3-methyl-4-(pyridin-3-yl)phenylboronic acid | 1359945-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-methyl-4-(pyridin-3-yl)phenylboronic acid
• 英文别名: (3-Methyl-4-pyridin-3-ylphenyl)boronic acid
• CAS: 1359945-09-7
• 化学式: C₁₂H₁₂BNO₂
• 分子量: 213.044
• InChiKey: BNMBRDBVDKLPNY-UHFFFAOYSA-N

物化性质

• 熔点：
  211 °C
• 沸点：
  405.0±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-4-(pyridin-3-yl)phenylboronic acid 、 5-bromo-2-(pyridin-3-yl)benzaldehyde 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 20.0h， 以97%的产率得到2-(pyridin-3-yl)-5-(3-methyl-4-pyridin-3-ylphenyl)benzaldehyde
  参考文献：
  名称：

  First Evidence That Oligopyridines, α-Helix Foldamers, Inhibit Mcl-1 and Sensitize Ovarian Carcinoma Cells to Bcl-x_L-Targeting Strategies

  摘要：

  Apoptosis control defects such as the deregulation of Bcl-2 family member expression are frequently involved in chemoresistance. In ovarian carcinoma, we previously demonstrated that Bcl-xL and Mcl-1 cooperate to protect cancer cells against apoptosis and their concomitant inhibition leads to massive apoptosis even in the absence of chemotherapy. Whereas Bcl-xL inhibitors are now available, Mcl-1 inhibition, required to sensitize cells to Bcl-xL-targeting strategies, remains problematic. In this context, we designed and synthesized oligopyridines potentially targeting the Mcl-1 hydrophobic pocket, evaluated their capacity to inhibit Mcl-1 in live cells, and implemented a functional screening assay to evaluate their ability to sensitize ovarian carcinoma cells to Bcl-xL-targeting strategies. We established structureactivity relationships and focused our attention on MR29072, named Pyridoclax. Surface plasmon resonance assay demonstrated that pyridoclax directly binds to Mcl-1. Without cytotoxic activity when administered as a single agent, pyridoclax induced apoptosis in combination with Bcl-xL-targeting siRNA or with ABT-737 in ovarian, lung, and mesothelioma cancer cells.

  DOI：

  10.1021/jm500672y
• 作为产物：
  描述：

  2-溴吡啶-5-硼酸 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 27.5h， 生成 3-methyl-4-(pyridin-3-yl)phenylboronic acid
  参考文献：
  名称：

  Synthesis of new linear poly(phenylpyridyl) chains

  摘要：

  This paper describes for the first time an efficient approach of Suzuki Miyaura cross-coupling reaction leading to new mixed linear unsymmetric phenylpyridyl chains (garlands). We have studied the synthesis of new phenylpyridyl boronic species and their reactivity with a dihalogenated bipyridine to obtain four and six unit phenylpyridines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.074