N,N'-bis[(1E)-(4-methoxyphenyl)methylene]benzene-1,4-diamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,N'-bis[(1E)-(4-methoxyphenyl)methylene]benzene-1,4-diamine
• 英文别名: N,N'-bis-(4-methoxybenzylidene)benzene-1,4-diamine
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: ZLMXOZRYFBGPHV-DFEHQXHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.18
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  巯基乙酸 、 N,N'-bis[(1E)-(4-methoxyphenyl)methylene]benzene-1,4-diamine 生成 p-bis[4-oxo-2-(p-methoxyphenyl)thiazolidin-3-yl]benzene
  参考文献：
  名称：

  DASH, B.;PRAHARAJ, S.;MOHAPATRA, P. K., J. INDIAN CHEM. SOC., 1981, 58, N 12, 1184-1186

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 对苯二胺 以 乙醇 为溶剂， 反应 3.0h， 以97%的产率得到N,N'-bis[(1E)-(4-methoxyphenyl)methylene]benzene-1,4-diamine
  参考文献：
  名称：

  N,N‘-Bisbenzylidenebenzene-1,4-diamines and N,N‘-Bisbenzylidenenaphthalene-1,4-diamines as Sirtuin Type 2 (SIRT2) Inhibitors

  摘要：

  A series of N,N'-bisbenzylidenebenzene-1,4-diamine and N,N'-bisbenzylidenenaphthalene-1,4-diamine derivatives were synthesized as inhibitors for human sirtuin type 2 (SIRT2). The design of the new compounds was based on two earlier reported hits from molecular modeling and virtual screening. The most potent compound was N,N'-bis(2-hydroxybenzylidene)benzene-1,4-diamine, which was equipotent with the most potent hit compound and well-known SIRT2 inhibitor sirtinol.

  DOI：

  10.1021/jm060566j

文献信息

• Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines
  作者：Xiaoying Zhang、Junhua Zhang、Zhiqiang Hao、Zhangang Han、Jin Lin、Guo-Liang Lu

  DOI：10.1021/acs.organomet.1c00552

  日期：2021.11.22

  characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine

  水杨醛配体的治疗L1H - L2H（L1H = 2,4-二-叔丁基-6 - （（喹啉-8-基亚氨基）甲基）苯酚; L2H = 2,4-二-叔丁基-6 - （（ (2-(二乙氨基)乙基)亚氨基)甲基)苯酚)与Ni(OAc) 2 ·4H 2 O在乙醇回流中得到镍配合物[( L1 )Ni(OAc)]( 1 )和[( L2 )Ni(OAc) )] ( 2 ) 分别。的反应L3H（L3H =（2,4-二-叔丁基-6 - （（（2-（吡啶-2-基）乙基）亚氨基）甲基）苯酚）），与镍（OAC）2 ·4H 2在过量三乙胺存在下，O 得到双配体配位的镍配合物 [( L2 ) 2 Ni] ( 3 )。配合物1 - 3分别充分表征通过高分辨率质谱法，红外光谱，元素分析，X-射线衍射分析。所有三种 Ni(II) 配合物在醇和胺的无受体脱氢偶联生成亚胺和二亚胺方面均表现出有效的活性和良好的选择性。本协议通过使用地球
• <i>N,N</i>‘-Bisbenzylidenebenzene-1,4-diamines and <i>N,N</i>‘-Bisbenzylidenenaphthalene-1,4-diamines as Sirtuin Type 2 (SIRT2) Inhibitors
  作者：Päivi H. Kiviranta、Jukka Leppänen、Sergiy Kyrylenko、Heikki S. Salo、Maija Lahtela-Kakkonen、Anu J. Tervo、Carsten Wittekindt、Tiina Suuronen、Erkki Kuusisto、Tomi Järvinen、Antero Salminen、Antti Poso、Erik A. A. Wallén

  DOI：10.1021/jm060566j

  日期：2006.12.1

  A series of N,N'-bisbenzylidenebenzene-1,4-diamine and N,N'-bisbenzylidenenaphthalene-1,4-diamine derivatives were synthesized as inhibitors for human sirtuin type 2 (SIRT2). The design of the new compounds was based on two earlier reported hits from molecular modeling and virtual screening. The most potent compound was N,N'-bis(2-hydroxybenzylidene)benzene-1,4-diamine, which was equipotent with the most potent hit compound and well-known SIRT2 inhibitor sirtinol.
• DASH, B.;PRAHARAJ, S.;MOHAPATRA, P. K., J. INDIAN CHEM. SOC., 1981, 58, N 12, 1184-1186
  作者：DASH, B.、PRAHARAJ, S.、MOHAPATRA, P. K.

  DOI：——

  日期：——
• PAXUROVA, T. F.;GUDRINIETSE, EH. YU.;PAULINSH, YA. YA.;KALNYNSH, A. P., IZV. AN LATVSSR. CEP. XIM., 1983, N 2, 225-228
  作者：PAXUROVA, T. F.、GUDRINIETSE, EH. YU.、PAULINSH, YA. YA.、KALNYNSH, A. P.

  DOI：——

  日期：——
• Palladium(II) imine ligands cyclometallated complexes with a potential leishmanicidal activity on Leishmania (L.) amazonensis
  作者：Lilian Pereira Franco、Elba Pereira de Góis、Bárbara Santoni Codonho、Ana Laura Raymundo Pavan、Ivan de Oliveira Pereira、Marcos José Marques、Eduardo Tonon de Almeida

  DOI：10.1007/s00044-012-0095-x

  日期：2013.3

  The leishmaniasis, considered a neglected disease, is caused by a protozoan from the genus Leishmania. There is an urgent need to search for safer, cheaper, and more effective treatments against leishmaniasis. In this context, transition metal complex activities have been studied, as palladium, which has become an interesting alternative as metal-based drugs. In this study, three new palladium(II) complexes, obtained from two imine ligands, were synthesized and characterized by elemental analyses, infrared and H-1 NMR spectroscopies. The in vitro evaluation of ligands and complexes has been tested on promastigote and amastigote forms of Leishmania (Leishmania) amazonensis and its cytotoxicity on murine macrophages. All complexes exhibited a leishmanicidal activity on promastigotes and amastigotes forms. The ligands activities were improved after coordination with palladium, and the replacement by some substituents has increased the leishmanicidal activity even more. Complexes with chloride and thiocyanate showed an improvement of activity when compared to their respective ligands, with better selectivity index (SI > 1) and less damage on mammalian cells when compared to a reference drug pentamidine. These compounds are promising agents for leishmaniasis treatment, and the results emphasize the potential properties of compounds with transition metal for medical applications.