2-(hydroxymethyl)-6-benzyloxyphenyl boronic acid cyclic monoester | 440105-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(hydroxymethyl)-6-benzyloxyphenyl boronic acid cyclic monoester
• 英文别名: 7-(Benzyloxy)benzo[c][1,2]oxaborol-1(3h)-ol；1-hydroxy-7-phenylmethoxy-3H-2,1-benzoxaborole
• CAS: 440105-10-2
• 化学式: C₁₄H₁₃BO₃
• 分子量: 240.066
• InChiKey: PEJPERPEBCGITJ-UHFFFAOYSA-N

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：

  2-(hydroxymethyl)-6-benzyloxyphenyl boronic acid cyclic monoester 在 palladium dihydroxide 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium chlorite 、 四(三苯基膦)钯 、 氨基磺酸 、 氢气 、 碳酸氢钠 、 sodium carbonate 、 sodium bromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 40.8h， 生成 trans-4-[4-(6-carboxy-2-hydroxyphenyl)benzoyloxy]-3-(4-hydroxybenzamido)pyrrolidine
  参考文献：
  名称：

  Synthesis and Protein Kinase Inhibitory Activity of Balanol Analogues with Modified Benzophenone Subunits

  摘要：

  A series of analogues of the protein kinase C (PKC) inhibitory natural product balanol which bear modified benzophenone subunits are described. The analogues were designed with the goal of uncovering structure - activity features that could be used in the development of PKC inhibitors with a reduced polar character compared to balanol itself. The results of these studies suggest that most of the benzophenone features found in the natural product are important for obtaining potent PKC inhibitory compounds. However, several modifications were found to lead to selective inhibitors of the related enzyme protein kinase A (PKA), and several specific modifications to the polar structural elements of the benzophenone were found to provide potent PKC inhibitors. In particular, it was found that replacement of the benzophenone carboxylate with bioisosteric equivalents could lead to potent analogues. Further, a tolerance for lipophilic substituents on the terminal benzophenone ring was uncovered. These results are discussed in light of recently available structural information for PKA.

  DOI：

  10.1021/jm020018f
• 作为产物：
  描述：

  3-苯甲氧基苯甲醇 在 正丁基锂 、 硼酸三甲酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.0h， 以64%的产率得到2-(hydroxymethyl)-6-benzyloxyphenyl boronic acid cyclic monoester
  参考文献：
  名称：

  Synthesis and Protein Kinase Inhibitory Activity of Balanol Analogues with Modified Benzophenone Subunits

  摘要：

  A series of analogues of the protein kinase C (PKC) inhibitory natural product balanol which bear modified benzophenone subunits are described. The analogues were designed with the goal of uncovering structure - activity features that could be used in the development of PKC inhibitors with a reduced polar character compared to balanol itself. The results of these studies suggest that most of the benzophenone features found in the natural product are important for obtaining potent PKC inhibitory compounds. However, several modifications were found to lead to selective inhibitors of the related enzyme protein kinase A (PKA), and several specific modifications to the polar structural elements of the benzophenone were found to provide potent PKC inhibitors. In particular, it was found that replacement of the benzophenone carboxylate with bioisosteric equivalents could lead to potent analogues. Further, a tolerance for lipophilic substituents on the terminal benzophenone ring was uncovered. These results are discussed in light of recently available structural information for PKA.

  DOI：

  10.1021/jm020018f