N-(2,2-dimethoxyethyl)-3-(4-methoxyphenyl)propionamide | 95333-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(2,2-dimethoxyethyl)-3-(4-methoxyphenyl)propionamide
• 英文别名: N-(2,2-dimethoxyethyl)-3-(4-methoxyphenyl)propanamide
• CAS: 95333-86-1
• 化学式: C₁₄H₂₁NO₄
• mdl: MFCD17021482
• 分子量: 267.325
• InChiKey: QULRXACWWAXKID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,2-dimethoxyethyl)-3-(4-methoxyphenyl)propionamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 以52%的产率得到amino>acetaldehyde dimethyl acetal
  参考文献：
  名称：

  Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 1. Some 1-phenyl and 1-phenyl-bridged derivatives of imidazole-2-thione

  摘要：

  The synthesis and characterization of some 1-(phenylalkyl)imidazole-2-thiones as a novel class of "multisubstrate" inhibitors of dopamine beta-hydroxylase (DBH) are described. These inhibitors incorporate structural features that resemble both tyramine and oxygen substrates, and as evidenced by steady-state kinetics, they appear to bind both the phenethylamine binding site and the active site copper atom(s) in DBH. A series of structural congeners that incorporate different bridging chain lengths between the phenyl ring (dopamine mimic) and the imidazole-2-thione group (oxygen mimic) define the optimum distance for inhibitory potency and the likely intersite distance in the DBH active site. Additional bridging analogues were prepared to determine the active site bulk tolerance and the effects of heteroatom replacement.

  DOI：

  10.1021/jm00162a008
• 作为产物：
  描述：

  3-(4-甲氧基苯基)丙酸 在 吡啶 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 N-(2,2-dimethoxyethyl)-3-(4-methoxyphenyl)propionamide
  参考文献：
  名称：

  Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 1. Some 1-phenyl and 1-phenyl-bridged derivatives of imidazole-2-thione

  摘要：

  The synthesis and characterization of some 1-(phenylalkyl)imidazole-2-thiones as a novel class of "multisubstrate" inhibitors of dopamine beta-hydroxylase (DBH) are described. These inhibitors incorporate structural features that resemble both tyramine and oxygen substrates, and as evidenced by steady-state kinetics, they appear to bind both the phenethylamine binding site and the active site copper atom(s) in DBH. A series of structural congeners that incorporate different bridging chain lengths between the phenyl ring (dopamine mimic) and the imidazole-2-thione group (oxygen mimic) define the optimum distance for inhibitory potency and the likely intersite distance in the DBH active site. Additional bridging analogues were prepared to determine the active site bulk tolerance and the effects of heteroatom replacement.

  DOI：

  10.1021/jm00162a008

文献信息

• Intermediates useful in the preparation of dopamine-beta-hydroxylase inhibitors
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0308573A2

  公开（公告）日：1989-03-29

  Compounds of Structure (III) : in which Y' is -OCH3; X1 is -H, halogen, C1-4 alkyl, -CN, -N02, -S02NH2, -C02H, -CONH2, -CHO, -CH20H, -CF3, -OCH3, -SO2C1-4 alkyl, -SO2C1-4 fluoralkyl, or -CO2C1-4 alkyl; and useful as intermediates in the preparation of novel dopamine β-hydroxylase inhibitors.

  结构(III)的化合物 其中 Y' 为-OCH3；X1 为-H、卤素、C1-4 烷基、-CN、-N02、-S02NH2、-C02H、-CONH2、-CHO、-CH20H、-CF3、-OCH3、-SO2C1-4 烷基、-SO2C1-4 氟烷基或-CO2C1-4 烷基；可用作制备新型多巴胺 β-羟化酶抑制剂的中间体。
• FRAZEE, JAMES S.;KAISER, CARL
  作者：FRAZEE, JAMES S.、KAISER, CARL

  DOI：——

  日期：——
• Dopamine-beta-hydroxylase inhibitors
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0125783B1

  公开（公告）日：1989-01-04
• Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 1. Some 1-phenyl and 1-phenyl-bridged derivatives of imidazole-2-thione
  作者：Lawrence I. Kruse、Carl Kaiser、Walter E. DeWolf、James S. Frazee、Eleanor Garvey、Eileen L. Hilbert、Wayne A. Faulkner、Kathryn E. Flaim、John L. Sawyer、Barry A. Berkowitz

  DOI：10.1021/jm00162a008

  日期：1986.12

  The synthesis and characterization of some 1-(phenylalkyl)imidazole-2-thiones as a novel class of "multisubstrate" inhibitors of dopamine beta-hydroxylase (DBH) are described. These inhibitors incorporate structural features that resemble both tyramine and oxygen substrates, and as evidenced by steady-state kinetics, they appear to bind both the phenethylamine binding site and the active site copper atom(s) in DBH. A series of structural congeners that incorporate different bridging chain lengths between the phenyl ring (dopamine mimic) and the imidazole-2-thione group (oxygen mimic) define the optimum distance for inhibitory potency and the likely intersite distance in the DBH active site. Additional bridging analogues were prepared to determine the active site bulk tolerance and the effects of heteroatom replacement.