5-Phenethyl-oxazole-4-carboxylic acid ethyl ester | 113697-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Phenethyl-oxazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-(2-phenylethyl)-1,3-oxazole-4-carboxylate
• CAS: 113697-86-2
• 化学式: C₁₄H₁₅NO₃
• mdl: MFCD16426776
• 分子量: 245.278
• InChiKey: WTXWMJAIOMVHKT-UHFFFAOYSA-N

物化性质

• 沸点：
  357.8±30.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Phenethyl-oxazole-4-carboxylic acid ethyl ester 在 盐酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 生成 2-Amino-5-nitro-6-(2-oxo-4-phenyl-butylamino)-3H-pyrimidin-4-one
  参考文献：
  名称：

  Lipophilic 5,6,7,8-tetrahydropterin substrates for phenylalanine hydroxylase (monkey brain), tryptophan hydroxylase (rat brain) and tyrosine hydroxylase (rat brain)

  摘要：

  DOI：

  10.1016/0223-5234(87)90265-0
• 作为产物：
  描述：

  异氰基乙酸乙酯 、 3-苯基丙酸 在 N,N'-羰基二咪唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以43.4%的产率得到5-Phenethyl-oxazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Structure–Activity Relationships of Benzimidazole-Based Glutaminyl Cyclase Inhibitors Featuring a Heteroaryl Scaffold

  摘要：

  Glutaminyl cyclase (hQC) has emerged as a new potential target for the treatment of Alzheimer's disease (AD). The inhibition of hQC prevents of the formation of the A beta(3(pE)-40,42) species which were shown to be of elevated neurotoidcity and are likely to act as a seeding core, leading to an accelerated formation of A beta-oligomers and fibrils. This work presents a new class of inhibitors of hQC, resulting from a pharmacophore-based screen. Hit molecules were identified, containing benzimidazole as the metal binding group connected to 1,3,4-oxadiazole as the central scaffold. The subsequent optimization resulted in benzimidazoly1-1,3,4-thiadiazoles and -1,2,3-triazoles with an inhibitory potency in the nanomolar range. Further investigation into the potential binding mode of the new compound classes combined molecular docking and site directed mutagenesis studies.

  DOI：

  10.1021/jm4001709

文献信息

• [EN] INHIBITORS OF GLUTAMINYL CYCLASE<br/>[FR] NOUVEAUX INHIBITEURS
  申请人：PROBIODRUG AG

  公开号：WO2011107530A3

  公开（公告）日：2011-11-10