5-ethoxycarbonyl-6-methyl-4-phenyl-2-[4-(7-chloroquinolin-4-ylamino)butylamino]pyrimidine | 1376766-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-ethoxycarbonyl-6-methyl-4-phenyl-2-[4-(7-chloroquinolin-4-ylamino)butylamino]pyrimidine
• 英文别名: Ethyl 2-[4-[(7-chloro-4-quinolyl)amino]butylamino]-4-methyl-6-phenyl-pyrimidine-5-carboxylate；ethyl 2-[4-[(7-chloroquinolin-4-yl)amino]butylamino]-4-methyl-6-phenylpyrimidine-5-carboxylate
• CAS: 1376766-41-4
• 化学式: C₂₇H₂₈ClN₅O₂
• 分子量: 490.005
• InChiKey: FQPUTQUMGWBCDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2-二氢-4-甲基-2-氧代-6-苯基-5-嘧啶羧酸乙酯 在 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 5-ethoxycarbonyl-6-methyl-4-phenyl-2-[4-(7-chloroquinolin-4-ylamino)butylamino]pyrimidine
  参考文献：
  名称：

  2-Aminopyrimidine based 4-aminoquinoline anti-plasmodial agents. Synthesis, biological activity, structure–activity relationship and mode of action studies

  摘要：

  2-Aminopyrimidine based 4-aminoquinolines were synthesized using an efficacious protocol. Some of the compounds showed in vitro anti-plasmodial activity against drug-sensitive CQ(S) (3D7) and drug-resistant CQ(R) (K1) strains of Plasmodium falciparum in the nM range. In particular, 5-isopropyloxycarbonyl-6-methyl-4-(2-nitrophenyl)-2-[(7-chloroquinolin-4-ylamino)butylamino] pyrimidine depicted the lowest IC50 (3.6 nM) value (56-fold less than CQ) against CQ(R) strain. Structure activity profile and binding with heme, mu-oxo-heme have been studied. Binding assays with DNA revealed better binding with target parasite type AT rich pUC18 DNA. Most compounds were somewhat cytotoxic, but especially cytostatic. Molecular docking analysis with Pf DHFR allowed identification of stabilizing interactions. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.007

文献信息

• A quinoline-based turn-off fluorescent cation sensor
  作者：Paramjit Kaur、Hardeep Kaur、Kamaljit Singh

  DOI：10.1039/c2ra22572g

  日期：——

  A quinoline-based cation sensor shows turn-off fluorescent behavior in the presence of Hg2+, Fe3+ and Cu2+ over other cations and offers discrimination of these cations from each other on the basis of the extent of quenching. The observed electronic absorption perturbations are in good agreement with theoretical (DFT, TD-DFT) calculations.

  基于喹啉的阳离子传感器在汞2+、铁3+和铜2+的存在下显示出关闭荧光的行为，而其他阳离子则没有这种行为，并且可以根据淬灭程度区分这些阳离子。观察到的电子吸收扰动与理论（DFT、TD-DFT）计算结果非常吻合。
• 2-Aminopyrimidine based 4-aminoquinoline anti-plasmodial agents. Synthesis, biological activity, structure–activity relationship and mode of action studies
  作者：Kamaljit Singh、Hardeep Kaur、Kelly Chibale、Jan Balzarini、Susan Little、Prasad V. Bharatam

  DOI：10.1016/j.ejmech.2012.03.007

  日期：2012.6

  2-Aminopyrimidine based 4-aminoquinolines were synthesized using an efficacious protocol. Some of the compounds showed in vitro anti-plasmodial activity against drug-sensitive CQ(S) (3D7) and drug-resistant CQ(R) (K1) strains of Plasmodium falciparum in the nM range. In particular, 5-isopropyloxycarbonyl-6-methyl-4-(2-nitrophenyl)-2-[(7-chloroquinolin-4-ylamino)butylamino] pyrimidine depicted the lowest IC50 (3.6 nM) value (56-fold less than CQ) against CQ(R) strain. Structure activity profile and binding with heme, mu-oxo-heme have been studied. Binding assays with DNA revealed better binding with target parasite type AT rich pUC18 DNA. Most compounds were somewhat cytotoxic, but especially cytostatic. Molecular docking analysis with Pf DHFR allowed identification of stabilizing interactions. (C) 2012 Elsevier Masson SAS. All rights reserved.