5-(N,N-dimethylamino)-2,4-dinitroaniline

• 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-(N,N-dimethylamino)-2,4-dinitroaniline
• 英文别名: 3-N,3-N-dimethyl-4,6-dinitrobenzene-1,3-diamine
• 化学式: C₈H₁₀N₄O₄
• 分子量: 226.192
• InChiKey: VOOWZUOSJBZVMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(N,N-dimethylamino)-2,4-dinitroaniline 在 吡啶 、 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 5-butyloxycarbonylamino-2-cyclohexyl-6-(N,N-dimethylamino)-1H-benzo[d]imidazole
  参考文献：
  名称：

  SAR Studies on Trisubstituted Benzimidazoles as Inhibitors of Mtb FtsZ for the Development of Novel Antitubercular Agents

  摘要：

  FtsZ, an essential protein for bacterial cell division, is a highly promising therapeutic target, especially for the discovery and development of new-generation anti-TB agents. Following up the identification of two lead 2,5,6-trisubstituted benzimidazoles, 1 and 2, targeting Mtb-FtsZ in our previous study, an extensive SAR study for optimization of these lead compounds was performed through systematic modification of the 5 and 6 positions. This study has successfully led to the discovery of a highly potent advanced lead 5f (MIC = 0.06 mu g/mL) and several other compounds with comparable potencies. These advanced lead compounds possess a dimethylamino group at the 6 position. The functional groups at the 5 position exhibit substantial effects on the antibacterial activity as well. In vitro experiments such as the FtsZ polymerization inhibitory assay and TEM analysis of Mtb-FtsZ treated with 5f and others indicate that Mtb-FtsZ is the molecular target for their antibacterial activity.

  DOI：

  10.1021/jm401468w
• 作为产物：
  描述：

  N,N-dimethyl-3,4-dinitroaniline 在 乙醇 、 氨 、 硝酸 作用下， 生成 5-(N,N-dimethylamino)-2,4-dinitroaniline
  参考文献：
  名称：

  Forster; Coulson, Journal of the Chemical Society, 1922, vol. 121, p. 1995

  摘要：

  DOI：

文献信息

• Structure–activity relationship studies on 2,5,6-trisubstituted benzimidazoles targeting <i>Mtb</i>-FtsZ as antitubercular agents
  作者：Krupanandan Haranahalli、Simon Tong、Saerom Kim、Monaf Awwa、Lei Chen、Susan E. Knudson、Richard A. Slayden、Eric Singleton、Riccardo Russo、Nancy Connell、Iwao Ojima

  DOI：10.1039/d0md00256a

  日期：——

  new antibacterial therapeutics. As a part of our ongoing SAR studies on 2,5,6-trisubstituted benzimidazoles as antitubercular agents targeting Mtb-FtsZ, a new library of compounds with modifications at the 2 position was designed, synthesized and evaluated for their activity against Mtb-H37Rv. This new library of trisubstituted benzimidazoles exhibited MIC values in the range of 0.004–50 μg mL−1. Compounds

  丝状温度敏感蛋白 Z (FtsZ) 是一种必需的细菌细胞分裂蛋白，也是开发新抗菌疗法的有希望的靶点。作为我们正在进行的关于 2,5,6-三取代苯并咪唑作为靶向Mtb -FtsZ 的抗结核药物的 SAR 研究的一部分，设计、合成了一个在 2 位进行修饰的新化合物库，并评估了它们对Mtb -H37Rv的活性。这个新的三取代苯并咪唑文库的 MIC 值在 0.004–50 μg mL -1范围内。化合物6b、6c、20f和20g在 0.004–0.08 μg mL -1范围内表现出优异的生长抑制活性. 该 SAR 研究导致发现了一种非常有效的化合物20g（MIC 0.0039 μg mL -1；标准化 MIC 0.015 μg mL -1）。我们的 3DQSAR 模型预测20g是库中最有效的化合物。
• [EN] BENZIMIDAZOLES AND THEIR USE IN THE TREATMENT OF TUBERCULOSIS<br/>[FR] BENZIMIDAZOLES ET LEUR UTILISATION DANS LE TRAITEMENT DE LA TUBERCULOSE
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2015077276A1

  公开（公告）日：2015-05-28

  The present invention relates to novel 2,5,6- benzimidazole derivatives and pharmaceutically acceptable salts thereof. Another aspect of the invention relates to methods of treating a patient infected by Mycobacterium tuberculosis by administering to the patient a 2,5,6- benzimidazole derivative or a pharmaceutically acceptable salt thereof.

  本发明涉及新型2,5,6-苯并咪唑衍生物及其药用盐。发明的另一个方面涉及通过向患有结核分枝杆菌感染的患者投与2,5,6-苯并咪唑衍生物或其药用盐来治疗患者的方法。
• van Romburgh; Wensink, Verslag van de Gewone Vergadering van de Afdeling Natuurkunde, Koninklijke Nederlandse Akademie van Wetenschappen, 1914, vol. 23, p. 967
  作者：van Romburgh、Wensink

  DOI：——

  日期：——
• Benzimidazoles and Their Use in the Treatment of Tuberculosis
  申请人：THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK

  公开号：US20160297769A1

  公开（公告）日：2016-10-13

  The present invention relates to novel 2,5,6-benzimidazole derivatives and pharmaceutically acceptable salts thereof. Another aspect of the invention relates to methods of treating a patient infected by Mycobacterium tuberculosis by administering to the patient a 2,5,6-benzimidazole derivative or a pharmaceutically acceptable salt thereof.
• US9845296B2
  申请人：——

  公开号：US9845296B2

  公开（公告）日：2017-12-19