1-(4-benzotriazol-1-yl-phenyl)ethanone | 728-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-benzotriazol-1-yl-phenyl)ethanone
• 英文别名: 1-(4'-acetylphenyl)benzotriazole；4-benzotriazole acetophenone；1-(4-benzotriazol-1-yl-phenyl)-ethanone；1-[4-(Benzotriazol-1-yl)phenyl]ethanone
• CAS: 728-23-4
• 化学式: C₁₄H₁₁N₃O
• mdl: MFCD10693360
• 分子量: 237.261
• InChiKey: QMHZKDFFGAEWOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-benzotriazol-1-yl-phenyl)ethanone 、 1H-苯并咪唑-2-硫醇 在 硫酸 、 溶剂黄146 作用下， 反应 1.0h， 以89%的产率得到2-[(2-(4-(1H-benzo[d][1,2,3]triazol-1-yl)phenyl)-2-oxoethyl)thio]-1H-benzo[d]imidazol-3-ium sulfate
  参考文献：
  名称：

  通过抑制c-MET激酶合成一些新型的抗苯恶唑硫代苯并咪唑衍生物并对其进行生物学评估。

  摘要：

  苯并咪唑是一种有趣的支架，构成了抗多菌灵（I）和诺考达唑（II）等多种细胞系抗癌剂的主要核心。因此，设计并研究了十八种硫酸盐和游离形式的2-（（1H-苯并咪唑-2-基）硫基）-1-（芳基/杂芳基）乙-1-酮的化合物作为抗癌剂并进行了研究。美国国家癌症研究所（NCI）对60种细胞系进行了体外初步筛选，发现肾癌细胞系（A498）是最脆弱的细胞系。因此，对于具有最佳结果的化合物，确定了针对A498细胞系的IC50值。与舒尼替尼作为参考药物（IC50 = 6.99 µM）相比，对化合物4a的最佳抑制活性为（IC50 = 6.97 µM）。对化合物4a进一步进行细胞周期分析，表明与未处理的对照细胞相比，G2 / M期的细胞数量减少。此外，与对照细胞相比，膜联蛋白-V FTIC研究显示其晚期细胞凋亡显着增加。一项针对c-Met和MAP激酶的化合物4a的酶促抑制研究显示，与舒尼替尼（IC50 = 0.18

  DOI：

  10.1016/j.bioorg.2019.01.006
• 作为产物：
  描述：

  4-氟苯乙酮 以9%的产率得到
  参考文献：
  名称：

  LIN J.; RIVETT D. E.; WILSHIRE J. F. K., AUSTRAL. J. CHEM. , 1977, 30, NO 3, 629-637

  摘要：

  DOI：

文献信息

• Copper−Diamine-Catalyzed <i>N</i>-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles
  作者：Jon C. Antilla、Jeremy M. Baskin、Timothy E. Barder、Stephen L. Buchwald

  DOI：10.1021/jo049658b

  日期：2004.8.1

  This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as

  本文详细介绍了铜催化的π-过量氮杂环的N-芳基化反应。芳基碘化物或芳基溴化物与常见的氮杂环（吡咯，吡唑，吲唑，咪唑和三唑）的偶联成功地用衍生自二胺配体和CuI的催化剂进行了高收率的偶联。发现一般条件可耐受芳基卤化物或杂环上的官能团，例如醛，酮，醇，伯胺和腈。使用本文报道的条件，受阻的芳基卤化物或杂环也被发现是合适的底物。
• Cu(OAc)2·H2O-catalyzed N-arylation of nitrogen-containing heterocycles
  作者：Zhong-Lin Xu、Hong-Xi Li、Zhi-Gang Ren、Wei-Yuan Du、Wei-Chang Xu、Jian-Ping Lang

  DOI：10.1016/j.tet.2011.05.025

  日期：2011.7

  In the absence of any additional ligands, the efficient N-arylation of nitrogen-containing heterocycles with aryl iodides catalyzed by relative low catalyst amount of Cu(OAc)2·H2O was developed. This simple catalytic system is involved in the C–N cross-coupling reaction and works for a variety of pyrazole, pyrrole, imidazole, triazole, indole, benzoimidazole, benzotriazole, carbazole, and anilines

