5,6-dimethoxy-4-ethyl-8-nitroquinoline | 98509-92-3

• 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: 5,6-dimethoxy-4-ethyl-8-nitroquinoline
• 英文别名: 4-Ethyl-5,6-dimethoxy-8-nitroquinoline
• CAS: 98509-92-3
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: WWKFDIZZXJHEJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-4-ethyl-8-nitroquinoline 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 4-ethyl-5-hydroxy-6-methoxy-8-nitroquinoline
  参考文献：
  名称：

  4-Substituted 5-[m-(trifluoromethyl)phenoxy]primaquine analogs as potential antimalarial agents

  摘要：

  Five 4-substituted 5-[m-(trifluoromethyl)phenoxy]primaquine analogues were synthesized and tested for radical curative activity against Plasmodium cynomolgi in Rhesus monkeys and for blood schizonticidal antimalarial activity against Plasmodium berghei in mice. In addition, they were evaluated for causal prophylactic antimalarial activity against Plasmodium berghei yoelii in mice. One compound, 4-ethyl-5-[m-(trifluoromethyl)phenoxy]primaquine (2b), showed radical curative activity equivalent to 4-methyl-5-[m-(trifluoromethyl)phenoxy]primaquine (2a). A second compound showed radical curative activity slightly less than 2a and 2b; the remaining three compounds were not active against P. cynomolgi. All five compounds showed much higher blood schizonticidal activity and less toxicity than primaquine; however, none of the compounds were as active as 2a. Three of four compounds tested showed high activity against P. berghei yoelii.

  DOI：

  10.1021/jm00149a004
• 作为产物：
  描述：

  1-氯-3-戊酮 、 2-硝基-4，5-二甲氧基苯胺 在 磷酸 作用下， 反应 2.5h， 以18%的产率得到5,6-dimethoxy-4-ethyl-8-nitroquinoline
  参考文献：
  名称：

  4-Substituted 5-[m-(trifluoromethyl)phenoxy]primaquine analogs as potential antimalarial agents

  摘要：

  Five 4-substituted 5-[m-(trifluoromethyl)phenoxy]primaquine analogues were synthesized and tested for radical curative activity against Plasmodium cynomolgi in Rhesus monkeys and for blood schizonticidal antimalarial activity against Plasmodium berghei in mice. In addition, they were evaluated for causal prophylactic antimalarial activity against Plasmodium berghei yoelii in mice. One compound, 4-ethyl-5-[m-(trifluoromethyl)phenoxy]primaquine (2b), showed radical curative activity equivalent to 4-methyl-5-[m-(trifluoromethyl)phenoxy]primaquine (2a). A second compound showed radical curative activity slightly less than 2a and 2b; the remaining three compounds were not active against P. cynomolgi. All five compounds showed much higher blood schizonticidal activity and less toxicity than primaquine; however, none of the compounds were as active as 2a. Three of four compounds tested showed high activity against P. berghei yoelii.

  DOI：

  10.1021/jm00149a004

文献信息

• Synthesis, antimalarial, antileishmanial, and antimicrobial activities of some 8-quinolinamine analogues
  作者：Meenakshi Jain、Shabana I. Khan、Babu L. Tekwani、Melissa R. Jacob、Savita Singh、Prati Pal Singh、Rahul Jain

  DOI：10.1016/j.bmc.2005.04.034

  日期：2005.7

  In the present communication, newly synthesized 8-quinolinamines (25-27) related to previously reported 2-tert-butylprimaquine (2) were evaluated for their in vitro antimalarial activity against chloroquine sensitive and resistant Plasmodium falciparum strains, in vivo antimalarial activity against P. berghei infected mice, in vitro antileishmanial activity against Leishmania donovani, in vitro antimicrobial activity against various fungi and bacteria, and cytotoxicity in a panel of mammalian cell lines. No promising cytotoxicities were observed for compounds reported herein. Analogue 25 was found to exhibit curative antimalarial activity at a dose of 25 mg/kg/day x 4 in a P. berghei infected mice model, and produced suppressive activity at a lower dose of 10 mg/kg/ day x 4. In vitro antileishmanial activities (IC50 and IC90) comparable to standard drug pentamidine were exhibited by all synthesized 8-quinolinamines 25-27. At the same time, promising antibacterial and antifungal activities were also observed for synthesized compounds against a panel consisting of several bacteria and fungi. (c) 2005 Elsevier Ltd. All rights reserved.
• CARROLL, F. I.;BERRANG, B.;LINN, C. P., J. MED. CHEM., 1985, 28, N 11, 1564-1657
  作者：CARROLL, F. I.、BERRANG, B.、LINN, C. P.

  DOI：——

  日期：——
• 4-Substituted 5-[m-(trifluoromethyl)phenoxy]primaquine analogs as potential antimalarial agents
  作者：F. Ivy Carroll、Bertold Berrang、C. P. Linn

  DOI：10.1021/jm00149a004

  日期：1985.11

  Five 4-substituted 5-[m-(trifluoromethyl)phenoxy]primaquine analogues were synthesized and tested for radical curative activity against Plasmodium cynomolgi in Rhesus monkeys and for blood schizonticidal antimalarial activity against Plasmodium berghei in mice. In addition, they were evaluated for causal prophylactic antimalarial activity against Plasmodium berghei yoelii in mice. One compound, 4-ethyl-5-[m-(trifluoromethyl)phenoxy]primaquine (2b), showed radical curative activity equivalent to 4-methyl-5-[m-(trifluoromethyl)phenoxy]primaquine (2a). A second compound showed radical curative activity slightly less than 2a and 2b; the remaining three compounds were not active against P. cynomolgi. All five compounds showed much higher blood schizonticidal activity and less toxicity than primaquine; however, none of the compounds were as active as 2a. Three of four compounds tested showed high activity against P. berghei yoelii.