ethyl 4-(1-imidazolyl)phenylacetate | 143426-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-(1-imidazolyl)phenylacetate
• 英文别名: ethyl 2-(4-imidazol-1-ylphenyl)acetate
• CAS: 143426-66-8
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: MJURZYAGZCJKGA-UHFFFAOYSA-N

物化性质

• 沸点：
  368.6±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

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：

  ethyl 4-(1-imidazolyl)phenylacetate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以71%的产率得到4-(1H-Imidazol-1-yl)benzeneacetic acid hydrazide
  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
• 作为产物：
  描述：

  4-(1-咪唑基)苯甲酸乙酯 在 盐酸 、 sodium tetrahydroborate 、 硫酸 、 氢溴酸 、 calcium chloride 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 51.0h， 生成 ethyl 4-(1-imidazolyl)phenylacetate
  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

• 6-substituted pyrazolo (3,4-d)pyrimidin-4-ones and compositions and
  申请人：Sanofi Winthrop, Inc.

  公开号：US05656629A1

  公开（公告）日：1997-08-12

  6-Substituted pyrazolo[3,4 -d]pyrimidin-4-one derivatives, pharmaceutical compositions containing them and methods for effecting c-GMP-phosphodiesterase inhibition and for treating heart failure and/or hypertension.

  6-取代嘧啶并[3,4 -d]嘧啶-4-酮衍生物，含有它们的药物组合物以及用于影响c-GMP-磷酸二酯酶抑制和治疗心力衰竭和/或高血压的方法。
• 6-substituted pyrazolo[3,4-d]pyrimidin-4-ones and compositions and
  申请人：Sanofi

  公开号：US05977118A1

  公开（公告）日：1999-11-02

  6-Substituted pyrazolo[3,4-d]pyrimidin-4-one derivatives, pharmaceutical compositions containing them and methods for effecting c-GMP-phosphodiesterase inhibition and for treating heart failure and/or hypertension.

  6-取代的吡唑并[3,4-d]嘧啶-4-酮衍生物，包含它们的制药组合物及用于影响c-GMP-磷酸二酯酶抑制和治疗心力衰竭和/或高血压的方法。
• [EN] 6-SUBSTITUTED PYRAZOLO [3,4-d] PYRIMIDIN-4-ONES AND COMPOSITIONS AND METHODS OF USE THEREOF<br/>[FR] PYRAZOLO [3,4-d] PYRIMIDIN-4-ONE A SUBSTITUTION EN POSITION 6 ET LEURS COMPOSITIONS ET PROCEDES D'UTILISATION
  申请人：SANOFI WINTHROP, INC.

  公开号：WO1996028429A1

  公开（公告）日：1996-09-19

  (EN) 6-Substituted pyrazolo [3,4-d] pyrimidin-4-one derivatives, pharmaceutical compositions containing them and methods for a) effecting c-GMP-phosphodiesterase inhibition, b) treating heart failure and/or hypertension, c) reversing or reducing nitrate-induced tolerance and d) treating angina pectoris, congestive heart disease and myocardial infarction utilizing them.(FR) On décrit des dérivés de pyrazolo [3,4-d] pyrimidin-4-one à substitution en position 6, des compositions pharmaceutiques les contenant et des procédés les utilisant pour a) inhiber la c-GMP-phosphodiestérase, b) traiter l'insuffisance cardiaque et/ou l'hypertension, c) inverser ou réduire la tolérance induite par le nitrate et d) traiter l'angine de poitrine, les maladies cardiaques congestives et l'infarctus du myocarde.

  以下是英文文本和法文文本的翻译结果： 英文原文： 6-Substituted pyrazolo [3,4-d] pyrimidin-4-one derivatives, pharmaceutical compositions containing them and methods for a) effecting c-GMP-phosphodiesterase inhibition, b) treating heart failure and/or hypertension, c) reversing or reducing nitrate-induced tolerance and d) treating angina pectoris, congestive heart disease and myocardial infarction utilizing them. 法文原文： On décrit des dérivés de pyrazolo [3,4-d] pyrimidin-4-one à substitution en position 6, des compositions pharmaceutiques les contenant et des procédés les utilisant pour a) inhiber la c-GMP-phosphodiestérase, b) traiter l'insuffisance cardiaque et/ou l'hypertension, c) inverser ou réduire la tolérance induite par le nitrate et d) traiter l'angine de poitrine, les maladies cardiaques congestionnes et l'infarctus du myocarde. 中文翻译： 以下为中文版本： 6-位己基双吡straints- [ 双吡咯吡啶-4-酮] 导体及其药物组成的成分及其应用方法，包括： a) 连带摄取的 c-GMP-磷酸二酯酶抑制作用， b) 治疗心功能不全和/or 高血压， c) 对所受硝酸盐诱导耐受性的逆转或减少，以及 d) 治疗冠Justin闭塞、心力衰竭和心肌梗死的方法。 中文解释： 这段英文和法文文本主要描述了一种6-位被取代的双吡咯吡啶-4-酮衍生物，及其药用成分和应用方法。研究对象涉及磷酸二酯酶抑制、治疗心力衰竭和高血压、逆转或减少硝酸盐导致的耐受性，以及治疗冠心病、心力衰竭和心肌梗死。内容涉及化学合成、药物成分及其医学应用。
• 6-SUBSTITUTED PYRAZOLO 3,4-d] PYRIMIDIN-4-ONES AND COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：SANOFI PHARMACEUTICALS, INC.

  公开号：EP0813527A1

  公开（公告）日：1997-12-29
• EP0813527A4
  申请人：——

  公开号：EP0813527A4

  公开（公告）日：1998-09-09