[2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-acetic acid tert-butyl ester | 195309-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: [2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-acetic acid tert-butyl ester
• CAS: 195309-02-5
• 化学式: C₂₆H₂₈N₂O₅
• 分子量: 448.519
• InChiKey: HZGVFLSRWZTEOF-ZMYMWAMOSA-N

物化性质

• 熔点：
  194-195 °C
• 沸点：
  677.1±55.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  76.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-acetic acid tert-butyl ester 在 甲酸 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(3-(trifluoromethyl)benzyl)-3-(4-isopropylpiperazin-1-yl)-3-oxo-2-((3S,4R)-2-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)-4-((E)-styryl)azetidin-1-yl)propanamide
  参考文献：
  名称：

  Azetidinones as vasopressin V1a antagonists

  摘要：

  The azetidinone LY307174 (1) was identified as a screening lead for the vasopressin V1a receptor (IC50 45 nM at the human V1a receptor) based on molecular similarity to ketoconazole (2), a known antagonist of the luteinizing hormone releasing hormone receptor. Structure-activity relationships for the series were explored to optimize receptor affinity and pharmacokinetic properties, resulting in compounds with K-i values < 1 nM and brain levels after oral dosing similar to 100-fold higher than receptor affinities.[GRAPHICS](c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.031
• 作为产物：
  描述：

  (S)-(+)-2-氧代-4-苯基-3-恶唑烷乙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 [2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-acetic acid tert-butyl ester
  参考文献：
  名称：

  Azetidinones as vasopressin V1a antagonists

  摘要：

  The azetidinone LY307174 (1) was identified as a screening lead for the vasopressin V1a receptor (IC50 45 nM at the human V1a receptor) based on molecular similarity to ketoconazole (2), a known antagonist of the luteinizing hormone releasing hormone receptor. Structure-activity relationships for the series were explored to optimize receptor affinity and pharmacokinetic properties, resulting in compounds with K-i values < 1 nM and brain levels after oral dosing similar to 100-fold higher than receptor affinities.[GRAPHICS](c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.031