4-(吡唑-1-基)苯乙酸乙酯 | 66956-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(吡唑-1-基)苯乙酸乙酯
• 英文名称: 4-(pyrazol-1-yl)phenylacetic acid ethyl ester
• 英文别名: ethyl 2-(4-pyrazol-1-ylphenyl)acetate
• CAS: 66956-13-6
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: NZBNLWBOJSOSRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：

  4-(吡唑-1-基)苯乙酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以78%的产率得到2-(4-Pyrazol-1-ylphenyl)acetohydrazide
  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-吡唑基)苯甲酸甲酯 在 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 硫酸 、 calcium chloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 53.0h， 生成 4-(吡唑-1-基)苯乙酸乙酯
  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

• Pyrazol-1-ylphenylacetic acids
  申请人：Byk Gulden Lomberg Chemische Fabrik GmbH

  公开号：US04239901A1

  公开（公告）日：1980-12-16

  Pyrazol-1-ylphenylacetic acids of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are the same or different and denote a hydrogen atom or a halogen atom, R.sup.4 denotes a hydrogen atom or an alkyl group, A B denotes a carbon-carbon single or double bond, and their salts are pharmacologically active and are useful as medicaments. Medicament compositions are produced therefrom. Their functional carboxylic acid derivatives and other new intermediates are used in their preparation.

  Pyrazol-1-ylphenylacetic acids的中文翻译为：吡唑-1-基苯乙酸。其中R.sup.1，R.sup.2和R.sup.3相同或不同，表示氢原子或卤素原子，R.sup.4表示氢原子或烷基，AB表示碳-碳单键或双键，它们的盐具有药理活性，并且可用作药物。从中制备药物组合物。它们的功能性羧酸衍生物和其他新中间体用于它们的制备。
• N-substituted piperidine derivatives as serotonin receptor agents
  申请人：Andersson Carl-Magnus

  公开号：US20060094758A1

  公开（公告）日：2006-05-04

  Disclosed herein are compounds of Formula I, or a pharmaceutically acceptable salt, amide, ester, or prodrug thereof. Also disclosed are methods of inhibiting an activity of a monoamine receptor comprising contacting the monoamine receptor or a system containing the monoamine receptor with an effective amount of one or more of the compounds of Formula I. Disclosed are also methods of inhibiting an activation of a monoamine receptor comprising contacting the monoamine receptor or a system containing the monoamine receptor with an effective amount of one or more of the compounds of Formula I. Furthermore, methods of treating psychotic disease using a compound of Formula I are disclosed.

  本文披露了公式I的化合物，或其药学上可接受的盐、酰胺、酯或前药。还披露了抑制单胺受体活性的方法，包括将单胺受体或含有单胺受体的系统与公式I的一种或多种化合物的有效量接触。还披露了抑制单胺受体激活的方法，包括将单胺受体或含有单胺受体的系统与公式I的一种或多种化合物的有效量接触。此外，本文还披露了使用公式I的化合物治疗精神疾病的方法。
• [EN] N-SUBSTITUTED PIPERIDINE DERIVATIVES AS SEROTONIN RECEPTOR AGENTS<br/>[FR] DERIVES DE PIPERIDINE SUBSTITUES EN N EN TANT QU'AGENTS RECEPTEURS DE LA SEROTONINE
  申请人：ACADIA PHARM INC

  公开号：WO2004000808A3

  公开（公告）日：2004-03-25
• US4239901A
  申请人：——

  公开号：US4239901A

  公开（公告）日：1980-12-16
• US7253186B2
  申请人：——

  公开号：US7253186B2

  公开（公告）日：2007-08-07