1-(4-methoxybenzyl)imidazole-2-carboxaldehyde oxime | 95460-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxybenzyl)imidazole-2-carboxaldehyde oxime
• 英文别名: N-[[1-[(4-methoxyphenyl)methyl]imidazol-2-yl]methylidene]hydroxylamine
• CAS: 95460-14-3
• 化学式: C₁₂H₁₃N₃O₂
• 分子量: 231.254
• InChiKey: PHPDQUAMFYUTOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzyl)imidazole-2-carboxaldehyde oxime 在 镍 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 4.5h， 生成 2-(aminomethyl)-1-(4-methoxybenzyl)imidazole
  参考文献：
  名称：

  Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site

  摘要：

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.

  DOI：

  10.1021/jm00164a051
• 作为产物：
  描述：

  1-p-methoxybenzyl-2-formylimidazole 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 反应 0.17h， 以68%的产率得到1-(4-methoxybenzyl)imidazole-2-carboxaldehyde oxime
  参考文献：
  名称：

  Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site

  摘要：

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.

  DOI：

  10.1021/jm00164a051

文献信息

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

  公开号：EP0125783A1

  公开（公告）日：1984-11-21

  Compounds of formula wherein Y is -H, -OH, -OCH3, -F, -CF3 or C1-4alkyl; X is -H, -OH, -OCH3, -F, -CF3 or C1-4alkyl, oranyaccessible combination thereof up to four substituents; R is -CO2H or -CH2NHR1; R' is -H, phenyl or benzyl; and, n is 0-4, intermediates and processes for their preparation, pharmaceutical compositions containing them and their use in the inhibition of dopamine β-hydroxylase in mammals are described.

  式中的化合物 式中 Y 是-H、-OH、-OCH3、-F、-CF3 或 C1-4 烷基； X 是-H、-OH、-OCH3、-F、- 或 C1-4 烷基，或最多四个取代基的任意可获得的组合； R 是-CO2H 或-CH2NHR1； R' 是-H、苯基或苄基；以及 n 为 0-4、 描述了中间体及其制备工艺、含有中间体的药物组合物以及它们在抑制哺乳动物体内多巴胺 β-羟化酶中的用途。
• US4532331A
  申请人：——

  公开号：US4532331A

  公开（公告）日：1985-07-30
• US4772723A
  申请人：——

  公开号：US4772723A

  公开（公告）日：1988-09-20
• US4863944A
  申请人：——

  公开号：US4863944A

  公开（公告）日：1989-09-05