3-oxiranyl-2-phenylquinoline-4-carboxylic acid diisopropylamide | 650607-41-3

• 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: 3-oxiranyl-2-phenylquinoline-4-carboxylic acid diisopropylamide
• 英文别名: 3-(Oxiran-2-yl)-2-phenyl-N,N-di(propan-2-yl)quinoline-4-carboxamide；3-(oxiran-2-yl)-2-phenyl-N,N-di(propan-2-yl)quinoline-4-carboxamide
• CAS: 650607-41-3
• 化学式: C₂₄H₂₆N₂O₂
• 分子量: 374.483
• InChiKey: ZSAFOIKNMPJBNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  lithium pyrrolidide 、 3-oxiranyl-2-phenylquinoline-4-carboxylic acid diisopropylamide 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-(2-hydroxy-1-pyrrolidin-1-ylethyl)-2-phenylquinoline-4-carboxylic acid diisopropylamide
  参考文献：
  名称：

  Ring opening reactions of quinoline substituted epoxides

  摘要：

  6-Oxiranyl- and 3-oxiranyl-2-phenylquinoline-4-carboxylic acid diisopropylamides react with secondary amines and lithium amides to give (aminohydroxyethyl)quinolines but with opposite regioselectivities. Upon epoxidation of 3-formylquinoline 2 a similar to5:1 mixture of atropisomers is formed. This ratio is maintained upon epoxide ring-opening with amines in ethanol at reflux, but with lithium amides at room temperature a 1.3:1 ratio of isomers is obtained. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.062
• 作为产物：
  描述：

  3-甲基-2-苯基-4-喹啉羧酸 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 2-硝基丙烷 、 potassium tert-butylate 、 sodium 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 42.33h， 生成 3-oxiranyl-2-phenylquinoline-4-carboxylic acid diisopropylamide
  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

文献信息

• Synthesis of brequinar analogue inhibitors of malaria parasite dihydroorotate dehydrogenase
  作者：Andrew N. Boa、Shane P. Canavan、Paul R. Hirst、Christopher Ramsey、Andrew M.W. Stead、Glenn A. McConkey

  DOI：10.1016/j.bmc.2005.01.017

  日期：2005.3

  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.
• Ring opening reactions of quinoline substituted epoxides
  作者：Andrew N. Boa、Stephen Clark、Paul R. Hirst、Robert Westwood

  DOI：10.1016/j.tetlet.2003.10.062

  日期：2003.12

  6-Oxiranyl- and 3-oxiranyl-2-phenylquinoline-4-carboxylic acid diisopropylamides react with secondary amines and lithium amides to give (aminohydroxyethyl)quinolines but with opposite regioselectivities. Upon epoxidation of 3-formylquinoline 2 a similar to5:1 mixture of atropisomers is formed. This ratio is maintained upon epoxide ring-opening with amines in ethanol at reflux, but with lithium amides at room temperature a 1.3:1 ratio of isomers is obtained. (C) 2003 Elsevier Ltd. All rights reserved.