N-([1,1'-biphenyl]-3-yl)-2-(4-hydroxy-3-methoxyphenyl)acetamide | 478400-72-5

• 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: N-([1,1'-biphenyl]-3-yl)-2-(4-hydroxy-3-methoxyphenyl)acetamide
• 英文别名: 4-hydroxy-3-methoxy-N-(3-phenylphenyl)phenylacetamide；2-(4-hydroxy-3-methoxyphenyl)-N-(3-phenylphenyl)acetamide
• CAS: 478400-72-5
• 化学式: C₂₁H₁₉NO₃
• 分子量: 333.387
• InChiKey: WSDUGFQZLCGJPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-([1,1'-biphenyl]-3-yl)-2-(4-hydroxy-3-methoxyphenyl)acetamide 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 N-([1,1'-biphenyl]-3-yl)-2-(3-methoxy-4-((4-((2-methoxyethyl)amino)-1,3,5-triazin-2-yl)oxy)phenyl)acetamide
  参考文献：
  名称：

  Cell-Based Selection Expands the Utility of DNA-Encoded Small-Molecule Library Technology to Cell Surface Drug Targets: Identification of Novel Antagonists of the NK3 Tachykinin Receptor

  摘要：

  DNA-encoded small-molecule library technology has recently emerged as a new paradigm for identifying ligands against drug targets. To date, this technology has been used with soluble protein targets that are produced and used in a purified state. Here, we describe a cell-based method for identifying small-molecule ligands from DNA-encoded libraries against integral membrane protein targets. We use this method to identify novel, potent, and specific inhibitors of NK3, a member of the tachykinin family of G-protein coupled receptors (GPCRs). The method is simple and broadly applicable to other GPCRs and integral membrane proteins. We have extended the application of DNA-encoded library technology to membrane-associated targets and demonstrate the feasibility of selecting DNA-tagged, small-molecule ligands from complex combinatorial libraries against targets in a heterogeneous milieu, such as the surface of a cell.

  DOI：

  10.1021/acscombsci.5b00124
• 作为产物：
  描述：

  3-氨基联苯 、 高香草酸 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到N-([1,1'-biphenyl]-3-yl)-2-(4-hydroxy-3-methoxyphenyl)acetamide
  参考文献：
  名称：

  Cell-Based Selection Expands the Utility of DNA-Encoded Small-Molecule Library Technology to Cell Surface Drug Targets: Identification of Novel Antagonists of the NK3 Tachykinin Receptor

  摘要：

  DNA-encoded small-molecule library technology has recently emerged as a new paradigm for identifying ligands against drug targets. To date, this technology has been used with soluble protein targets that are produced and used in a purified state. Here, we describe a cell-based method for identifying small-molecule ligands from DNA-encoded libraries against integral membrane protein targets. We use this method to identify novel, potent, and specific inhibitors of NK3, a member of the tachykinin family of G-protein coupled receptors (GPCRs). The method is simple and broadly applicable to other GPCRs and integral membrane proteins. We have extended the application of DNA-encoded library technology to membrane-associated targets and demonstrate the feasibility of selecting DNA-tagged, small-molecule ligands from complex combinatorial libraries against targets in a heterogeneous milieu, such as the surface of a cell.

  DOI：

  10.1021/acscombsci.5b00124

文献信息

• N-arylphenylacetamide derivatives and medicinal compositions containing the same
  申请人：——

  公开号：US20040248983A1

  公开（公告）日：2004-12-09

  N-Arylphenylacetamide derivatives represented by the following formula [I]: 1 (wherein R 1 is C 1-6 alkoxy, etc.; R 2 is hydrogen, —(CH 2 ) m —N(R 6 )(R 7 ) (m is an integer of from 1 to 4; R 6 is hydrogen, C 1-4 alkyl, etc., R 7 is hydrogen, etc.), etc.; R 3 is hydrogen, halogen, etc.; R 4 is C 6-10 alkyl, —Y—R 8 (Y is a single bond, C 1-6 alkylene, C 2-6 alkenylene, C 2-6 alkynylene, etc., R 8 is aryl, C 3-8 cycloalkyl, C 6-15 polycycloalkyl, etc.), etc.; R 5 is hydrogen, etc.; and X 1 is hydrogen), or pharmaceutically acceptable salts thereof or hydrates or solvates of the same, and a pharmaceutical composition containing the same. These compounds are useful as preventives and/or remedies giving no pain at the early stage of administration, which are efficacious in oral administration and have potent analgesic and antiinflammatory effects.

