(E)-[1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)-3-(3-methoxy-4-nitrophenyl)]propenone | 1365620-93-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-[1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)-3-(3-methoxy-4-nitrophenyl)]propenone
• 英文别名: (E)-3-(1-hydroxy-3H-2,1-benzoxaborol-6-yl)-1-(3-methoxy-4-nitrophenyl)prop-2-en-1-one
• CAS: 1365620-93-4
• 化学式: C₁₇H₁₄BNO₆
• 分子量: 339.112
• InChiKey: VOTGCDYRXCFKHZ-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-[1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)-3-(3-methoxy-4-nitrophenyl)]propenone 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以10.1%的产率得到(E)-[1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)-3-(4-amino-3-methoxyphenyl)]propenone
  参考文献：
  名称：

  Chalcone–Benzoxaborole Hybrid Molecules as Potent Antitrypanosomal Agents

  摘要：

  We report the novel chalcone-benzoxaborole hybrids and their structure-activity relationship against Trypanosoma brucei parasites. The 4-NH2 derivative 29 and 3-OMe derivative 43 were found to have excellent potency. The synergistic 4-NH2-3-OMe compound 49 showed an IC50 of 0.010 mu g/mL and resulted in 100% survival and zero parasitemia in a murine infection model, which represents one of the most potent compounds discovered to date from the benzoxaborole class that inhibit T. brucei growth.

  DOI：

  10.1021/jm2012408
• 作为产物：
  描述：

  2-溴四苯醌 在 盐酸 、 甲醇 、 锂硼氢 、 正丁基锂 、 氯化亚砜 、 对甲苯磺酸 、 三乙胺 、 乙酰氯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.33h， 生成 (E)-[1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)-3-(3-methoxy-4-nitrophenyl)]propenone
  参考文献：
  名称：

  Chalcone–Benzoxaborole Hybrid Molecules as Potent Antitrypanosomal Agents

  摘要：

  We report the novel chalcone-benzoxaborole hybrids and their structure-activity relationship against Trypanosoma brucei parasites. The 4-NH2 derivative 29 and 3-OMe derivative 43 were found to have excellent potency. The synergistic 4-NH2-3-OMe compound 49 showed an IC50 of 0.010 mu g/mL and resulted in 100% survival and zero parasitemia in a murine infection model, which represents one of the most potent compounds discovered to date from the benzoxaborole class that inhibit T. brucei growth.

  DOI：

  10.1021/jm2012408

文献信息

• Chalcone–Benzoxaborole Hybrid Molecules as Potent Antitrypanosomal Agents
  作者：Zhitao Qiao、Qi Wang、Fenglong Zhang、Zhongli Wang、Tana Bowling、Bakela Nare、Robert T. Jacobs、Jiong Zhang、Dazhong Ding、Yangang Liu、Huchen Zhou

  DOI：10.1021/jm2012408

  日期：2012.4.12

  We report the novel chalcone-benzoxaborole hybrids and their structure-activity relationship against Trypanosoma brucei parasites. The 4-NH2 derivative 29 and 3-OMe derivative 43 were found to have excellent potency. The synergistic 4-NH2-3-OMe compound 49 showed an IC50 of 0.010 mu g/mL and resulted in 100% survival and zero parasitemia in a murine infection model, which represents one of the most potent compounds discovered to date from the benzoxaborole class that inhibit T. brucei growth.