(E)-[3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-1-phenyl]propenone | 1195621-91-0

• 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)-[3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-1-phenyl]propenone
• 英文别名: (E)-3-(1-hydroxy-3H-2,1-benzoxaborol-7-yl)-1-phenylprop-2-en-1-one
• CAS: 1195621-91-0
• 化学式: C₁₆H₁₃BO₃
• 分子量: 264.088
• InChiKey: NTLCNDOBOCIIOH-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-7-carbaldehyde 、 苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 以27.6%的产率得到(E)-[3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-1-phenyl]propenone
  参考文献：
  名称：

  一种苯并硼唑7位查尔酮衍生物及其制备与应 用

  摘要：

  本发明涉及苯并硼唑7位查尔酮衍生物及其制备与应用，该衍生物的分子式为：，其合成包括以下步骤：在混合溶剂中加入和氢氧化钠或氢氧化钾，搅拌均匀后加入，搅拌反应后，用盐酸调节pH至酸性，过滤，所得滤饼用硅胶柱层析纯化，即得衍生物，该衍生物具有较强的抑制肿瘤细胞系增殖的活性，因此，此类化合物可以作为一类新型的抗肿瘤药物。

  公开号：

  CN108191898B

文献信息

• Design, Synthesis, and Structure−Activity Relationship of <i>Trypanosoma brucei</i> Leucyl-tRNA Synthetase Inhibitors as Antitrypanosomal Agents
  作者：Dazhong Ding、Qingqing Meng、Guangwei Gao、Yaxue Zhao、Qing Wang、Bakela Nare、Robert Jacobs、Fernando Rock、Michael R. K. Alley、Jacob J. Plattner、Guoqiang Chen、Dawei Li、Huchen Zhou

  DOI：10.1021/jm101225g

  日期：2011.3.10

  African trypanosomiasis, caused by the protozoal pathogen Tlypanosoma brucei (T. brucei), is one of the most neglected tropical diseases that are in great need of new drugs. We report the design and synthesis of T. bruceileucyl-tRNA synthetase (TbLeuRS) inhibitors and their structure activity relationship. Benzoxaborole was used as the core structure and C(6) was modified to achieve improved affinity bared on docking results that showed further binding space at this position. Indeed, compounds with C(7) substitutions showed diminished activity due to clash with the eukaryote specific I4ae helix while substitutions at C(6) gave enhanced affinity. TbLeuRS inhibitors with IC50 as low as 1.6 mu M were discovered, and the structure activity relationship was discussed. The most potent enzyme inhibitors also showed excellent T.brucei parasite growth inhibition activity. This is the first time that TbLeuRS inhibitors are reported, and this study suggests that leucyl-tRNA synthetase (LeuRS) could be a potential target for antiparasitic drug development.