3-(5'-bromo-2'-hydroxybenzoyl)pyridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(5'-bromo-2'-hydroxybenzoyl)pyridine
• 英文别名: (5-bromo-2-hydroxyphenyl)(pyridin-3-yl)methanone；(5-Bromo-2-hydroxyphenyl)-pyridin-3-ylmethanone；(5-bromo-2-hydroxyphenyl)-pyridin-3-ylmethanone
• 化学式: C₁₂H₈BrNO₂
• 分子量: 278.105
• InChiKey: VVAMAVOVFVKBQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5'-bromo-2'-hydroxybenzoyl)pyridine 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.75h， 以73%的产率得到3-(5'-bromo-2'-allyloxybenzoyl)pyridine
  参考文献：
  名称：

  Synthesis and evaluation of 3-salicyloylpyridine derivatives as cytotoxic mitochondrial apoptosis inducers

  摘要：

  A series of novel 3-salicyloylpyridines (4a-h) were synthesized with good yield by modified Knoevenagel-Stobbel method; o-allylation with allyl bromide lead to formation of compounds (5a-h). The synthesized compounds were characterized by spectroscopic techniques and evaluated for cytotoxic activity against human cancer cell lines. Compounds bearing hydroxyl group displayed high cytotoxicity (4a-h) as compared to o-allylated molecules (5a-h). The most active compound 4b was selected for further investigation to look for mechanism of cell death in prostate cancer (PC-3) cells. The apoptotic bodies induced by 4b in PC-3 cells were scanned by confocal microscopy and confirmed by scanning electron microscopy (SEM). Further results obtained from spectrofluorimetric determination of mitochondrial membrane potential (ΔΨm) and intracellular reactive oxygen species (ROS) in treated PC-3 cells revealed that mitochondria dependent apoptosis was involved in the cell death.

  DOI：

  10.1016/j.bmcl.2014.08.010
• 作为产物：
  描述：

  6-溴-3-甲酰色酮 在 ammonium acetate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-(5'-bromo-2'-hydroxybenzoyl)pyridine
  参考文献：
  名称：

  Synthesis and evaluation of 3-salicyloylpyridine derivatives as cytotoxic mitochondrial apoptosis inducers

  摘要：

  A series of novel 3-salicyloylpyridines (4a-h) were synthesized with good yield by modified Knoevenagel-Stobbel method; o-allylation with allyl bromide lead to formation of compounds (5a-h). The synthesized compounds were characterized by spectroscopic techniques and evaluated for cytotoxic activity against human cancer cell lines. Compounds bearing hydroxyl group displayed high cytotoxicity (4a-h) as compared to o-allylated molecules (5a-h). The most active compound 4b was selected for further investigation to look for mechanism of cell death in prostate cancer (PC-3) cells. The apoptotic bodies induced by 4b in PC-3 cells were scanned by confocal microscopy and confirmed by scanning electron microscopy (SEM). Further results obtained from spectrofluorimetric determination of mitochondrial membrane potential (ΔΨm) and intracellular reactive oxygen species (ROS) in treated PC-3 cells revealed that mitochondria dependent apoptosis was involved in the cell death.

  DOI：

  10.1016/j.bmcl.2014.08.010

文献信息

• Rhodium-Catalyzed Directing-Group-Assisted Aldehydic C-H Arylations with Aryl Halides
  作者：Maddali L. N. Rao、Boddu S. Ramakrishna

  DOI：10.1002/ejoc.201700881

  日期：2017.9.15

  A broad scope for the synthesis of 2′‐substituted benzophenones was established involving directing group (OH or NHTs) assisted C–H arylation of aryl aldehydes with aryl halides under rhodium‐catalyzed conditions.

  建立了广泛的合成2'-取代的二苯甲酮的范围，涉及在铑催化的条件下，直接基团（OH或NHTs）辅助芳基醛与芳基卤化物的C–H芳基化。
• Synthesis and evaluation of 3-salicyloylpyridine derivatives as cytotoxic mitochondrial apoptosis inducers
  作者：Alisha Sood、Vishal Sharma、Ashun Chaudhry、Rakesh Kumar、Saroj Arora、Rajnikant、Vivek Gupta、Mohan Paul S. Ishar

  DOI：10.1016/j.bmcl.2014.08.010

  日期：2014.10

  A series of novel 3-salicyloylpyridines (4a-h) were synthesized with good yield by modified Knoevenagel-Stobbel method; o-allylation with allyl bromide lead to formation of compounds (5a-h). The synthesized compounds were characterized by spectroscopic techniques and evaluated for cytotoxic activity against human cancer cell lines. Compounds bearing hydroxyl group displayed high cytotoxicity (4a-h) as compared to o-allylated molecules (5a-h). The most active compound 4b was selected for further investigation to look for mechanism of cell death in prostate cancer (PC-3) cells. The apoptotic bodies induced by 4b in PC-3 cells were scanned by confocal microscopy and confirmed by scanning electron microscopy (SEM). Further results obtained from spectrofluorimetric determination of mitochondrial membrane potential (ΔΨm) and intracellular reactive oxygen species (ROS) in treated PC-3 cells revealed that mitochondria dependent apoptosis was involved in the cell death.