(E)-2-((1,4-dimethylpiperazin-2-ylidene)amino)-N-(2-fluorophenyl)-5-nitrobenzamide | 1613465-36-3

• 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: (E)-2-((1,4-dimethylpiperazin-2-ylidene)amino)-N-(2-fluorophenyl)-5-nitrobenzamide
• CAS: 1613465-36-3
• 化学式: C₁₉H₂₀FN₅O₃
• 分子量: 385.398
• InChiKey: KKZUIWZVXFPMAU-DYTRJAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.08
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-(2-chloroacetamido)-5-nitrobenzoic acid 在 potassium carbonate 、 三氟乙酸 、 potassium iodide 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.25h， 生成 (E)-2-((1,4-dimethylpiperazin-2-ylidene)amino)-N-(2-fluorophenyl)-5-nitrobenzamide
  参考文献：
  名称：

  Development of (E)-2-((1,4-Dimethylpiperazin-2-ylidene)amino)-5-nitro-N-phenylbenzamide, ML336: Novel 2-Amidinophenylbenzamides as Potent Inhibitors of Venezuelan Equine Encephalitis Virus

  摘要：

  Venezuelan equine encephalitis virus (VEEV) is an emerging pathogenic alphavirus that can cause significant disease in humans. Given the absence of therapeutic options available and the significance of VEEV as a weaponized agent, an optimization effort was initiated around a quinazolinone screening hit 1 with promising cellular antiviral activity (EC50 = 0.8 mu M), limited cytotoxic liability (CC50 > 50 mu M), and modest in vitro efficacy in reducing viral progeny (63-fold at 5 mu M). Scaffold optimization revealed a novel rearrangement affording amidines, specifically compound 45, which was found to potently inhibit several VEEV strains in the low nanomolar range without cytotoxicity (EC50 = 0.02-0.04 mu M, CC50 > 50 mu M) while limiting in vitro viral replication (EC90 = 0.17 mu M). Brain exposure was observed in mice with 45. Significant protection was observed in VEEV-infected mice at 5 mg kg(-1) day(-1) and viral replication appeared to be inhibited through interference of viral nonstructural proteins.

  DOI：

  10.1021/jm501203v

文献信息

• [EN] 6-SUBSTITUTED QUINAZOLINONE INHIBITORS<br/>[FR] INHIBITEURS DE QUINAZOLINONE 6-SUBSTITUÉS
  申请人：UNIV KANSAS

  公开号：WO2014093869A1

  公开（公告）日：2014-06-19

  The present technology relates to compounds and compositions of Formulas I-III and methods using such compounds. The compounds and compositions described herein may be used in the treatment or prophylaxis of diseases associated with an alphavirus, for example, Venezuelan equine encephalitis virus (VEEV).

  这项技术涉及到I-III式化合物和组合物，以及使用这些化合物的方法。本文描述的化合物和组合物可用于治疗或预防与阿尔法病毒相关的疾病，例如委内瑞拉马蹄病毒（VEEV）。
• 6-SUBSTITUTED QUINAZOLINONE INHIBITORS
  申请人：UNIVERSITY OF KANSAS

  公开号：US20150329499A1

  公开（公告）日：2015-11-19

  The present technology relates to compounds and compositions of Formulas I-III and methods using such compounds. The compounds and compositions described herein may be used in the treatment or prophylaxis of diseases associated with an alphavirus, for example, Venezuelan equine encephalitis virus (VEEV).

  本技术涉及公式I-III的化合物和组合物以及使用此类化合物的方法。此处描述的化合物和组合物可用于治疗或预防与阿尔法病毒相关的疾病，例如委内瑞拉马蹄热病毒（VEEV）。
• 6-substituted quinazolinone inhibitors
  申请人：University of Kansas

  公开号：US10087168B2

  公开（公告）日：2018-10-02

  The present technology relates to compounds and compositions of Formulas I-III and methods using such compounds. The compounds and compositions described herein may be used in the treatment or prophylaxis of diseases associated with an alphavirus, for example, Venezuelan equine encephalitis virus (VEEV).

  本技术涉及式 I-III 的化合物和组合物以及使用此类化合物的方法。本文所述的化合物和组合物可用于治疗或预防与α-病毒（例如委内瑞拉马脑炎病毒（VEEV））相关的疾病。
• Lipid-coated particles for treating viral infections
  申请人：National Technology & Engineering Solutions of Sandia, LLC

  公开号：US11045554B1

  公开（公告）日：2021-06-29

  The present invention relates to lipid-coated particles for treating viral infections, including viral encephalitis infections. In particular, an antiviral compound can be disposed within the lipid-coated particle, thereby providing an antiviral carrier. Methods of making and using such carriers are described herein.

  本发明涉及用于治疗病毒感染（包括病毒性脑炎感染）的脂质包衣颗粒。特别是，抗病毒化合物可置于脂质包衣颗粒内，从而提供一种抗病毒载体。本文描述了制造和使用这种载体的方法。
• LIPID-COATED PARTICLES FOR TREATING VIRAL INFECTIONS
  申请人：National Technology & Engineering Solutions of Sandia, LLC

  公开号：US20210330809A1

  公开（公告）日：2021-10-28

  The present invention relates to lipid-coated particles for treating viral infections, including viral encephalitis infections. In particular, an antiviral compound can be disposed within the lipid-coated particle, thereby providing an antiviral carrier. Methods of making and using such carriers are described herein.