2-selenobenzo[h]quinoline-3-carbaldehyde | 1146978-28-0

• 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-selenobenzo[h]quinoline-3-carbaldehyde
• 英文别名: 2-seleno-3-formylbenzo[h]quinoline
• CAS: 1146978-28-0
• 化学式: C₁₄H₉NOSe
• 分子量: 286.192
• InChiKey: VQZKOHLTUKUWGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-selenobenzo[h]quinoline-3-carbaldehyde 、 乙二醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以60%的产率得到3-(1,3-dioxolan-2-yl)benzo[h]quinoline-2-selenol
  参考文献：
  名称：

  An Efficient, Microwave-Assisted, One-Pot Synthesis of Dioxolano Quinoline/benzo[h]quinolines as Potent Antibacterial Agents

  摘要：

  Quinolines/benzo[h]quinolines are associated with a broad spectrum of biological activities. In view of this, 3-(1,3-dioxolan-2-yl)quinoline/benzo[h]quinoline-2-thiol/selenols were prepared under microwave irradiation through one-pot reactions, and these quinolines/ benzo[h]quinolines were evaluated for potential antibacterial activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  DOI：

  10.1080/10426500902797095
• 作为产物：
  描述：

  2-chlorobenzo[h]quinoline-3-carbaldehyde 在 sodium hydrogen selenide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以63%的产率得到2-selenobenzo[h]quinoline-3-carbaldehyde
  参考文献：
  名称：

  Synthesis of novel benzo[h]quinolines: Wound healing, antibacterial, DNA binding and in vitro antioxidant activity

  摘要：

  We have characterized a new class of 2-mercapto/2-selenobenzo[h]quinoline-3-carbaldehyde (3/4). Antibacterial potential of these compounds against a wide range of Gram-positive and Gram-negative bacteria was studied. The selenium containing compound 4 showed significant inhibition zone on Staphylococcus aureus (22.76 +/- 0.14), Bacillus subtilis (20.63 +/- 0.24), and Streptococcus pyogenes (19.54 +/- 0.20) over sulfur containing compound 3. To validate the ethnotherapeutic claims of the synthetic compounds in skin diseases, wound healing activity was studied, besides antioxidant activity to understand the mechanism of wound healing. The interaction behavior of these compounds with DNA was investigated by absorption spectra (obtained K-b constant for 3 is 2.7 x 10(5) and for 4 is 3.8 x 10(6)), viscosity, and thermal denaturation studies. Finally, the results show that the DNA intercalated 314 compounds are strong antioxidants; they show significan wound healing activity and protect oxidative DNA damage from harmful free radical reactions. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.07.006

文献信息

• An Efficient, Microwave-Assisted, One-Pot Synthesis of Dioxolano Quinoline/benzo[<i>h</i>]quinolines as Potent Antibacterial Agents
  作者：H. R. Prakash Naik、H. S. Bhojya Naik、T. R. Ravikumar Naik、D. S. Lamani、T. Aravinda

  DOI：10.1080/10426500902797095

  日期：2010.1.29

  Quinolines/benzo[h]quinolines are associated with a broad spectrum of biological activities. In view of this, 3-(1,3-dioxolan-2-yl)quinoline/benzo[h]quinoline-2-thiol/selenols were prepared under microwave irradiation through one-pot reactions, and these quinolines/ benzo[h]quinolines were evaluated for potential antibacterial activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
• Synthesis of novel benzo[h]quinolines: Wound healing, antibacterial, DNA binding and in vitro antioxidant activity
  作者：Halehatty R. Prakash Naik、Halehatty S. Bhojya Naik、Thangali R. Ravikumar Naik、H. Raja Naika、K. Gouthamchandra、Riaz Mahmood、B.M. Khadeer Ahamed

  DOI：10.1016/j.ejmech.2008.07.006

  日期：2009.3

  We have characterized a new class of 2-mercapto/2-selenobenzo[h]quinoline-3-carbaldehyde (3/4). Antibacterial potential of these compounds against a wide range of Gram-positive and Gram-negative bacteria was studied. The selenium containing compound 4 showed significant inhibition zone on Staphylococcus aureus (22.76 +/- 0.14), Bacillus subtilis (20.63 +/- 0.24), and Streptococcus pyogenes (19.54 +/- 0.20) over sulfur containing compound 3. To validate the ethnotherapeutic claims of the synthetic compounds in skin diseases, wound healing activity was studied, besides antioxidant activity to understand the mechanism of wound healing. The interaction behavior of these compounds with DNA was investigated by absorption spectra (obtained K-b constant for 3 is 2.7 x 10(5) and for 4 is 3.8 x 10(6)), viscosity, and thermal denaturation studies. Finally, the results show that the DNA intercalated 314 compounds are strong antioxidants; they show significan wound healing activity and protect oxidative DNA damage from harmful free radical reactions. (C) 2008 Elsevier Masson SAS. All rights reserved.