2-but-2-enyloxy-[1,4]naphthoquinone | 52422-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-but-2-enyloxy-[1,4]naphthoquinone
• 英文别名: 2-But-2-enyloxy-[1,4]naphthochinon；γ-Methylallyloxy-2 naphthochinon-1.4；2-(2-Butenyloxy)-1,4-naphthochinon
• CAS: 52422-56-7
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: ULSQVFDLZFKWAF-NSCUHMNNSA-N

物化性质

• 熔点：
  137 °C
• 沸点：
  384.3±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-but-2-enyloxy-[1,4]naphthoquinone 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  THE ALKYLATION OF HYDROXYNAPHTHOQUINONE. III. A SYNTHESIS OF LAPACHOL

  摘要：

  DOI：

  10.1021/ja01402a030
• 作为产物：
  描述：

  1-溴-2-丁烯 、 2-hydroxy-1,4-naphthoquinone silver salt 在 乙醚 作用下， 生成 2-but-2-enyloxy-[1,4]naphthoquinone
  参考文献：
  名称：

  THE ALKYLATION OF HYDROXYNAPHTHOQUINONE. III. A SYNTHESIS OF LAPACHOL

  摘要：

  DOI：

  10.1021/ja01402a030

文献信息

• Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1)
  作者：Jinlei Bian、Lili Xu、Bang Deng、Xue Qian、Jun Fan、Xiuwen Yang、Fang Liu、Xiaoli Xu、Xiaoke Guo、Xiang Li、Haopeng Sun、Qidong You、Xiaojin Zhang

  DOI：10.1016/j.bmcl.2015.01.057

  日期：2015.3

  Natural product (+/-)-dunnione (2) and its ortho-quinone analogues (3-8) were synthesized and found to be substrates for NQO1. The structure-activity relationship study revealed that the biological activity was favored by the presence of methyl group at the C ring and methoxy group at the A ring. The docking studies supported the rationalization of the metabolic studies. Deeper location in the active site of NQO1, interactions with hydrophobic pocket and C-H center dot center dot center dot pi interactions with the adjacent Phe178 residue contributed to the better catalytic efficiency and specificity to NQO1. Cytotoxicity studies and determination of superoxide (O-2(center dot)) production in the presence and absence of the NOQ1 inhibitor dicoumarol confirmed that the ortho-quinones exerted their antitumor activity through NQO1-mediated ROS production by redox cycling. (C) 2015 Elsevier Ltd. All rights reserved.