1-(2-fluorophenyl)-3-(4-carboxyphenyl)triazene | 1338224-91-1

• 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-(2-fluorophenyl)-3-(4-carboxyphenyl)triazene
• 英文别名: 4-[2-(2-Fluorophenyl)iminohydrazinyl]benzoic acid
• CAS: 1338224-91-1
• 化学式: C₁₃H₁₀FN₃O₂
• 分子量: 259.24
• InChiKey: VHATVOJKIMAMLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氟苯胺 、 对氨基苯甲酸 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 以64%的产率得到1-(2-fluorophenyl)-3-(4-carboxyphenyl)triazene
  参考文献：
  名称：

  In vitro evaluation of triazenes: DNA cleavage, antibacterial activity and cytotoxicity against acute myeloid leukemia cells

  摘要：

  The asymmetric diazoamines 1-(2-chlorophenyl)-3-(4-carboxyphenyl) triazene (1), 1-(2-fluorophenyl)-3-(4-carboxyphenyl) triazene (2) and 1-(2-fluorophenyl)-3-(4-amidophenyl) triazene (3) were evaluated for their ability to cleave pUC18 and pBSKII plasmid DNA, antibacterial activity and in vitro cytotoxicity against acute myeloid leukemia cells and normal leukocytes using the bioassay of reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). The triazenes showed ability to cleave the two types of plasmid DNA: triazene 1 at pH 8.0 and 50 degrees C; triazene 2 at pH 6.5 and 37 and 50 degrees C; triazene 3 at pH 6.5 and 37 degrees C. The compounds presented cytotoxic activity against myeloid leukemia cells. Compound 1 showed high activity against B. cereus (MIC = 32 mu g mL(-1)). The observation of intermolecular hydrogen bonding in the solid state of compound 3, based on the structural analysis by X-ray crystallography, as well as the results of IR and UV-Vis spectroscopic analyses of compounds 1, 2 and 3 are discussed in the present work.

  DOI：

  10.1590/s0103-50532010001200009

文献信息

• In vitro evaluation of triazenes: DNA cleavage, antibacterial activity and cytotoxicity against acute myeloid leukemia cells
  作者：Vanessa O. Domingues、Rosmari Hörner、Luiz G. B. Reetz、Fábio Kuhn、Virgínia M. Coser、Jacqueline N. Rodrigues、Rita Bauchspiess、Waldir V. Pereira、Gustavo L. Paraginski、Aline Locatelli、Juliana de O. Fank、Vinícius F. Giglio、Manfredo Hörner

  DOI：10.1590/s0103-50532010001200009

  日期：——

  The asymmetric diazoamines 1-(2-chlorophenyl)-3-(4-carboxyphenyl) triazene (1), 1-(2-fluorophenyl)-3-(4-carboxyphenyl) triazene (2) and 1-(2-fluorophenyl)-3-(4-amidophenyl) triazene (3) were evaluated for their ability to cleave pUC18 and pBSKII plasmid DNA, antibacterial activity and in vitro cytotoxicity against acute myeloid leukemia cells and normal leukocytes using the bioassay of reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). The triazenes showed ability to cleave the two types of plasmid DNA: triazene 1 at pH 8.0 and 50 degrees C; triazene 2 at pH 6.5 and 37 and 50 degrees C; triazene 3 at pH 6.5 and 37 degrees C. The compounds presented cytotoxic activity against myeloid leukemia cells. Compound 1 showed high activity against B. cereus (MIC = 32 mu g mL(-1)). The observation of intermolecular hydrogen bonding in the solid state of compound 3, based on the structural analysis by X-ray crystallography, as well as the results of IR and UV-Vis spectroscopic analyses of compounds 1, 2 and 3 are discussed in the present work.