2-((3-(4-bromophenyl)-1-(2-(diethylamino)ethyl)-1H-pyrazol-5-yl)methoxy)ethyl methanesulfonate | 1357158-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-((3-(4-bromophenyl)-1-(2-(diethylamino)ethyl)-1H-pyrazol-5-yl)methoxy)ethyl methanesulfonate
• CAS: 1357158-13-4
• 化学式: C₁₉H₂₈BrN₃O₄S
• 分子量: 474.419
• InChiKey: BTHYPRBWWWPNPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  28.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  73.66
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-((3-(4-bromophenyl)-1-(2-(diethylamino)ethyl)-1H-pyrazol-5-yl)methoxy)ethyl methanesulfonate 、 2-((4-氟苄基)硫基)-6,7-二氢-3H-环戊二烯并[D]嘧啶-4(5H)-酮 在 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 2-(4-fluorobenzylthio)-1-(2-((3-(4-bromophenyl)-1-(2-(diethylamino)ethyl)-1H-pyrazol-5-yl)methoxy)-ethyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-4(5H)-one L-tartaric acid
  参考文献：
  名称：

  Design and Synthesis of Novel Pyrazole-based Lp-PLA2 Inhibitors

  摘要：

  AbstractA series of novel pyrazole‐based lipoprotein‐associated phospholipase A2 (Lp‐PLA2) inhibitors have been designed and synthetized by a variety of acetophenones via a 10‐step convergent approach. The synthetic approach is carefully optimized, and an unsuccessful alternative route is also discussed. The in vitro biological activity reveals that all the synthesized compounds are potent Lp‐PLA2 inhibitors with compound 13b being the most potent one (Lp‐PLA2, IC50=1.5 nmol/L).

  DOI：

  10.1002/cjoc.201180354
• 作为产物：
  描述：

  5-(4-溴-苯基)-1H-吡唑-3-羧酸乙酯 在 lithium aluminium tetrahydride 、 氢化钾 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 14.51h， 生成 2-((3-(4-bromophenyl)-1-(2-(diethylamino)ethyl)-1H-pyrazol-5-yl)methoxy)ethyl methanesulfonate
  参考文献：
  名称：

  Design and Synthesis of Novel Pyrazole-based Lp-PLA2 Inhibitors

  摘要：

  AbstractA series of novel pyrazole‐based lipoprotein‐associated phospholipase A2 (Lp‐PLA2) inhibitors have been designed and synthetized by a variety of acetophenones via a 10‐step convergent approach. The synthetic approach is carefully optimized, and an unsuccessful alternative route is also discussed. The in vitro biological activity reveals that all the synthesized compounds are potent Lp‐PLA2 inhibitors with compound 13b being the most potent one (Lp‐PLA2, IC50=1.5 nmol/L).

  DOI：

  10.1002/cjoc.201180354