5-(4-cyclohexyl-piperazin-1-yl)-5-oxo-2-[2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-pentanoic acid | 512785-26-1

• 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: 5-(4-cyclohexyl-piperazin-1-yl)-5-oxo-2-[2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-pentanoic acid
• CAS: 512785-26-1
• 化学式: C₃₅H₄₂N₄O₆
• 分子量: 614.742
• InChiKey: UQCVYYJESHMJDO-QLTDWMCJSA-N

物化性质

• 沸点：
  896.4±65.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  110.7
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-(4-cyclohexyl-piperazin-1-yl)-5-oxo-2-[2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-pentanoic acid 、 3-氯苄胺 在 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 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-N-(3-chlorobenzyl)-5-(4-cyclohexylpiperazin-1-yl)-5-oxo-2-((3S,4R)-2-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)-4-((E)-styryl)azetidin-1-yl)pentanamide
  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：

  5-(4-cyclohexyl-piperazin-1-yl)-5-oxo-2-[2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-pentanoic acid tert-butyl ester 在 甲酸 作用下， 以92%的产率得到5-(4-cyclohexyl-piperazin-1-yl)-5-oxo-2-[2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-pentanoic acid
  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