2-[4-(4-Bromo-phenyl)-pyridin-3-yl]-oxazolidin-4-one | 929804-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[4-(4-Bromo-phenyl)-pyridin-3-yl]-oxazolidin-4-one
• CAS: 929804-34-2
• 化学式: C₁₄H₁₁BrN₂O₂
• 分子量: 319.158
• InChiKey: OMHGEJLVIIFBLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[4-(4-Bromo-phenyl)-pyridin-3-yl]-oxazolidin-4-one 、 溴代异丁烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以43%的产率得到2-(4-(4-Bromophenyl)pyridin-3-yl)-3-isobutyloxazolidin-4-one
  参考文献：
  名称：

  Synthesis and SAR of novel 2-arylthiazolidinones as selective analgesic N-type calcium channel blockers

  摘要：

  A series of new N-type (Ca(v)2.2) calcium channel blockers derived from the 'hit' structures 2-(3-bromo-4-fluorophenyl)-3(2-pyridin-2-yiethyl)thiazolidin-4-one 9 and its 2-[4-(4-bromophenyl)pyridin-3-yl]-3-isobutyI analogue 10 is described. Extensive SAR studies using a range of synthetic approaches resulted in novel, patented compounds with IC50 values of up to 0.2 mu M in an in vitro IMR32 assay, and selectivities for N/L of up to 30-fold. The new compounds described have potential in treatment of neuropathic pain. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.098
• 作为产物：
  描述：

  4-溴苯乙酮 在 三氟化硼乙醚 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 66.0h， 生成 2-[4-(4-Bromo-phenyl)-pyridin-3-yl]-oxazolidin-4-one
  参考文献：
  名称：

  Synthesis and SAR of novel 2-arylthiazolidinones as selective analgesic N-type calcium channel blockers

  摘要：

  A series of new N-type (Ca(v)2.2) calcium channel blockers derived from the 'hit' structures 2-(3-bromo-4-fluorophenyl)-3(2-pyridin-2-yiethyl)thiazolidin-4-one 9 and its 2-[4-(4-bromophenyl)pyridin-3-yl]-3-isobutyI analogue 10 is described. Extensive SAR studies using a range of synthetic approaches resulted in novel, patented compounds with IC50 values of up to 0.2 mu M in an in vitro IMR32 assay, and selectivities for N/L of up to 30-fold. The new compounds described have potential in treatment of neuropathic pain. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.098