  在没有任何其他配体的情况下，开发了由相对较低的催化剂量的Cu（OAc）2 ·H 2 O催化的含氮杂环与芳基碘的有效N-芳基化反应。这种简单的催化系统参与C–N交叉偶联反应，适用于各种电子性质不同的各种吡唑，吡咯，咪唑，三唑，吲哚，苯并咪唑，苯并三唑，咔唑和苯胺以及碘代芳基碘。建立了高效的铜（II）催化的N-芳基化方案。
• Synthesis of novel substituted 1,3-diaryl propenone derivatives and their antimalarial activity in vitro
  作者：Nidhi Mishra、Preeti Arora、Brajesh Kumar、Lokesh C. Mishra、Amit Bhattacharya、Satish K. Awasthi、Virendra K. Bhasin

  DOI：10.1016/j.ejmech.2007.09.014

  日期：2008.7

  The synthesis of novel 1,3-diaryl propenone derivatives and their antimalarial activity in vitro against asexual blood stages of human malaria parasite, Plasmodium falciparum, are described. Chalcone derivatives were prepared via Claisen-Schmidt condensation of substituted aldehydes with substituted methyl ketones. Antiplasmodial IC(50) (half maximal inhibitory concentration) activity of these compounds

  描述了新型1，3-二芳基丙烯酮衍生物的合成及其体外抗人疟疾寄生虫恶性疟原虫无性血液阶段的抗疟活性。通过取代的醛与取代的甲基酮的克莱森-施密特缩合制备查耳酮衍生物。这些化合物的抗血浆IC（50）（最大抑制浓度的一半）活性介于1.5和12.3 microg / ml之间。发现氯系列1,2,4-三唑取代的查尔酮在体外抑制恶性疟原虫的生长最有效，而吡咯和苯并三唑取代的查耳酮则显示出相对较低的抑制活性。这是有关苯乙酮环上的查尔酮类与吡咯类抗疟原虫活性的首次报道。
• Pd- and Cu-catalyzed selective arylation of benzotriazole
  作者：Irina P. Beletskaya、Dmitri V. Davydov、Marcial Moreno-Mañas

  DOI：10.1016/s0040-4039(98)01062-4

  日期：1998.7

  Palladium(O)-catalyzed arylation of 1H-1,2,3-benzotriazole (BTA) in DMF at 150 degrees C in the presence of copper salt with arylhalides proceeds regioselectively at N-1 position. Best result has been obtained with the PdCl2(dppe) as catalyst and the Cu(II) phenylcyclopropylcarboxylate as co-catalyst. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Antimalarial Activity of Newly Synthesized Chalcone Derivatives In Vitro
  作者：Neesha Yadav、Sandeep K. Dixit、Amit Bhattacharya、Lokesh C. Mishra、Manish Sharma、Satish K. Awasthi、Virendra K. Bhasin

  DOI：10.1111/j.1747-0285.2012.01383.x

  日期：2012.8

  Twenty‐seven novel chalcone derivatives were synthesized using Claisen‐Schmidt condensation and their antimalarial activity against asexual blood stages of Plasmodium falciparum was determined. Antiplasmodial IC50 (half‐maximal inhibitory concentration) activity of a compound against malaria parasites in vitro provides a good first screen for identifying the antimalarial potential of the compound. The most active compound was 1‐(4‐benzimidazol‐1‐yl‐phenyl)‐3‐(2, 4‐dimethoxy‐phenyl)‐propen‐1‐one with IC50 of 1.1 μg/mL, while that of the natural phytochemical, licochalcone A is 1.43 μg/mL. The presence of methoxy groups at position 2 and 4 in chalcone derivatives appeared to be favorable for antimalarial activity as compared to other methoxy‐substituted chalcones. Furthermore, 3, 4, 5‐trimethoxy groups on chalcone derivative probably cause steric hindrance in binding to the active site of cysteine protease enzyme, explaining the relative lower inhibitory activity.