2-(10-bromodecyl)-3-hydroxy-1,4-naphthoquinone | 94687-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(10-bromodecyl)-3-hydroxy-1,4-naphthoquinone
• 英文别名: 2-(bromodecyl)-3-hydroxynaphthalene-1,4-dione；2-(10-bromo-decyl)-3-hydroxy-[1,4]naphthoquinone；2-(10-Brom-decyl)-3-hydroxy-[1,4]naphthochinon；3-Hydroxy-2-(10-bromo-decyl)-<1,4>naphthoquinone
• CAS: 94687-23-7
• 化学式: C₂₀H₂₅BrO₃
• 分子量: 393.321
• InChiKey: UPRKEZGTMWRUBT-UHFFFAOYSA-N

物化性质

• 熔点：
  83.7-84.5 °C
• 沸点：
  503.7±50.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(10-bromodecyl)-3-hydroxy-1,4-naphthoquinone 在 1,4-二氧六环 、 氢氧化钾 、 双氧水 、 sodium carbonate 、 苯酚 作用下， 生成 2-hydroxy-3-(9-phenoxy-nonyl)-[1,4]naphthoquinone
  参考文献：
  名称：

  Naphthoquinone Antimalarials. XXV.¹ Naphthoquinones with Oxygen in the Side Chain

  摘要：

  DOI：

  10.1021/ja01167a070
• 作为产物：
  描述：

  2-(10-bromodecyl)naphthalene-1,4-dione 在 硫酸 、 双氧水 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.17h， 生成 2-(10-bromodecyl)-3-hydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  [EN] SMALL MOLECULE NAPHTHOQUINONE- AND PHTHALIMIDE-BASED LIPOCATIONS AS ANTI-PARASITIC AGENTS
  [FR] LIPOCATIONS À BASE DE NAPHTOQUINONE ET DE PHTALIMIDE À PETITES MOLÉCULES EN TANT QU'AGENTS ANTI-PARASITAIRES

  摘要：

  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。

  公开号：

  WO2013036766A1

文献信息

• Fieser et al., Journal of the American Chemical Society, 1948, vol. 70, p. 3177
  作者：Fieser et al.

  DOI：——

  日期：——
• Design, Synthesis, and Biological Testing of Novel Naphthoquinones as Substrate-Based Inhibitors of the Quinol/Fumarate Reductase from <i>Wolinella succinogenes</i>
  作者：Hamid Reza Nasiri、M. Gregor Madej、Robin Panisch、Michael Lafontaine、Jan W. Bats、C. Roy D. Lancaster、Harald Schwalbe

  DOI：10.1021/jm400978u

  日期：2013.12.12

  Novel naphthoquinones were designed, synthesized, and tested as substrate-based inhibitors against the membrane-embedded protein quinol/fumarate reductase (QFR) from Wolinella succinogenes, a target closely related to QFRs from the human pathogens Helicobacter pylori and Campylobacter jejuni. For a better understanding of the hitherto structurally unexplored substrate binding pocket, a structure activity relationship (SAR) study was carried out. Analogues of lawsone (2-hydroxy-1,4-naphthoquinone 3a) were synthesized that vary in length and size of the alkyl side chains (3b-k). A combined study on the prototropic tautomerism of 2-hydroxy-1,4-naphthoquinones series indicated that the 1,4-tautomer is the more stable and biologically relevant isomer and that the presence of the hydroxyl group is crucial for inhibition. Furthermore, 2-bromine-1,4-naphthoquinone (4a-c) and 2-methoxy-1,4-naphthoquinone (5a-b) series were also discovered as novel and potent inhibitors. Compounds 4a and 4b showed IC50 values in low micromolar range in the primary assay and no activity in the counter DT-diaphorase assay.
• Naphthoquinone Antimalarials. XXVI.¹ Thioether Naphthoquinones²
  作者：Carl M. Moser、Marvin Paulshock

  DOI：10.1021/ja01168a015

  日期：1950.12
• 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.
• Lawsone Derivatives II.
  作者：H. MacHatzke、W.R. Vaughan

  DOI：10.1002/jps.2600530706

  日期：1964.7