6-bromomethyl-2-phenylquinoline-4-carboxylic acid ethyl ester | 850010-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-bromomethyl-2-phenylquinoline-4-carboxylic acid ethyl ester
• 英文别名: ethyl 6-(bromomethyl)-2-phenylquinoline-4-carboxylate
• CAS: 850010-57-0
• 化学式: C₁₉H₁₆BrNO₂
• 分子量: 370.246
• InChiKey: QUBWZAUFJPNFFR-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C(Solv: ethanol (64-17-5))
• 沸点：
  504.4±50.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-bromomethyl-2-phenylquinoline-4-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 26.0h， 生成 sodium 2-phenyl-6-pyrazol-1-ylmethylquinoline-4-carboxylate
  参考文献：
  名称：

  Synthesis of brequinar analogue inhibitors of malaria parasite dihydroorotate dehydrogenase

  摘要：

  A series of 2-phenyl quinoline-4-carboxylic acid derivatives related to brequinar, an inhibitor of human dihydroorotate dehydrogenase (DHODH), has been prepared and evaluated as inhibitors of DHODH from the malaria parasite Plasmodium falciparum. Brequinar was essentially inactive against PfDHODH (IC50 880 mu M) whereas several members of the series inhibited PfDHODH. Unexpectedly, replacement of the carboxylic acid required for brequinar to inhibit hDHODH was not essential in the diisopropylamides that inhibited PfDHODH. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.017
• 作为产物：
  描述：

  6-甲基-2-苯基喹啉-4-羧酸 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 10.0h， 生成 6-bromomethyl-2-phenylquinoline-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of brequinar analogue inhibitors of malaria parasite dihydroorotate dehydrogenase

  摘要：

  A series of 2-phenyl quinoline-4-carboxylic acid derivatives related to brequinar, an inhibitor of human dihydroorotate dehydrogenase (DHODH), has been prepared and evaluated as inhibitors of DHODH from the malaria parasite Plasmodium falciparum. Brequinar was essentially inactive against PfDHODH (IC50 880 mu M) whereas several members of the series inhibited PfDHODH. Unexpectedly, replacement of the carboxylic acid required for brequinar to inhibit hDHODH was not essential in the diisopropylamides that inhibited PfDHODH. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.017