5-nitro-1-tosyl-benzimidazole | 96954-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-nitro-1-tosyl-benzimidazole
• 英文别名: 1--5-nitro-benzimidazol；5-nitro-1-(toluene-4-sulfonyl)-1H-benzoimidazole；5-Nitro-1-tosylbenzimidazole；1-(4-methylphenyl)sulfonyl-5-nitrobenzimidazole
• CAS: 96954-21-1
• 化学式: C₁₄H₁₁N₃O₄S
• 分子量: 317.325
• InChiKey: VSGQIMHWNHRKJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-nitro-1-tosyl-benzimidazole 在 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-3-(3-(1-p-tosyl-1H-benzimidazol-5-yl)ureido)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one
  参考文献：
  名称：

  1,3-Disubstituted benzazepines as neuropeptide Y Y1 receptor antagonists

  摘要：

  A nuclei, have been designed, synthesized, and evaluated for activity. Through a blind screening we found the compound 1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-7-methoxy-(3-(3)-methylureido)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (9: IC50 = 1.6 mu M). Chemical modifications of 9 gave a potent NPY Y1 antagonist 3-(N-(4-hydroxyphenyl)-N'-methylguanidino)-1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (14c: IC50 = 43 nM), which had no affinity for NPY Y2 and Y5 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00087-5
• 作为产物：
  描述：

  4-硝基邻苯二胺 在 盐酸 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 生成 5-nitro-1-tosyl-benzimidazole
  参考文献：
  名称：

  Rashid, Naghmana; Kiran, Almas; Ashraf, Zaman, Journal of the Chemical Society of Pakistan, 2018, vol. 40, # 2, p. 366 - 374

  摘要：

  DOI：

文献信息

• A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides
  作者：Wanwan Sun、Xiaobei Chen、Ying Hu、Huihui Geng、Yuanrui Jiang、Yuxin Zhou、Wenjing Zhu、Min Hu、Haohua Hu、Xingyi Wang、Xinli Wang、Shilei Zhang、Yanwei Hu

  DOI：10.1016/j.tetlet.2020.152442

  日期：2020.10

  features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.

  据报道，由NaH介导的各种Ts保护的吲哚，氮杂杂环，苯胺和二苄基胺的解毒反应。该方法试剂便宜，操作方便，反应条件温和，底物范围广。此外，这项研究表明，由于可能发生不利的脱甲苯基作用，因此应控制在含氮化合物以NaH为碱的含氮化合物甲苯磺酸化反应中NaH的负载量。
• Antithrombotic agents
  申请人：Eli Lilly and Company

  公开号：US06372759B1

  公开（公告）日：2002-04-16

  This application relates to a compound of formula (I), a pharmaceutically acceptable salt of the compound, or a prodrug thereof, as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.

  该申请涉及公式(I)的化合物，该化合物的药学上可接受的盐，或者其前药，如本文所定义的，以及其药物组合物，以及其用作因子Xa抑制剂的用途，以及其制备过程和中间体。
• 1,3-Disubstituted benzazepines as neuropeptide Y Y1 receptor antagonists
  作者：Yasushi Murakami、Sanji Hagishita、Tetsuo Okada、Makoto Kii、Hiroshi Hashizume、Tatsuroh Yagami、Masafumi Fujimoto

  DOI：10.1016/s0968-0896(99)00087-5

  日期：1999.8

  A nuclei, have been designed, synthesized, and evaluated for activity. Through a blind screening we found the compound 1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-7-methoxy-(3-(3)-methylureido)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (9: IC50 = 1.6 mu M). Chemical modifications of 9 gave a potent NPY Y1 antagonist 3-(N-(4-hydroxyphenyl)-N'-methylguanidino)-1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (14c: IC50 = 43 nM), which had no affinity for NPY Y2 and Y5 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.
• ANTITHROMBOTIC AGENTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1019045B1

  公开（公告）日：2005-06-08
• US6372759B1
  申请人：——

  公开号：US6372759B1

  公开（公告）日：2002-04-16