3-Chloro-4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-benzonitrile | 1213786-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Chloro-4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-benzonitrile
• 英文别名: 3-chloro-4-[(1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]benzonitrile
• CAS: 1213786-76-5
• 化学式: C₁₄H₉BClNO₃
• 分子量: 285.494
• InChiKey: ULWHVOQVYWZRIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Chloro-4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-benzonitrile 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Structure–activity relationships of 6-(aminomethylphenoxy)-benzoxaborole derivatives as anti-inflammatory agent

  摘要：

  A series of novel 6-(aminomethylphenoxy)benzoxaborole analogs was synthesized for the investigation of the structure-activity relationship of the inhibition of TNF-alpha, IL-1beta, and IL-6, from lipopolysaccharide stimulated peripheral blood mononuclear cells. Compounds 9d and 9e showed potent activity against all three cytokines with IC50 values between 33 and 83 nM. Chloro substituted analog 9e (AN3485) is considered to be a promising lead for novel anti-inflammatory agent with a favorable pharmacokinetic profile. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.072
• 作为产物：
  描述：

  1,3-二氢-1-羟基-2,1-色氨酸-6-醇 、 3-氯-4-氟苯腈 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 7.0h， 以33%的产率得到3-Chloro-4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-benzonitrile
  参考文献：
  名称：

  Structure–activity relationships of 6-(aminomethylphenoxy)-benzoxaborole derivatives as anti-inflammatory agent

  摘要：

  A series of novel 6-(aminomethylphenoxy)benzoxaborole analogs was synthesized for the investigation of the structure-activity relationship of the inhibition of TNF-alpha, IL-1beta, and IL-6, from lipopolysaccharide stimulated peripheral blood mononuclear cells. Compounds 9d and 9e showed potent activity against all three cytokines with IC50 values between 33 and 83 nM. Chloro substituted analog 9e (AN3485) is considered to be a promising lead for novel anti-inflammatory agent with a favorable pharmacokinetic profile. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.072

文献信息

• BORON-CONTAINING SMALL MOLECULES
  申请人：Zhou Yasheen

  公开号：US20110166104A1

  公开（公告）日：2011-07-07

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

  该发明提供了用于治疗炎症性疾病的新型化合物，包括含有这些化合物的药物组合物，以及这些化合物与至少一个其他治疗有效剂的组合。
• Boron-containing small molecules
  申请人：Zhou Yasheen

  公开号：US08461336B2

  公开（公告）日：2013-06-11

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

  这项发明提供了多种新型化合物，可用于治疗炎症病症，包括含有这些化合物的制药组合物，以及这些化合物与至少一种额外治疗有效剂的组合。
• Structure–activity relationships of 6-(aminomethylphenoxy)-benzoxaborole derivatives as anti-inflammatory agent
  作者：Tsutomu Akama、Charlotte Virtucio、Chen Dong、Richard Kimura、Yong-Kang Zhang、James A. Nieman、Rashmi Sharma、Xiaosong Lu、Marcelo Sales、Rajeshwar Singh、Anne Wu、Xiao-Qing Fan、Liang Liu、Jacob J. Plattner、Kurt Jarnagin、Yvonne R. Freund

  DOI：10.1016/j.bmcl.2013.01.072

  日期：2013.3

  A series of novel 6-(aminomethylphenoxy)benzoxaborole analogs was synthesized for the investigation of the structure-activity relationship of the inhibition of TNF-alpha, IL-1beta, and IL-6, from lipopolysaccharide stimulated peripheral blood mononuclear cells. Compounds 9d and 9e showed potent activity against all three cytokines with IC50 values between 33 and 83 nM. Chloro substituted analog 9e (AN3485) is considered to be a promising lead for novel anti-inflammatory agent with a favorable pharmacokinetic profile. (C) 2013 Elsevier Ltd. All rights reserved.