(4-羟基-3-碘-5-甲氧基苯基)乙酸 | 1000841-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: (4-羟基-3-碘-5-甲氧基苯基)乙酸
• 英文名称: (4-hydroxy-3-iodo-5-methoxyphenyl)acetic acid
• 英文别名: 2-(4-Hydroxy-3-iodo-5-methoxyphenyl)acetic acid
• CAS: 1000841-74-6
• 化学式: C₉H₉IO₄
• 分子量: 308.073
• InChiKey: PPHAORGDJRCGCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-羟基-3-碘-5-甲氧基苯基)乙酸 、 4-叔-丁基苄胺 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 、 三乙胺 作用下， 以94%的产率得到N-(4-tert-butyl-benzyl)-2-(3-iodo-4-hydroxy-5-methoxyphenyl)acetamide
  参考文献：
  名称：

  Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin

  摘要：

  As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3-methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with K-i (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6'-iodononivamide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.001
• 作为产物：
  描述：

  高香草酸 在 ammonium hydroxide 、 碘 、 potassium iodide 、 盐酸 作用下， 以 水 为溶剂， 反应 0.66h， 以7%的产率得到(4-羟基-3-碘-5-甲氧基苯基)乙酸
  参考文献：
  名称：

  Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin

  摘要：

  As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3-methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with K-i (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6'-iodononivamide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.001

文献信息

• COMPOSITIONS AND METHODS FOR TREATING PAIN
  申请人：Warsaw Orthopedic, Inc.

  公开号：EP1890712A1

  公开（公告）日：2008-02-27
• Compositions and methods for treating pain
  申请人：Roy Josee

  公开号：US20060280718A1

  公开（公告）日：2006-12-14

  In the present invention, Applicants demonstrate the effect of a biomembrane sealing agent on the development of chronic pain following tissue injury as well as acute pain in a model of acute inflammation. Applicants demonstrate the ability of this class of agents referred to as “biomembrane sealing agents” to reduce the severity of hyperalgesia and allodynia following mechanical insult to the nervous system as well as their ability to reduce acute pain in a model of acute inflammation. Applicant describes the use of injectable or depot formulations of biomembrane sealing agent(s) for prophylactic treatment such as they could be administered after the insult (i.e. post-injury or post-surgery) but before the onset of acute or chronic pain. Alternatively, biomembrane sealing agents could be used to reduce the severity of acute or chronic pain after onset.
• Compositions and methods for treating a damaged cardiovascular element
  申请人：Roy Josee

  公开号：US20070012323A1

  公开（公告）日：2007-01-18

  In the present invention, the applicants describe methods and compositions of treating damaged cardiovascular elements and cardiovascular conditions including hypotension, atherosclerotic lesions, vulnerable plaque, and acute myocardial infarct. The applicants demonstrate the ability of a biomembrane sealing agent to accumulate on the walls of damaged blood vessels and help improving mean arterial pressure following tissue injury. The applicants describe the use of formulations comprising at least one biomembrane sealing agent and one bioactive agent for prophylactic treatment such as they could be administered concurrently to an invasive therapeutic intervention or after the insult (i.e. post-injury or post-surgery). Alternatively, these methods and compositions could be used to reduce the severity of cardiovascular diseases after onset.
• Devices and methods for detection of markers of axial pain with or without radiculopathy
  申请人：McKay William F.

  公开号：US20070287991A1

  公开（公告）日：2007-12-13

  The invention provides devices and related methods and composition useful for diagnosis and monitoring the pain generator(s) of axial pain with or without radiculopathy and methods for screening test compounds potentially useful for treating axial pain with or without radiculopathy. Alternatively, degenerated discs can be monitored and treated before occurrence of a pathological pain condition. Pain markers and markers of degenerating disc include markers of neuronal, vascular, immune and matrix elements.
• Methods of treating joint pain in a subject by using an anti-angiogenic agent
  申请人：Zanella John M.

  公开号：US20070293428A1

  公开（公告）日：2007-12-20

  A method for treating a joint pain in a subject comprising providing an effective amount of an anti-angiogenic agent to a synovial capsule adjacent to the joint.