3-((1H-咪唑-1-基)甲基)苯甲酸乙酯 | 143426-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-((1H-咪唑-1-基)甲基)苯甲酸乙酯
• 英文名称: ethyl 3-<(1H-imidazol-1-yl)methyl>benzoate
• 英文别名: Ethyl 3-(imidazol-1-ylmethyl)benzoate
• CAS: 143426-62-4
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: XNOSGDSVSOKKGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((1H-咪唑-1-基)甲基)苯甲酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到3-(1H-咪唑-1-基甲基)-苯甲醇
  参考文献：
  名称：

  4-苯基-1,4-二氢吡啶的咪唑-1-基和吡啶-3-基衍生物结合Ca2 +拮抗作用和血栓烷A2合酶抑制作用。

  摘要：

  合成了一系列在苯环上带有咪唑-1-基或吡啶-3-基的4-苯基-1,4-二氢吡啶衍生物，目的是结合Ca2 +拮抗作用和血栓烷A2（TxA2）合酶抑制作用。同一分子。这些化合物中的一些在体外显示出明显的联合的Ca2 +拮抗作用和TxA2合酶抑制作用，而其他化合物则仅显示一种单一活性。讨论了重要的单个或组合活动的结构要求。通过分子力学和半经验AM1计算，对1,4-二氢-2,6-二甲基-4- [3-（1H-咪唑-1-基）苯基] -3,5-吡啶二甲酸进行了理论构象分析，二乙酯（FCE 24265）和两个紧密的同类物。FCE 24265，它以IC50 = 1抑制大鼠全血中TxB2的产生。选择7 x 10（-7）M和拮抗的K +诱导的豚鼠主动脉收缩，IC50 = 6.0 x 10（-8）M，用于进一步的药理评估。我们的结果表明，该化合物在体外和体内均不如硝苯地平有效，但在体内具有良好的分布，可降低血压而

  DOI：

  10.1021/jm00072a017
• 作为产物：
  描述：

  3-氰基苄基溴 在 盐酸 、 硫酸 、 sodium carbonate 作用下， 以 氯仿 为溶剂， 反应 52.0h， 生成 3-((1H-咪唑-1-基)甲基)苯甲酸乙酯
  参考文献：
  名称：

  Aromatic hydrazides as specific inhibitors of bovine serum amine oxidase

  摘要：

  New hydrazides were synthesized in search for specific inhibitors of bovine serum amine oxidase: a series of benzoic and phenylacetic acid hydrazides containing the 1H-imidazol-1-yl or the 1H-imidazol-1-ylmethyl group as (o, m, p)-substituent in the phenyl ring; an analogous series of p-substituted phenylhydrazides with 5 or 6-membered heterocyclic ring as substituent, and a series of similar phenylpropionic hydrazides. The longer and more flexible phenylacetic hydrazides, and to a somewhat lesser extent the phenylpropionic ones, were better specific inhibitors of bovine serum amine oxidase than the benzoic hydrazides, which were also bound by the enzyme with high affinity, but at a slow rate. Derivatives with p- and m -substituents were more reactive than the o-substituted ones. The chemical nature of the substituent was less important than its position in the phenyl ring and the presence of methylene spacers. These data point to the presence of a hydrophobic site at short distance from the protein carbonyl cofactor, so that simultaneous interaction of the 2 ends of the inhibitor molecule can occur at the 2 sites. The presence of the hydrophobic site was confirmed by the capability of some molecule deprived of the hydrazidic group to act as mild inhibitors. All hydrazides were less reactive by 2-3 orders of magnitude towards pig kidney diamine oxidase and FAD-dependent monoamine oxidase from rat brain mitochondria, while the other compounds showed similar inhibition power against all proteins. The specificity for the bovine enzyme seems therefore to be related to the concerted action of the 2 moieties of the inhibitor molecule.

