4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)oxy)benzoic acid | 1196473-45-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)oxy)benzoic acid
• 英文别名: 4-(1-Hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)benzoic acid；4-[(1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]benzoic acid
• CAS: 1196473-45-6
• 化学式: C₁₄H₁₁BO₅
• 分子量: 270.049
• InChiKey: UVIWTXKCGYBIJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)oxy)benzoic acid 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到[4-[(1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]phenyl]methanol
  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：

  2-溴-4-氟苯甲醛 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium tetrahydroborate 、 potassium acetate 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)oxy)benzoic acid
  参考文献：
  名称：

  Synthesis and SAR of novel benzoxaboroles as a new class of β-lactamase inhibitors

  摘要：

  A new class of benzoxaborole beta-lactamase inhibitors were designed and synthesized. 6-Aryloxy benzoxaborole 22 inhibited AmpC P99 and CMY-2 with K-i values in the low nanomolar range. Compound 22 restored antibacterial activity of ceftazidime against Enterobacter cloacae P99 expressing AmpC, a class C beta-lactamase enzyme. The SAR around the arylbenzoxaboroles, which included the influence of linker and substitutions was also established. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.024

文献信息

• Transition-metal-free, one-pot synthesis of benzoxaboroles from <i>o</i>-bromobenzaldehydes <i>via</i> visible-light-promoted borylation
  作者：Jinghan Luo、Xingxing Jia、Yanjun Hu、Jianchao Chen、Tiemin Sun

  DOI：10.1039/d1ob01853a

  日期：——

  A novel and simple one-pot stepwise method to synthesize benzoxaboroles was demonstrated. This step-by-step synthetic method includes photocatalytic boronization with phenothiazine as a photocatalyst and sequential water-induced reduction in the presence of bis(pinacolato)diboron. A series of o-bromobenzaldehydes were well-tolerated under the standard conditions. In addition, this method has been successfully

  展示了一种新颖且简单的一锅法逐步合成苯并恶硼烷的方法。这种分步合成方法包括使用吩噻嗪作为光催化剂的光催化硼化和在双（频哪醇）二硼存在下的连续水诱导还原。一系列邻溴苯甲醛在标准条件下具有良好的耐受性。此外，该方法已成功应用于抗结核候选药物GSK 3036656和抗真菌药物tavaborole的合成。
• Synthesis and SAR of novel benzoxaboroles as a new class of β-lactamase inhibitors
  作者：Yi Xia、Kathy Cao、Yasheen Zhou、M.R.K. Alley、Fernando Rock、Manisha Mohan、Maliwan Meewan、Stephen J. Baker、Sarah Lux、Charles Z. Ding、Guofeng Jia、Maureen Kully、Jacob J. Plattner

  DOI：10.1016/j.bmcl.2011.02.024

  日期：2011.4

  A new class of benzoxaborole beta-lactamase inhibitors were designed and synthesized. 6-Aryloxy benzoxaborole 22 inhibited AmpC P99 and CMY-2 with K-i values in the low nanomolar range. Compound 22 restored antibacterial activity of ceftazidime against Enterobacter cloacae P99 expressing AmpC, a class C beta-lactamase enzyme. The SAR around the arylbenzoxaboroles, which included the influence of linker and substitutions was also established. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.