2-tert-butyl-5,6-dimethoxy-4-methyl-8-nitroquinoline | 762301-46-2

• 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: 2-tert-butyl-5,6-dimethoxy-4-methyl-8-nitroquinoline
• 英文别名: 2-tert-butyl-4-methyl-5,6-dimethoxy-8-nitroquinoline
• CAS: 762301-46-2
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: BCVIEQVOFQYJCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  435.3±40.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  2-tert-butyl-5,6-dimethoxy-4-methyl-8-nitroquinoline 在 盐酸 、 氢氧化钾 、 三氯氧磷 作用下， 反应 16.0h， 生成 2-tert-butyl-6-methoxy-4-methyl-8-nitro-5-(3-trifluoromethylphenoxy)quinoline
  参考文献：
  名称：

  Synthesis, antimalarial, antileishmanial, and antimicrobial activities of some 8-quinolinamine analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.04.034
• 作为产物：
  描述：

  4-甲基-5,6-二甲氧基-8-硝基喹啉 、 三甲基乙酸 在 硫酸 ammonium persulfate 、 silver nitrate 、 三甲基乙酸 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以47%的产率得到2-tert-butyl-5,6-dimethoxy-4-methyl-8-nitroquinoline
  参考文献：
  名称：

  Synthesis, antimalarial, antileishmanial, and antimicrobial activities of some 8-quinolinamine analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.04.034

文献信息

• Process for preparation of ring-substituted 8-aminoquinoline analogs as antimalarial agents
  申请人：——

  公开号：US20040192724A1

  公开（公告）日：2004-09-30

  The present invention is concerned with the development of novel 8-aminoquinoline analogs in the treatment and prevention of malaria and the said compound has broad spectrum of activity against the blood as well as tissue stages of the human malaria parasites makes these compounds very attractive in the cure and prevention of malaria caused by drug-sensitive and multidrug resistant strains and also it is expected that development of these compounds as ideal antimalarial agents may lead to suppression as well as radical cure of the malaria infection with single drug therapy.

  本发明涉及新型8-氨基喹啉类似物在治疗和预防疟疾方面的开发，所述化合物对人类疟原虫的血期及组织期具有广谱活性，使得这些化合物在治疗和预防由药物敏感和多药耐药菌株引起的疟疾方面极具吸引力。同时，预期将这些化合物开发为理想的抗疟药物可能会导致单一药物疗法既能抑制又能根治疟疾感染。
• RING-SUBSTITUTED 8-AMINOQUINOLINE DERIVATIVES AS ANTIMALARIAL AGENTS
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：EP1606263A1

  公开（公告）日：2005-12-21
• Methods and compositions for the treatment of neurodegenerative disorders
  申请人：Jin Xiaowei

  公开号：US20080044390A1

  公开（公告）日：2008-02-21

  The present invention features compositions, kits, and methods for treating, preventing, and ameliorating neurodegenerative disorders, e.g., Huntington's disease.
• US6979740B2
  申请人：——

  公开号：US6979740B2

  公开（公告）日：2005-12-27
• [EN] RING-SUBSTITUTED 8-AMINOQUNOLINE DERIVATES AS ANTIMALARIAL AGENTS<br/>[FR] DERIVES DE 8-AMINOQUINOLINE A CYCLE SUBSTITUE UTILES COMME AGENTS ANTI-PALUDEENS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2004085402A1

  公开（公告）日：2004-10-07

  The present invention is concerned with the development of novel 8-aminoquinoline analogs according to formula (1) with the definitions of R, R<1>, R<2> and R<3> in the description in the treatment and prevention of malaria. The said compounds have broad, spectrum of activity against the blood as well as tissue stages of the human malaria parasites makes these compounds very attractive in the cure and prevention of malaria caused by drug-sensitive and multidrug resistant strains. It is expected that development of these compounds as ideal antimalarial agents may lead to suppression as well as radical cure of the malaria infection with single drug therapy.