  下列式子所代表的N-Arylphenylacetamide衍生物[I]：1（其中R1是C1-6烷氧基等；R2是氢，-(CH2)m-N(R6)(R7)（m是从1到4的整数；R6是氢，C1-4烷基等，R7是氢等）等；R3是氢，卤素等；R4是C6-10烷基，-Y-R8（Y是单键，C1-6烷基，C2-6烯基，C2-6炔基等，R8是芳基，C3-8环烷基，C6-15多环烷基等）等；R5是氢等；X1是氢），或其药学上可接受的盐或其水合物或溶剂合物，以及含有它们的药物组成物。这些化合物在口服时具有强效的镇痛和抗炎作用，可用作早期给药时无痛的预防和/或治疗。
• N-ARYLPHENYLACETAMIDE DERIVATIVES AND MEDICINAL COMPOSITIONS CONTAINING THE SAME
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP1403235A1

  公开（公告）日：2004-03-31

  N-Arylphenylacetamide derivatives represented by the following formula [I]: (wherein R1 is C1-6 alkoxy, etc.; R2 is hydrogen, -(CH2)m-N(R6)(R7) (m is an integer of from 1 to 4; R6 is hydrogen, C1-4 alkyl, etc., R7 is hydrogen, etc.), etc.; R3 is hydrogen, halogen, etc.; R4 is C6-10 alkyl, -Y-R8 (Y is a single bond, C1-6 alkylene, C2-6 alkenylene, C2-6 alkynylene, etc., R8 is aryl, C3-8 cycloalkyl, C6-15 polycycloalkyl, etc.), etc.; R5 is hydrogen, etc.; and X1 is hydrogen), or pharmaceutically acceptable salts thereof or hydrates or solvates of the same, and a pharmaceutical composition containing the same. These compounds are useful as preventives and/or remedies giving no pain at the early stage of administration, which are efficacious in oral administration and have potent analgesic and antiinflammatory effects.

  下式[I]代表的 N-芳基苯乙酰胺衍生物： (其中 R1 是 C1-6 烷氧基等；R2 是氢、-(CH2)m-N(R6)(R7)（m 是 1 至 4 的整数；R6 是氢、C1-4 烷基等，R7 是氢等）等；R3 是氢、卤素等；R4 是 C6-10 烷基、-Y-R8（Y 是单键、C1-6 烯基、C2-6 烯基、C2-6 烯炔基等、R8为芳基、C3-8环烷基、C6-15多环烷基等）等；R5为氢等；X1为氢），或其药学上可接受的盐或其水合物或溶液，以及含有这些化合物的药物组合物。这些化合物可作为预防药物和/或治疗药物，用药初期无疼痛感，口服有效，并具有强效镇痛和抗炎作用。
• EP1403235
  申请人：——

  公开号：——

  公开（公告）日：——
• US7084176B2
  申请人：——

  公开号：US7084176B2

  公开（公告）日：2006-08-01
• Cell-Based Selection Expands the Utility of DNA-Encoded Small-Molecule Library Technology to Cell Surface Drug Targets: Identification of Novel Antagonists of the NK3 Tachykinin Receptor
  作者：Zining Wu、Todd L. Graybill、Xin Zeng、Michael Platchek、Jean Zhang、Vera Q. Bodmer、David D. Wisnoski、Jianghe Deng、Frank T. Coppo、Gang Yao、Alex Tamburino、Genaro Scavello、G. Joseph Franklin、Sibongile Mataruse、Katie L. Bedard、Yun Ding、Jing Chai、Jennifer Summerfield、Paolo A. Centrella、Jeffrey A. Messer、Andrew J. Pope、David I. Israel

  DOI：10.1021/acscombsci.5b00124

  日期：2015.12.14

  DNA-encoded small-molecule library technology has recently emerged as a new paradigm for identifying ligands against drug targets. To date, this technology has been used with soluble protein targets that are produced and used in a purified state. Here, we describe a cell-based method for identifying small-molecule ligands from DNA-encoded libraries against integral membrane protein targets. We use this method to identify novel, potent, and specific inhibitors of NK3, a member of the tachykinin family of G-protein coupled receptors (GPCRs). The method is simple and broadly applicable to other GPCRs and integral membrane proteins. We have extended the application of DNA-encoded library technology to membrane-associated targets and demonstrate the feasibility of selecting DNA-tagged, small-molecule ligands from complex combinatorial libraries against targets in a heterogeneous milieu, such as the surface of a cell.