  DOI：

  10.1016/0223-5234(92)90005-l

文献信息

• Aromatic hydrazides as specific inhibitors of bovine serum amine oxidase
  作者：M Artico、R Silvestri、G Stefancich、L Avigliano、A Di Giulio、M Maccarrone、E Agostinelli、B Mondovi、L Morpurgo

  DOI：10.1016/0223-5234(92)90005-l

  日期：1992.4

  New hydrazides were synthesized in search for specific inhibitors of bovine serum amine oxidase: a series of benzoic and phenylacetic acid hydrazides containing the 1H-imidazol-1-yl or the 1H-imidazol-1-ylmethyl group as (o, m, p)-substituent in the phenyl ring; an analogous series of p-substituted phenylhydrazides with 5 or 6-membered heterocyclic ring as substituent, and a series of similar phenylpropionic hydrazides. The longer and more flexible phenylacetic hydrazides, and to a somewhat lesser extent the phenylpropionic ones, were better specific inhibitors of bovine serum amine oxidase than the benzoic hydrazides, which were also bound by the enzyme with high affinity, but at a slow rate. Derivatives with p- and m -substituents were more reactive than the o-substituted ones. The chemical nature of the substituent was less important than its position in the phenyl ring and the presence of methylene spacers. These data point to the presence of a hydrophobic site at short distance from the protein carbonyl cofactor, so that simultaneous interaction of the 2 ends of the inhibitor molecule can occur at the 2 sites. The presence of the hydrophobic site was confirmed by the capability of some molecule deprived of the hydrazidic group to act as mild inhibitors. All hydrazides were less reactive by 2-3 orders of magnitude towards pig kidney diamine oxidase and FAD-dependent monoamine oxidase from rat brain mitochondria, while the other compounds showed similar inhibition power against all proteins. The specificity for the bovine enzyme seems therefore to be related to the concerted action of the 2 moieties of the inhibitor molecule.
• Imidazol-1-yl and pyridin-3-yl derivatives of 4-phenyl-1,4-dihydropyridines combining Ca2+ antagonism and thromboxane A2 synthase inhibition
  作者：Paolo Cozzi、Germano Carganico、Domenico Fusar、Mauro Grossoni、Maria Menichincheri、Vittorio Pinciroli、Roberto Tonani、Fabrizio Vaghi、Patricia Salvati

  DOI：10.1021/jm00072a017

  日期：1993.10

  combined activities are discussed. Theoretical conformational analysis, by molecular mechanics and semiempirical AM1 calculations, was performed for 1,4-dihydro-2,6-dimethyl-4-[3-(1H-imidazol-1-yl)phenyl]- 3,5-pyridinedicarboxylic acid, diethyl ester (FCE 24265) and two close congeners. FCE 24265, which inhibited TxB2 production in rat whole blood with IC50 = 1.7 x 10(-7) M and antagonized K+ induced

  合成了一系列在苯环上带有咪唑-1-基或吡啶-3-基的4-苯基-1,4-二氢吡啶衍生物，目的是结合Ca2 +拮抗作用和血栓烷A2（TxA2）合酶抑制作用。同一分子。这些化合物中的一些在体外显示出明显的联合的Ca2 +拮抗作用和TxA2合酶抑制作用，而其他化合物则仅显示一种单一活性。讨论了重要的单个或组合活动的结构要求。通过分子力学和半经验AM1计算，对1,4-二氢-2,6-二甲基-4- [3-（1H-咪唑-1-基）苯基] -3,5-吡啶二甲酸进行了理论构象分析，二乙酯（FCE 24265）和两个紧密的同类物。FCE 24265，它以IC50 = 1抑制大鼠全血中TxB2的产生。选择7 x 10（-7）M和拮抗的K +诱导的豚鼠主动脉收缩，IC50 = 6.0 x 10（-8）M，用于进一步的药理评估。我们的结果表明，该化合物在体外和体内均不如硝苯地平有效，但在体内具有良好的分布，可降低血压而