(E)-3-(4-Pyrrol-1-yl-phenyl)-acrylic acid ethyl ester | 143426-71-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(4-Pyrrol-1-yl-phenyl)-acrylic acid ethyl ester
• 英文别名: Ethyl 4-(1-pyrrolyl)cinnamate；ethyl 3-(4-pyrrol-1-ylphenyl)prop-2-enoate
• CAS: 143426-71-5
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: QNYOUFPTSXYSGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-Pyrrol-1-yl-phenyl)-acrylic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 45.0 ℃ 、405.3 kPa 条件下， 反应 4.0h， 以99%的产率得到3-(4-Pyrrol-1-yl-phenyl)-propionic acid ethyl ester
  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-(1H-吡咯-1-基)苯基]甲醇 在 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (E)-3-(4-Pyrrol-1-yl-phenyl)-acrylic acid ethyl ester
  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

• Imidazo [1,2-a] pyridines and their pharmaceutical use
  申请人：Fujisawa Pharmaceutical Co., Ltd

  公开号：US05574042A1

  公开（公告）日：1996-11-12

  The invention relates to novel bradykinin antagonists of the formula: ##STR1## wherein R.sup.1 is halogen, R.sup.2 and R.sup.3 are each hydrogen, lower alkyl, halo(lower)alkyl or acyl, R.sup.4 is aryl having suitable substituent(s), or a heterocyclic group optionally having suitable substituent(s), Q is O or N--R.sup.11, in which R.sup.11 is hydrogen or acyl, and A is lower alkylene, and pharmaceutically acceptable salts thereof.

  该发明涉及一种新的布雷金因拮抗剂，其化学式为：##STR1## 其中R.sup.1为卤素，R.sup.2和R.sup.3分别为氢，低碳基，卤素（低）碳基或酰基，R.sup.4为具有适当取代基的芳基或可选具有适当取代基的杂环基，Q为O或N- R.sup.11，其中R.sup.11为氢或酰基，A为低碳基烷基，以及其药学上可接受的盐。
• Method of preparing certain 3-halo-imidazopyridines
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05750699A1

  公开（公告）日：1998-05-12

  The invention relates to bradykinin antagonists of the formula: ##STR1## wherein R.sup.1 is halogen, R.sup.2 and R.sup.3 are each hydrogen, lower alkyl, halo(lower)alkyl or acyl, R.sup.4 is aryl having suitable substituent(s), or a heterocyclic group optionally having suitable substituent(s), Q is O or N--R.sup.11, in which R.sup.11 is hydrogen or acyl, and A is lower alkylene, and pharmaceutically acceptable salts thereof.

  本发明涉及公式为：##STR1##的肽酶抑制剂，其中R.sup.1为卤素，R.sup.2和R.sup.3分别为氢、较低的烷基、卤化(较低)烷基或酰基，R.sup.4为具有适当取代基的芳基，或者为一个杂环基，该杂环基可选择具有适当的取代基，Q为O或N-R.sup.11，其中R.sup.11为氢或酰基，A为较低的烷基，以及其药学上可接受的盐。