4-(4H-1,2,4-三唑-4-基)苯甲腈 | 299914-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(4H-1,2,4-三唑-4-基)苯甲腈
• 英文名称: 4-(4H-1,2,4-triazol-4-yl)benzonitrile
• 英文别名: 4-(1,2,4-triazol-4-yl)benzonitrile
• CAS: 299914-43-5
• 化学式: C₉H₆N₄
• 分子量: 170.173
• InChiKey: BSKCKUGMHOONIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4H-1,2,4-三唑-4-基)苯甲腈 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 水 为溶剂， 反应 2.5h， 以84%的产率得到4-(4-(aminomethyl)phenyl)-4H-1,2,4-triazole
  参考文献：
  名称：

  Isoindolinone Inhibitors of the Murine Double Minute 2 (MDM2)-p53 Protein−Protein Interaction: Structure−Activity Studies Leading to Improved Potency

  摘要：

  Inhibition of the MDM2-p53 interaction has been shown to produce an antitumor effect, especially in MDM2 amplified tumors.. The isoindolinone scaffold has proved to be versatile for the discovery of MDM2-p53 antagonists. Optimization of previously reported inhibitors, for example, NU8231 (7) and NU8165 (49), was guided by MDM2 NMR titrations, which indicated key areas of the binding interaction to be explored. Variation of the 2-N-benzyl and 3-alkoxy substituents resulted in the identification of 3-(4-nitrobenzyl)-3-((1-(hydroxymethyl)cyclopropyl)methoxy)-2-(4-nitrobenzyl)isoindolin-1-one (74) as a potent MDM2-p53 inhibitor (IC(50) = 0.23 +/- 0.01 mu M). Resolution of the enantiomers of 74 showed that potent MDM2-p53 activity primarily resided with the (+)R-enantiomer (74a; IC(50) = 0.17 +/- 0.02 mu M). The cellular activity of key compounds has been examined in cell lines with defined p53 and MDM2 status. Compound 74a activates p53, MDM2, and p21 transcription in MDM2 amplified cells and shows moderate selectivity for wild-type p53 cell lines in growth inhibition assays.

  DOI：

  10.1021/jm1011929
• 作为产物：
  描述：

  N,N'-bis(dimethylaminomethylene)hydrazine 、 对氨基苯腈 以 甲苯 为溶剂， 以98%的产率得到4-(4H-1,2,4-三唑-4-基)苯甲腈
  参考文献：
  名称：

  Isoindolinone Inhibitors of the Murine Double Minute 2 (MDM2)-p53 Protein−Protein Interaction: Structure−Activity Studies Leading to Improved Potency

  摘要：

  Inhibition of the MDM2-p53 interaction has been shown to produce an antitumor effect, especially in MDM2 amplified tumors.. The isoindolinone scaffold has proved to be versatile for the discovery of MDM2-p53 antagonists. Optimization of previously reported inhibitors, for example, NU8231 (7) and NU8165 (49), was guided by MDM2 NMR titrations, which indicated key areas of the binding interaction to be explored. Variation of the 2-N-benzyl and 3-alkoxy substituents resulted in the identification of 3-(4-nitrobenzyl)-3-((1-(hydroxymethyl)cyclopropyl)methoxy)-2-(4-nitrobenzyl)isoindolin-1-one (74) as a potent MDM2-p53 inhibitor (IC(50) = 0.23 +/- 0.01 mu M). Resolution of the enantiomers of 74 showed that potent MDM2-p53 activity primarily resided with the (+)R-enantiomer (74a; IC(50) = 0.17 +/- 0.02 mu M). The cellular activity of key compounds has been examined in cell lines with defined p53 and MDM2 status. Compound 74a activates p53, MDM2, and p21 transcription in MDM2 amplified cells and shows moderate selectivity for wild-type p53 cell lines in growth inhibition assays.

  DOI：

  10.1021/jm1011929

文献信息

• Triazolyl, Imidazolyl, and Carboxylic Acid Moieties in the Design of Molybdenum Trioxide Hybrids: Photophysical and Catalytic Behavior
  作者：Andrey B. Lysenko、Ganna A. Senchyk、Konstantin V. Domasevitch、Merten Kobalz、Harald Krautscheid、Jakub Cichos、Miroslaw Karbowiak、Patrícia Neves、Anabela A. Valente、Isabel S. Gonçalves

  DOI：10.1021/acs.inorgchem.6b02986

  日期：2017.4.17

  Three organic ligands bearing 1,2,4-triazolyl donor moieties, (S)-4-(1-phenylpropyl)-1,2,4-triazole (trethbz), 4-(1,2,4-triazol-4-yl)benzoic acid (trPhCO2H), and 3-(1H-imidazol-4-yl)-2-(1,2,4-triazol-4-yl)propionic acid (trhis), were prepared to evaluate their coordination behavior in the development of molybdenum(VI) oxide organic hybrids. Four compounds, [Mo2O6(trethbz)2]·H2O (1), [Mo4O12(trPhCO2H)2]·0

  带有1,2,4-三唑基供体部分的三个有机配体，（S）-4-（1-苯丙基）-1,2,4-三唑（trethbz），4-（1,2,4-三唑-4-制备了yl）苯甲酸（trPhCO 2 H）和3-（1 H-咪唑-4-基）-2-（1,2,4-三唑-4-基）丙酸（trhis）以评估它们的氧化钼（VI）有机杂化物的发展中的配位行为。四种化合物[Mo 2 O 6（trethbz）2 ]·H 2 O（1），[Mo 4 O 12（trPhCO 2 H）2]·0.5H 2 O（2a），[Mo 4 O 12（trPhCO 2 H）2 ]·H 2 O（2b）和[Mo 8 O 25（trhis）2（trhisH）2 ]·2H 2 O（3），被合成和表征。单官能TR -配体导致Z字形链的形成[沫2 ö 6（trethbz）2 ]从建立了顺式- 的MoO 4Ñ 2通过普通联合}八面体μ 2个-O顶点。使用具有tr / –CO
• Process for the arylation of aza-heterocycles with activated aromatics in presence of caesium carbonate
  申请人：——

  公开号：US20040249185A1

  公开（公告）日：2004-12-09

  The invention concerns a process for the preparation of N-aryl-aza-heterocycles of the general formula I 1 by reaction of aza-heterocycles with activated aryl halides with use of caesium carbonate without addition of further catalysts at room temperature.

  本发明涉及通式 I 的 N-芳基氮杂环的制备工艺 1 在不添加其他催化剂的情况下，使用碳酸铯在室温下使氮杂环与活化的芳基卤化物反应。
• VERFAHREN ZUR HERSTELLUNG VON N-ARYL-AZA-HETEROCYCLEN IN GEGENWART VON CESIUMCARBONAT
  申请人：GÖDECKE GMBH

  公开号：EP1165512A2

  公开（公告）日：2002-01-02
• US6774242B1
  申请人：——

  公开号：US6774242B1

  公开（公告）日：2004-08-10
• US6933390B2
  申请人：——

  公开号：US6933390B2

  公开（公告）日：2005-08-23