1-(4-甲氧基苄基)咪唑-2-硫酮 | 95460-09-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(4-甲氧基苄基)咪唑-2-硫酮
• 中文别名: 1-(4-甲氧基苄基)-1H-咪唑-2-硫醇
• 英文名称: 1-(4-methoxybenzyl)-2-mercaptoimidazole
• 英文别名: (4-methoxybenzyl)-2-mercaptoimidazole；1-(4-methoxybenzyl)-1H-imidazole-2-thiol；3-[(4-methoxyphenyl)methyl]-1H-imidazole-2-thione
• CAS: 95460-09-6
• 化学式: C₁₁H₁₂N₂OS
• mdl: MFCD10689830
• 分子量: 220.295
• InChiKey: MKYOHTKSEDVAKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-甲氧基苄基)咪唑-2-硫酮 在 正丁基锂 、 镍 作用下， 以 乙醇 为溶剂， 反应 4.67h， 生成 1-(4-methoxybenzyl)imidazole-2-carboxylic acid
  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：

  (E)-N-(4-甲氧基亚苄基)-2,2-二甲氧基乙胺 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 1-(4-甲氧基苄基)咪唑-2-硫酮
  参考文献：
  名称：

  取代1-苄基咪唑-2-硫醇作为多巴胺β-羟化酶的有效和口服活性抑制剂。

  摘要：

  DOI：

  10.1021/jm00156a002

文献信息

• Dopamine-.beta.-hydroxylase inhibitors
  申请人：SmithKline Beecham Corporation

  公开号：US04992459A1

  公开（公告）日：1991-02-12

  Potent DBH inhibitors having the formula ##STR1## can be used to inhibit DBH activity in mammals.

  具有以下结构式##STR1##的强效DBH抑制剂可用于抑制哺乳动物中的DBH活性。
• 2-(aminoalkylthio)imidazoles as dopamine-.beta.-hydroxylase inhibitors
  申请人：SmithKline Beckman Corporation

  公开号：US04882348A1

  公开（公告）日：1989-11-21

  Potent dopamine-.beta.-hydroxylase inhibitors having the Formula ##STR1## that are useful to inhibit dopamine-.beta.-hydroxylase activity, pharmaceutical compositions including these inhibitors, and methods of using these inhibitors to inhibit dopamine-.beta.-hydroxylase activity in mannals. Also disclosed are novel intermediates useful in preparing the presently invented inhibitors.

  具有以下公式的有效多巴胺-β-羟化酶抑制剂##STR1##，用于抑制多巴胺-β-羟化酶活性，包括这些抑制剂的制药组合物，并使用这些抑制剂抑制哺乳动物中的多巴胺-β-羟化酶活性的方法。还揭示了用于制备目前发明的抑制剂的新型中间体。
• Intermediate to dopamine-.beta.-hydroxylase inhibitors
  申请人：SmithKline Beckman Corporation

  公开号：US04912226A1

  公开（公告）日：1990-03-27

  Potent dopamine-.beta.-hydroxylase inhibitors having the Formula ##STR1## that are useful to inhibit dopamine-.beta.-hydroxylase activity, pharmaceutical compositions including these inhibitors, and methods of using these inhibitors to inhibit dopamine-.beta.-hydroxylase activity in mammals. Also disclosed are novel intermediates useful in preparing the presently invented inhibitors.

  具有公式##STR1##的有效多巴胺-β-羟化酶抑制剂，可用于抑制哺乳动物中的多巴胺-β-羟化酶活性，包括这些抑制剂的制药组合物以及使用这些抑制剂抑制哺乳动物中的多巴胺-β-羟化酶活性的方法。还披露了用于制备目前发明的抑制剂的新型中间体。
• Ester prodrugs of dopamine-.beta.-hydroxylase, inhibitors, composition
  申请人：SmithKline Beckman Corporation

  公开号：US04743613A1

  公开（公告）日：1988-05-10

  Compounds having the formula: ##STR1## which are ester prodrugs of potent dopamine-.beta.-hydroxylase inhibitors and thus are useful to inhibit dopamine-.beta.-hydroxylase activity, pharmeceutical compositions including these compounds, and methods of using these compounds to inhibit dopamine-.beta.-hydroxylase activity in mammals.

  具有以下化学式的化合物：##STR1## 是有效的多巴胺-β-羟化酶抑制剂的酯类前药，因此可用于抑制哺乳动物中的多巴胺-β-羟化酶活性，包括这些化合物的药物组合物以及使用这些化合物抑制哺乳动物中的多巴胺-β-羟化酶活性的方法。
• Dopamine .beta.-hydroxylase inhibitors
  申请人：SmithKline Beckman Corporation

  公开号：US04772723A1

  公开（公告）日：1988-09-20

  Potent DBH Inhibitors having the formula: ##STR1## wherein R is --CO.sub.2 H or --CH.sub.2 NHR.sup.1 can be used to inhibit DBH activity in mammals.

  具有以下结构式的强效DBH抑制剂：##STR1## 其中R是--CO.sub.2 H或--CH.sub.2 NHR.sup.1可用于抑制哺乳动物中的DBH活性。