α-(N-benzotriazol-1-yl)acetophenone phenylhydrazone | 127876-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: α-(N-benzotriazol-1-yl)acetophenone phenylhydrazone
• 英文别名: N-[[2-(benzotriazol-1-yl)-1-phenylethylidene]amino]aniline
• CAS: 127876-41-9
• 化学式: C₂₀H₁₇N₅
• 分子量: 327.388
• InChiKey: GQNTYRSRYVLQIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(benzotriazol-1-yl)acetophenone 、 苯肼 以 乙醇 为溶剂， 生成 α-(N-benzotriazol-1-yl)acetophenone phenylhydrazone
  参考文献：
  名称：

  Azolyacetones as Precursors to Indoles and Naphthofurans Facilitated by Microwave Irradiation with Simultaneous Cooling

  摘要：

  在微波辐照下，邻苯二甲酰亚胺与苯酰溴反应生成苯酰异吲哚-1,3-二酮（3b），而 3a 与苯肼反应生成苯腙 4，后者很容易转化为吲哚酰邻苯二甲酰亚胺 8。同样，N-苯并三唑基丙酮（6a）与苯肼反应生成苯腙 7a，并转化为吲哚基苯并三唑 9。用肼水合物处理 8，可得到酞酰肼 10 和 3-氨基-2-甲基吲哚（11）的混合物。将烯丙酮 13 与萘醌（14）反应，可得到芳基萘呋喃 17。根据 HMQC，羰基碳没有与任何氢相连，因此排除了形成醛 18 的可能性。

  DOI：

  10.3390/molecules14082976

文献信息

• Azolyacetones as Precursors to Indoles and Naphthofurans Facilitated by Microwave Irradiation with Simultaneous Cooling
  作者：Saleh Al-Mousawi、Morsy El-Apasery

  DOI：10.3390/molecules14082976

  日期：——

  Phthalimide reacted with phenacyl bromide under microwave irradiation to yield phenacyl isoindolidene-1,3-dione (3b), while 3a reacted with phenylhydrazine to yield the phenylhydrazone 4 that was readily converted into indoylphthalimide 8. Similarly N-benzotriazolylacetone (6a) reacted with phenyl hydrazine to yield the phenylhydrazone 7a that was converted into indoylbenzotriazole 9. Treatment of 8 with hydrazine hydrate afforded a mixture of phthalhydrazide 10 and 3-amino-2-methylindole (11). Reacting enaminone 13 with naphthoquinone (14) afforded the aryl naphthofuran 17. The possibility of the formation of the aldehyde 18 was excluded based on HMQC, which revealed that the carbonyl carbon is not linked to any hydrogen.

  在微波辐照下，邻苯二甲酰亚胺与苯酰溴反应生成苯酰异吲哚-1,3-二酮（3b），而 3a 与苯肼反应生成苯腙 4，后者很容易转化为吲哚酰邻苯二甲酰亚胺 8。同样，N-苯并三唑基丙酮（6a）与苯肼反应生成苯腙 7a，并转化为吲哚基苯并三唑 9。用肼水合物处理 8，可得到酞酰肼 10 和 3-氨基-2-甲基吲哚（11）的混合物。将烯丙酮 13 与萘醌（14）反应，可得到芳基萘呋喃 17。根据 HMQC，羰基碳没有与任何氢相连，因此排除了形成醛 18 的可能性。
• Katritzky, Alan R.; Wrobel, Leszek; Savage, G. Paul, Australian Journal of Chemistry, 1990, vol. 43, # 1, p. 133 - 139
  作者：Katritzky, Alan R.、Wrobel, Leszek、Savage, G. Paul、Deyrup-Drewniak, Malgorzata

  DOI：——

  日期：——
• Structure–cytotoxicity relationship of a novel series of miconazole-like compounds
  作者：Reza Yousefi、Ali Khalafi-Nezhad、Mohammad Navid Soltani Rad、Somayeh Behrouz、Farhad Panahi、Mansoore Esmaili、Sayed Mahmoud Ghaffari、Ali Niazi、Ali Akbar Moosavi-Movahedi

  DOI：10.1007/s00044-011-9716-z

  日期：2012.8

  In the current study, two novel classes of the carboacyclic nucleosides having miconazole-like scaffolds as imidazole- and pyrimidine-based compounds were examined for their cytotoxic properties. The aim was to establish a relation between cytotoxic activity and nature of the synthetic compounds. While Escherichia coli (DH5 alpha) and human erythromyeloblastoid leukemia cell line (K562) were the target cells, depending on the type of substitution made, ranges of antibacterial and antineoplastic activities were observed. Also the electron-donating and electron-accepting properties of the ligands were proved to play a crucial role in their cytotoxic activities. Accordingly, the substitutions associated with the marked improvement of cytotoxic activities can be considered as the significant point in construction of new generation of either antibacterial or antineoplastic agents.