3-(2,2-dimethylpropyl)-4-hydroxynaphthalene-1,2-dione | 180918-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(2,2-dimethylpropyl)-4-hydroxynaphthalene-1,2-dione
• 英文别名: 2-hydroxy-3-neopentyl-1,4-naphthoquinone；2-hydroxy-3-neopentyl-[1,4]naphthoquinone；2-Hydroxy-3-neopentyl-[1,4]naphthochinon；2-(2.2-dimethylpropyl)-3-hydroxy-naphthalene-1 4-dione；2-(2.2-dimethylpropyl)-3-hydroxy-naphthalene-1,4-dione
• CAS: 180918-46-1
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: CYGFOOBBDNUOKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  376.5±42.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  对硝基甲苯 、 3-(2,2-dimethylpropyl)-4-hydroxynaphthalene-1,2-dione 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Neopentyl-1,4-naphthoquinone 在 双氧水 、 sodium carbonate 、 硫酸 作用下， 生成 3-(2,2-dimethylpropyl)-4-hydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  Design, Synthesis, and Biological Testing of Novel Naphthoquinones as Substrate-Based Inhibitors of the Quinol/Fumarate Reductase from Wolinella succinogenes

  摘要：

  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.

  DOI：

  10.1021/jm400978u

文献信息

• Pesticidal compounds
  申请人：BTG International Limited

  公开号：US05962002A1

  公开（公告）日：1999-10-05

  This invention relates to 1,1,1,4-substituted naphthaline compounds, compositions, processes for their preparation and processes for their use as pesticides, especially insecticides, acaricides and fungicides.

  本发明涉及1,1,1,4-取代萘化合物、组成物、其制备方法和作为杀虫剂、杀螨剂和杀真菌剂的用途的方法。
• PESTICIDAL COMPOUNDS
  申请人：BTG INTERNATIONAL LIMITED

  公开号：EP0802730B1

  公开（公告）日：1999-06-23
• US5962002A
  申请人：——

  公开号：US5962002A

  公开（公告）日：1999-10-05
• 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.