3-bromopropyl 2-(1,4-dihydro-2-methyl-1,4-dioxonaphthalen-3-yloxy)acetate | 1402666-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-bromopropyl 2-(1,4-dihydro-2-methyl-1,4-dioxonaphthalen-3-yloxy)acetate
• 英文别名: 3-bromopropyl 2-((3-methyl-1, 4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)acetate；3-Bromopropyl 2-(3-methyl-1,4-dioxonaphthalen-2-yl)oxyacetate；3-bromopropyl 2-(3-methyl-1,4-dioxonaphthalen-2-yl)oxyacetate
• CAS: 1402666-17-4
• 化学式: C₁₆H₁₅BrO₅
• 分子量: 367.196
• InChiKey: IQWNFUIFPIZTEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-bromopropyl 2-(1,4-dihydro-2-methyl-1,4-dioxonaphthalen-3-yloxy)acetate 、 三苯基膦 以 异丙醇 、 甲苯 为溶剂， 以31%的产率得到3-(propyl 2-(1,4-dihydro-2-methyl-1,4-dioxonaphthalen-3-yloxy)acetate)triphenylphosphonium bromide
  参考文献：
  名称：

  1,4-Naphthoquinone Cations as Antiplasmodial Agents: Hydroxy-, Acyloxy-, and Alkoxy-Substituted Analogues

  摘要：

  Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4 49.5 nM against heteroresistant P. falciparum W2.

  DOI：

  10.1021/ml300242v
• 作为产物：
  描述：

  2-羟基-3-甲基-1,4-萘醌 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3-bromopropyl 2-(1,4-dihydro-2-methyl-1,4-dioxonaphthalen-3-yloxy)acetate
  参考文献：
  名称：

  1,4-Naphthoquinone Cations as Antiplasmodial Agents: Hydroxy-, Acyloxy-, and Alkoxy-Substituted Analogues

  摘要：

  Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4 49.5 nM against heteroresistant P. falciparum W2.

  DOI：

  10.1021/ml300242v

文献信息

• [EN] SMALL MOLECULE NAPHTHOQUINONE- AND PHTHALIMIDE-BASED LIPOCATIONS AS ANTI-PARASITIC AGENTS<br/>[FR] LIPOCATIONS À BASE DE NAPHTOQUINONE ET DE PHTALIMIDE À PETITES MOLÉCULES EN TANT QU'AGENTS ANTI-PARASITAIRES
  申请人：UNIV GEORGIA

  公开号：WO2013036766A1

  公开（公告）日：2013-03-14

  Small molecule naphthoquinone- and phthalimide-based lipocations are provided, as well as methods for their use in treating or preventing anti-parasitic diseases, such as malaria, Chagas disease, and African Sleeping Sickness.

  提供了基于小分子萘醌和邻苯二酰亚胺的脂质载体，以及它们在治疗或预防抗寄生虫疾病（如疟疾、克氏病和非洲睡眠病）中的使用方法。
• 1,4-Naphthoquinone Cations as Antiplasmodial Agents: Hydroxy-, Acyloxy-, and Alkoxy-Substituted Analogues
  作者：Xiao Lu、Ali Altharawi、Jiri Gut、Philip J. Rosenthal、Timothy E. Long

  DOI：10.1021/ml300242v

  日期：2012.12.13

  Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4 49.5 nM against heteroresistant P. falciparum W2.