(4S,5R)-5-(2-but-3-enyl-1,3-dioxolan-2-yl)-4-(cyclohexylmethyl)-1,3-oxazolidin-2-one | 134848-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-5-(2-but-3-enyl-1,3-dioxolan-2-yl)-4-(cyclohexylmethyl)-1,3-oxazolidin-2-one
• CAS: 134848-97-8
• 化学式: C₁₇H₂₇NO₄
• 分子量: 309.406
• InChiKey: PKORHKQXIURFGB-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  56.79
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-(2-but-3-enyl-1,3-dioxolan-2-yl)-4-(cyclohexylmethyl)-1,3-oxazolidin-2-one 在 RuO₂/C sodium periodate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以98%的产率得到3-[2-((4S,5R)-4-Cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-[1,3]dioxolan-2-yl]-propionic acid
  参考文献：
  名称：

  Design and synthesis of P2-P1'-linked macrocyclic human renin inhibitors

  摘要：

  Using a computer model of the active site of human renin developed at Merck, we designed a series of novel P2-P1'-linked, macrocyclic renin inhibitors 3-10. These unique inhibitors incorporate a transition-state isostere within a 13- or 14-membered ring. The three most active compounds in this family were 13-membered-ring glutamine-derived inhibitor 3, 14-membered-ring diaminopropionic acid derived inhibitor 6, and 13-membered-ring diol 9 (IC50 0.61, 0.59, 0.65-mu-M, respectively). Modification of inhibitor 3 at P4 led to 56 nM macrocyclic renin inhibitor 39. This study shows the viability of renin inhibitor designs which incorporate a scissile-bond replacement within a macrocycle.

  DOI：

  10.1021/jm00113a005
• 作为产物：
  描述：

  (4S,5R)-4-环己基甲基-2-恶唑烷酮-5-羧酸甲酯 在 三甲基铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 26.5h， 生成 (4S,5R)-5-(2-but-3-enyl-1,3-dioxolan-2-yl)-4-(cyclohexylmethyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Design and synthesis of P2-P1'-linked macrocyclic human renin inhibitors

  摘要：

  Using a computer model of the active site of human renin developed at Merck, we designed a series of novel P2-P1'-linked, macrocyclic renin inhibitors 3-10. These unique inhibitors incorporate a transition-state isostere within a 13- or 14-membered ring. The three most active compounds in this family were 13-membered-ring glutamine-derived inhibitor 3, 14-membered-ring diaminopropionic acid derived inhibitor 6, and 13-membered-ring diol 9 (IC50 0.61, 0.59, 0.65-mu-M, respectively). Modification of inhibitor 3 at P4 led to 56 nM macrocyclic renin inhibitor 39. This study shows the viability of renin inhibitor designs which incorporate a scissile-bond replacement within a macrocycle.

  DOI：

  10.1021/jm00113a005