6-(benzylamino)benzo[c][1,2]oxaborol-1(3H)-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(benzylamino)benzo[c][1,2]oxaborol-1(3H)-ol
• 英文别名: N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-benzamine；N-benzyl-1-hydroxy-3H-2,1-benzoxaborol-6-amine
• 化学式: C₁₄H₁₄BNO₂
• 分子量: 239.082
• InChiKey: LRBPMXBSPAREEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 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：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(benzylamino)benzo[c][1,2]oxaborol-1(3H)-ol 在 盐酸 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以85%的产率得到N-benzyl-N-(1-hydroxy-3H-2,1-benzoxaborol-6-yl)nitrous amide
  参考文献：
  名称：

  Synthesis and evaluation of functionalized aminobenzoboroxoles as potential anti -cancer agents

  摘要：

  Several aminobenzoboroxole derivatives have been prepared starting from o-boronobenzaldehyde employing reductive amination protocol. The corresponding aminobenzoboroxole derivatives have been further functionalized as N-nitrosoaminobenzoboroxoles as well as N-benzoboroxolylureas. These derivatives have been evaluated for their anti-cancer activity on human pancreatic cancer MIAPaCa-2 and human breast cancer MDA-MB-231 cell lines. 2015 Elsevier Ltd. All rights reserved. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.06.021
• 作为产物：
  描述：

  2-(羟甲基)苯硼酸环状单酯 在 盐酸 、 sodium tetrahydroborate 、 硝酸 作用下， 以 甲醇 、 水 为溶剂， 反应 5.83h， 生成 6-(benzylamino)benzo[c][1,2]oxaborol-1(3H)-ol
  参考文献：
  名称：

  [EN] FUNCTIONALIZED AMINOBENZOBOROXOLES
  [FR] AMINOBENZOBOROXOLES FONCTIONNALISÉS

  摘要：

  揭示了功能化氨基苯硼酚类化合物，制备这些化合物的方法，以及治疗癌症的方法。

  公开号：

  WO2017031041A1

文献信息

• [EN] FUNCTIONALIZED AMINOBENZOBOROXOLES<br/>[FR] AMINOBENZOBOROXOLES FONCTIONNALISÉS
  申请人：CHANNEL THERAPEUTICS INC

  公开号：WO2017031041A1

  公开（公告）日：2017-02-23

  Disclosed are functionalized aminobenzoboroxoles compounds, method for preparing these compounds, and methods for treating cancers.

  揭示了功能化氨基苯硼酚类化合物，制备这些化合物的方法，以及治疗癌症的方法。
• Discovery of Novel Benzoxaborole-Based Potent Antitrypanosomal Agents
  作者：Dazhong Ding、Yaxue Zhao、Qingqing Meng、Dongsheng Xie、Bakela Nare、Daitao Chen、Cyrus J. Bacchi、Nigel Yarlett、Yong-Kang Zhang、Vincent Hernandez、Yi Xia、Yvonne Freund、Maha Abdulla、Kean-Hooi Ang、Joseline Ratnam、James H. McKerrow、Robert T. Jacobs、Huchen Zhou、Jacob J. Plattner

  DOI：10.1021/ml100013s

  日期：2010.7.8

  We report the discovery of benzoxaborole antitrypanosomal agents and their structure activity relationships on central linkage groups and different substitution patterns in the sulfur-linked series. The compounds showed in vitro growth inhibition IC(50) values as low as 0.02 mu g/mL and in vivo efficacy in acute murine infection models against nryapnosoma brucei.
• Synthesis and evaluation of functionalized benzoboroxoles as potential anti-tuberculosis agents
  作者：Mohammad A. Alam、Kriti Arora、Shirisha Gurrapu、Sravan K. Jonnalagadda、Grady L. Nelson、Paul Kiprof、Subash C. Jonnalagadda、Venkatram R. Mereddy

  DOI：10.1016/j.tet.2016.03.038

  日期：2016.6

  Several derivatives of aminobenzoboroxole have been prepared starting from 2-boronobenzaldehyde. All of these derivatives have been evaluated for their anti-mycobacterial activity on Mycobacterium smegmatis and cytotoxicity on breast cancer cell line MCF7. Based on these studies, all the tested molecules have been found to be generally non-toxic and benzoboroxoles with unsubstituted (primary) amines have been found to exhibit good anti-mycobacterial activity. Some of the key compounds have been evaluated for their anti-tubercular activity on Mycobacterium tuberculosis H37Rv using 7H9 and GAST media. 7-Bromo-6-aminobenzoboroxole 4 has been identified as the lead candidate compound for further development. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of functionalized aminobenzoboroxoles as potential anti -cancer agents
  作者：Pathi Suman、Bhawankumar P. Patel、Agasthya V. Kasibotla、Lucas N. Solano、Subash C. Jonnalagadda

  DOI：10.1016/j.jorganchem.2015.06.021

  日期：2015.12

  Several aminobenzoboroxole derivatives have been prepared starting from o-boronobenzaldehyde employing reductive amination protocol. The corresponding aminobenzoboroxole derivatives have been further functionalized as N-nitrosoaminobenzoboroxoles as well as N-benzoboroxolylureas. These derivatives have been evaluated for their anti-cancer activity on human pancreatic cancer MIAPaCa-2 and human breast cancer MDA-MB-231 cell lines. 2015 Elsevier Ltd. All rights reserved. (C) 2015 Elsevier B.V. All rights reserved.