6-(benzyloxy)benzo[c][1,2]oxaborol-1(3H)-ol | 1222010-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(benzyloxy)benzo[c][1,2]oxaborol-1(3H)-ol
• 英文别名: 1-hydroxy-6-phenylmethoxy-3H-2,1-benzoxaborole
• CAS: 1222010-47-0
• 化学式: C₁₄H₁₃BO₃
• 分子量: 240.066
• InChiKey: NJMSRMRFYVWONL-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  404.8±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(benzyloxy)benzo[c][1,2]oxaborol-1(3H)-ol 在 palladium 10% on activated carbon 水 、 氢气 、 sodium hydride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 [2-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yloxy)]acetic acid
  参考文献：
  名称：

  [EN] BORON-CONTAINING SMALL MOLECULES AS ANTIPROTOZOAL AGENTS
  [FR] PETITES MOLÉCULES CONTENANT DU BORE COMME AGENTS ANTIPROTOZOAIRES

  摘要：

  本发明提供了具有以下通式的新颖化合物，这些化合物可用于治疗原虫感染，包含此类化物的药物组合物，以及这些化合物与至少一种其他治疗有效成分的组合。

  公开号：

  WO2011049971A1
• 作为产物：
  描述：

  (2-甲酰基-5-苯基甲氧基苯基)硼酸 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以97%的产率得到6-(benzyloxy)benzo[c][1,2]oxaborol-1(3H)-ol
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationship of Trypanosoma brucei Leucyl-tRNA Synthetase Inhibitors as Antitrypanosomal Agents

  摘要：

  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.

  DOI：

  10.1021/jm101225g

文献信息

• [EN] 1 -HYDROXY-BENZOOXABOROLES AS ANTIPARASITIC AGENTS<br/>[FR] 1-HYDROXY-BENZOOXABOROLES COMME AGENTS ANTIPARASITAIRES
  申请人：LILLY CO ELI

  公开号：WO2014149793A1

  公开（公告）日：2014-09-25

  Provided are compounds useful for controlling endoparasites both in animals and agriculture. Further provided are methods for controlling endoparasite infestations of an animal by administering an effective amount of a compound as described above, or a pharmaceutically acceptable salt thereof, to an animal, as well as formulations for controlling endoparasite infestations using the compounds described above or an acceptable salt thereof, and an acceptable carrier. The claimed compounds are described by the following Markush formula:A typical example for a compound according to above formula is: A typical example for a compound according to above formula is:

  提供了一些在动物和农业中控制内寄生虫的化合物。此外，还提供了一种通过向动物施用上述化合物或其药学上可接受的盐的有效量来控制动物内寄生虫侵染的方法，以及使用上述化合物或其可接受的盐以及可接受的载体来控制内寄生虫侵染的配方。所述的化合物由以下Markush公式描述：根据上述公式的化合物的典型示例是：
• [EN] BORON-CONTAINING SMALL MOLECULES AS ANTI-PROTOZOAL AGENTS<br/>[FR] PETITES MOLÉCULES CONTENANT DU BORE EN TANT QU'AGENTS ANTIPROTOZOAIRES
  申请人：ANACOR PHARMACEUTICALS INC

  公开号：WO2010045503A1

  公开（公告）日：2010-04-22

  This invention provides, among other things, novel compounds useful for treating protozoal infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.

  这项发明提供了用于治疗原虫感染的新型化合物，包含这些化合物的药物组合物，以及这些化合物与至少一种额外治疗有效剂的组合。
• Synthesis of Benzoxaboroles by <i>ortho</i>-Oxalkylation of Arylboronic Acids with Aldehydes/Ketones in the Presence of Brønsted Acids
  作者：Jing Zhao、Jiuxi Chen、Qing Xu、Huan Li

  DOI：10.1021/acs.orglett.1c00032

  日期：2021.3.19

  Herein we describe a simple and efficient synthesis of benzoxaboroles from arylboronic acids and aldehydes or ketones in the presence of a Brønsted acid. This method greatly simplifies the starting materials and reduces the number of reaction steps. The reaction can also be accomplished with acetals and ketals. The reaction has a wide substrate scope and high practicability.

  在本文中，我们描述了在布朗斯台德酸存在下由芳基硼酸和醛或酮简单有效地合成苯并硼硼烷的方法。该方法大大简化了起始原料并减少了反应步骤。该反应也可以用缩醛和缩酮来完成。该反应具有广泛的底物范围和高实用性。
• 一种苯并硼唑的合成方法
  申请人：温州大学

  公开号：CN112625056B

  公开（公告）日：2022-10-21

  本发明属于有机合成技术领域，具体涉及一种苯并硼唑的合成方法，在有机溶剂中，在强酸催化剂的条件下，式(A)与(B)所示化合物发生脱水缩合反应，制得式(C)所示化合物。采用本发明方法制备苯并硼唑所用的原料上式(A)和(B)所示化合物和反应溶剂均简单易得；反应步骤简单，仅需一步即可得到产物；反应原子经济性高，反应条件温和；反应适于大量制备。
• A divalent protecting group for benzoxaboroles
  作者：Brett VanVeller、Matthew R. Aronoff、Ronald T. Raines

  DOI：10.1039/c3ra44385j

  日期：——

  1-Dimethylamino-8-methylaminonaphthalene is put forth as a protecting group for benzoxaboroles. The ensuing complex is fluorescent, charge-neutral, highly stable under basic conditions, stable to anhydrous acid, and readily cleavable in aqueous acid to return the free benzoxaborole.

  1-Dimethylamino-8-methylaminonaphthalene 被用作苯并氧硼烷的保护基团。由此产生的复合物具有荧光性、电荷中性、在碱性条件下高度稳定、对无水酸稳定，并可在水酸中轻易裂解，生成游离的苯并氧硼烷。