2-(2H-indazol-2-yl)-1-(4-nitrophenyl)ethan-1-one | 1362690-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2H-indazol-2-yl)-1-(4-nitrophenyl)ethan-1-one
• 英文别名: 2-(2H-indazol-2-yl)-1-(4-nitrophenyl)-ethanone；2-Indazol-2-yl-1-(4-nitrophenyl)ethanone
• CAS: 1362690-72-9
• 化学式: C₁₅H₁₁N₃O₃
• 分子量: 281.271
• InChiKey: YKLMJRWVTCBIMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吲唑 、 2-溴-4'-硝基苯乙酮 反应 1.5h， 以73%的产率得到2-(2H-indazol-2-yl)-1-(4-nitrophenyl)ethan-1-one
  参考文献：
  名称：

  Novel inhibitors of nitric oxide synthase with antioxidant properties

  摘要：

  We previously described a series of imidazole-based inhibitors substituted at N-1 with an arylethanone chain as interesting inhibitors of neuronal nitric oxide synthase (nNOS), endowed with good selectivity vs endothelial nitric oxide synthase (eNOS). As a follow up of these studies, several analogs characterized by the presence of substituted imidazoles or other mono or bicyclic nitrogen-containing heterocycles instead of simple imidazole were synthesized, and their biological evaluation as in vitro inhibitors of both nNOS and eNOS is described herein. Most of these compounds showed improved nNOS and eNOS inhibitory activity with respect to reference inhibitors. Selected compounds were also tested to analyze their antioxidant properties. Some of them displayed good capacity to scavenge free radicals and ability to reduce lipid peroxidation. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.002

文献信息

• TfOH-catalyzed regioselective <i>N</i>²-alkylation of indazoles with diazo compounds
  作者：Hangli He、Jingyu Yan、Jingru Jin、Zhewei Yan、Qiongjiao Yan、Wei Wang、Haipeng Jiang、Haifeng Wang、Fener Chen

  DOI：10.1039/d2cc01404a

  日期：——

  Selective alkylation of indazoles is still a highly challenging topic in chemistry and the synthesis of important molecules. Herein, a novel highly selective N2-alkylation of indazoles with diazo compounds is described in the presence of TfOH. Unlike the traditional metal- and base-catalysed version, this protocol highlights the regioselectivity of alkylation of indazoles and a metal-free catalysis

  吲唑的选择性烷基化仍然是化学和重要分子合成中极具挑战性的课题。在此，描述了在 TfOH 存在下，吲唑与重氮化合物的新型高选择性N 2 -烷基化。与传统的金属和碱催化版本不同，该方案突出了吲唑烷基化的区域选择性和无金属催化体系，以高区域选择性（ N 2 / N 1高达 100/0) 和出色的官能团耐受性。此外，成功地进行了克级合成以产生相应的产物。通过控制实验进行的机械研究提供了合理的机械建议。
• Novel inhibitors of nitric oxide synthase with antioxidant properties
  作者：Loredana Salerno、Maria N. Modica、Giuseppe Romeo、Valeria Pittalà、Maria A. Siracusa、Maria E. Amato、Rosaria Acquaviva、Claudia Di Giacomo、Valeria Sorrenti

  DOI：10.1016/j.ejmech.2012.01.002

  日期：2012.3

  We previously described a series of imidazole-based inhibitors substituted at N-1 with an arylethanone chain as interesting inhibitors of neuronal nitric oxide synthase (nNOS), endowed with good selectivity vs endothelial nitric oxide synthase (eNOS). As a follow up of these studies, several analogs characterized by the presence of substituted imidazoles or other mono or bicyclic nitrogen-containing heterocycles instead of simple imidazole were synthesized, and their biological evaluation as in vitro inhibitors of both nNOS and eNOS is described herein. Most of these compounds showed improved nNOS and eNOS inhibitory activity with respect to reference inhibitors. Selected compounds were also tested to analyze their antioxidant properties. Some of them displayed good capacity to scavenge free radicals and ability to reduce lipid peroxidation. (C) 2012 Elsevier Masson SAS. All rights reserved.