie, la névralgie, les neuropathies, les lésions nerveuses, les affections cutanées, l'hypersensibilité de la vessie, le syndrome du colon irritable, la défécation impérieuse, les troubles respiratoires, l'irritation de la peau, des yeux ou des muqueuses, l'ulcère gastro-duodénal, les maladies inflammatoires, les maladies de l'oreille, et les maladies cardiaques.