1-{4-[2-Nitro-4-(trifluoromethyl)phenoxy]phenyl}ethan-1-one | 903288-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-{4-[2-Nitro-4-(trifluoromethyl)phenoxy]phenyl}ethan-1-one
• 英文别名: 1-[4-[2-nitro-4-(trifluoromethyl)phenoxy]phenyl]ethanone
• CAS: 903288-98-2
• 化学式: C₁₅H₁₀F₃NO₄
• 分子量: 325.244
• InChiKey: VBLACFVBSWNRSL-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  384.5±42.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-{4-[2-Nitro-4-(trifluoromethyl)phenoxy]phenyl}ethan-1-one 、 1-(4-甲醛基苯基)咪唑 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以71%的产率得到(E)-3-(4-(1H-imidazol-1-yl)phenyl)-1-(4-(2-nitro-4-(trifluoromethyl)phenoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Novel aryloxy azolyl chalcones with potent activity against Mycobacterium tuberculosis H37Rv

  摘要：

  A series of twenty seven novel aryloxy azolyl chalcones were synthesized and evaluated in vitro for the growth inhibition of Mycobacterium tuberculosis H37Rv. Ten compounds from this series exhibited good activity with MIC in the range of 3.12-0.78 mu g/mL and six of them were found non-toxic against VERO cells and MBMDMos (mouse bone-marrow derived macrophages), were further evaluated ex-vivo for their potential to kill intracellular bacilli. Two compounds 4 and 19 showed 99% and 71% killing respectively, of intracellular bacilli in MBMDMos infection model. Further, compound 19, an imidazolyl chalcone with a 2,4-difluorobenzyloxy moiety also exhibited moderate in vivo activity in mice against virulent M. tuberculosis, thus providing a new structural lead towards TB drug development. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.037
• 作为产物：
  描述：

  4-氯-3-硝基三氟甲苯 、 对羟基苯乙酮 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.67h， 以73%的产率得到1-{4-[2-Nitro-4-(trifluoromethyl)phenoxy]phenyl}ethan-1-one
  参考文献：
  名称：

  Novel aryloxy azolyl chalcones with potent activity against Mycobacterium tuberculosis H37Rv

  摘要：

  A series of twenty seven novel aryloxy azolyl chalcones were synthesized and evaluated in vitro for the growth inhibition of Mycobacterium tuberculosis H37Rv. Ten compounds from this series exhibited good activity with MIC in the range of 3.12-0.78 mu g/mL and six of them were found non-toxic against VERO cells and MBMDMos (mouse bone-marrow derived macrophages), were further evaluated ex-vivo for their potential to kill intracellular bacilli. Two compounds 4 and 19 showed 99% and 71% killing respectively, of intracellular bacilli in MBMDMos infection model. Further, compound 19, an imidazolyl chalcone with a 2,4-difluorobenzyloxy moiety also exhibited moderate in vivo activity in mice against virulent M. tuberculosis, thus providing a new structural lead towards TB drug development. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.037

文献信息

• Novel aryloxy azolyl chalcones with potent activity against Mycobacterium tuberculosis H37Rv
  作者：Vijay K. Marrapu、Vinita Chaturvedi、Shubhra Singh、Shyam Singh、Sudhir Sinha、Kalpana Bhandari

  DOI：10.1016/j.ejmech.2011.06.037

  日期：2011.9

  A series of twenty seven novel aryloxy azolyl chalcones were synthesized and evaluated in vitro for the growth inhibition of Mycobacterium tuberculosis H37Rv. Ten compounds from this series exhibited good activity with MIC in the range of 3.12-0.78 mu g/mL and six of them were found non-toxic against VERO cells and MBMDMos (mouse bone-marrow derived macrophages), were further evaluated ex-vivo for their potential to kill intracellular bacilli. Two compounds 4 and 19 showed 99% and 71% killing respectively, of intracellular bacilli in MBMDMos infection model. Further, compound 19, an imidazolyl chalcone with a 2,4-difluorobenzyloxy moiety also exhibited moderate in vivo activity in mice against virulent M. tuberculosis, thus providing a new structural lead towards TB drug development. (C) 2011 Elsevier Masson SAS. All rights reserved.