isopropyl 2-chloro-4-methyl-6-(2-nitrophenyl)pyrimidine-5-carboxylate | 1376766-59-4

• 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: isopropyl 2-chloro-4-methyl-6-(2-nitrophenyl)pyrimidine-5-carboxylate
• CAS: 1376766-59-4
• 化学式: C₁₅H₁₄ClN₃O₄
• 分子量: 335.747
• InChiKey: DOGDBMNFANENTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  isopropyl 2-chloro-4-methyl-6-(2-nitrophenyl)pyrimidine-5-carboxylate 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 生成 isopropyl 2-[(1-(2-(7-chloroquinolin-4-ylamino)ethyl)-1H-1,2,3-triazol-4-yl)methoxy]-4-methyl-6-(2-nitrophenyl)pyrimidine-5-carboxylate
  参考文献：
  名称：

  嘧啶-氯喹啉杂化物：合成和抗血浆活性

  摘要：

  合成了三唑系留的7-氯喹啉-嘧啶-5-羧酸酯杂化物，并评估了其对恶性疟原虫的氯喹敏感（CQ S）NF54菌株的抗疟原虫活性。该系列中最活跃的杂种进一步针对寄生虫的氯喹抗性（CQ R）Dd2菌株进行了筛选，并针对哺乳动物的Vero细胞系进行了体外细胞毒性研究。此外，它们的理化特性，与血红素（单体和μ-氧代二聚体）和DNA [pUC-18，小牛胸腺（CT）]的结合研究使我们提出了本系列中最活跃成员的合理结合方式。

  DOI：

  10.1016/j.ejmech.2018.02.021
• 作为产物：
  描述：

  Propan-2-yl 6-methyl-4-(2-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 硝酸 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 0.75h， 生成 isopropyl 2-chloro-4-methyl-6-(2-nitrophenyl)pyrimidine-5-carboxylate
  参考文献：
  名称：

  Primaquine–pyrimidine hybrids: Synthesis and dual-stage antiplasmodial activity

  摘要：

  A series of novel pyrimidine primaquine hybrids were synthesized and their effectiveness against the blood and liver stages of malaria parasites was evaluated. The hybrids displayed enhanced liver stage in vitro activity against P. berghei liver stage infection. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.045

文献信息

• Ferrocene-pyrimidine conjugates: Synthesis, electrochemistry, physicochemical properties and antiplasmodial activities
  作者：Rakesh Chopra、Carmen de Kock、Peter Smith、Kelly Chibale、Kamaljit Singh

  DOI：10.1016/j.ejmech.2015.05.043

  日期：2015.7

  The promise of hybrid antimalarial agents and the precedence set by the antimalarial drug ferroquine prompted us to design ferrocene-pyrimidine conjugates. Herein, we report the synthesis, electrochemistry and anti-plasmodial evaluation of ferrocenyl-pyrimidine conjugates against chloroquine susceptible NF54 strain of the malaria parasite Plasmodium falciparum. Also their physicochemical properties have been studied. (C) 2015 Elsevier Masson SAS. All rights reserved.
• 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.