4-chloro-5-(1-naphthyloxy)-1,2-phenylenediamine | 786636-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-chloro-5-(1-naphthyloxy)-1,2-phenylenediamine
• 英文别名: 4-chloro-5-naphthalen-1-yloxybenzene-1,2-diamine
• CAS: 786636-31-5
• 化学式: C₁₆H₁₃ClN₂O
• 分子量: 284.745
• InChiKey: YGHDDCKSFUIOEO-UHFFFAOYSA-N

物化性质

• 沸点：
  473.4±45.0 °C(predicted)
• 密度：
  1.351±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-5-(1-naphthyloxy)-1,2-phenylenediamine 在 氢氧化钾 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 3.5h， 生成 5-chloro-2-(methylthio)-6-(1-naphthyloxy)-1H-benzimidazol
  参考文献：
  名称：

  Synthesis and Fasciolicidal Activity of 5-Chloro-2-methylthio-6-(1-naphthyloxy)-1H-benzimidazole.

  摘要：

  本文介绍了 5-氯-2-甲硫基-6-(1-萘氧基)-1H-苯并咪唑（6）的合成和杀筋膜活性。化合物 6 在 146.70 和 29.34 μ<小>M浓度下显示出 100% 的体外活性。在剂量为 15 毫克/千克时，它还能完全清除绵羊体内 3 d 和 10 周龄的肝脏法氏囊病菌。

  DOI：

  10.1248/cpb.50.649
• 作为产物：
  描述：

  4,5-二氯-2-硝基苯胺 在 potassium carbonate 、 tin(ll) chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 4-chloro-5-(1-naphthyloxy)-1,2-phenylenediamine
  参考文献：
  名称：

  Synthesis and Fasciolicidal Activity of 5-Chloro-2-methylthio-6-(1-naphthyloxy)-1H-benzimidazole.

  摘要：

  本文介绍了 5-氯-2-甲硫基-6-(1-萘氧基)-1H-苯并咪唑（6）的合成和杀筋膜活性。化合物 6 在 146.70 和 29.34 μ<小>M浓度下显示出 100% 的体外活性。在剂量为 15 毫克/千克时，它还能完全清除绵羊体内 3 d 和 10 周龄的肝脏法氏囊病菌。

  DOI：

  10.1248/cpb.50.649

文献信息

• Synthesis and biological activity of 2-(trifluoromethyl)-1H-benzimidazole derivatives against some protozoa and Trichinella spiralis
  作者：Francisco Hernández-Luis、Alicia Hernández-Campos、Rafael Castillo、Gabriel Navarrete-Vázquez、Olivia Soria-Arteche、Manuel Hernández-Hernández、Lilián Yépez-Mulia

  DOI：10.1016/j.ejmech.2010.03.050

  日期：2010.7

  mexicana, and they showed nanomolar activities against the first three protozoa tested. The compounds were also tested in vitro and in vivo against the nematode Trichinella spiralis. Compounds 1b, 1c and 1e had the most desirable in vitro antiparasitic profile against all parasites studied. In the in vivo model against T. spiralis, compounds 1b and 1e showed good activity against the adult phase at 75 mg/Kg

  通过取代的1,2-苯二胺和三氟乙酸的Phillips缩合反应，合成了一系列2-（三氟甲基）-1 H-苯并咪唑衍生物（1a – 1i）。对合成的化合物进行了体外抗多种原生动物寄生虫的评估：肠道贾第虫，溶血性变形杆菌，阴道毛滴虫和墨西哥利什曼原虫，它们显示出对前三个原生动物的纳摩尔活性。该化合物还进行了体外和体内针对线虫旋毛虫的测试。化合物1b，1c和1e对所有研究的寄生虫具有最理想的体外抗寄生虫特性。在针对螺旋旋毛虫的体内模型中，化合物1b和1e以75 mg / Kg的浓度对成年期表现出良好的活性。但是，针对肌肉幼虫阶段，仅化合物1f表现出体内抗寄生虫功效。
• Synthesis and in vitro cysticidal activity of new benzimidazole derivatives
  作者：Francisca Palomares-Alonso、Helgi Jung-Cook、Jaime Pérez-Villanueva、Juan Carlos Piliado、Sergio Rodríguez-Morales、Guadalupe Palencia-Hernández、Nayeli López-Balbiaux、Alicia Hernández-Campos、Rafael Castillo、Francisco Hernández-Luis

  DOI：10.1016/j.ejmech.2008.05.005

  日期：2009.4

  Despite albendazole being the drug of choice in neurocysticercosis treatment, its low solubility limits its bioavailability; therefore, more research is required in order to find new molecules with cestocidal activity and adequate aqueous solubility. A set of 13 benzimidazole derivatives were synthesized and their in vitro activities were evaluated against Taenia crassiceps cysts, using albendazole sulfoxide as reference molecule, showing that two of them exhibited good activity. Molecular modelling revealed that the cysticidal efficacy depends on the presence on the molecule of an H in the 1-position, a planar carbamate group at 2-position, and if the substituent in 5-position is voluminous, it should be orthogonal to the benzimidazole ring. (c) 2008 Elsevier Masson SAS. All rights reserved.
• Studies on 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole/2-hydroxypropyl-β-cyclodextrin association: Characterization, molecular modeling studies, and in vivo anthelminthic activity
  作者：Yareli Rojas-Aguirre、Lilián Yépez-Mulia、Ivan Castillo、Fabian López-Vallejo、Olivia Soria-Arteche、Alicia Hernández-Campos、Rafael Castillo、Francisco Hernández-Luis

  DOI：10.1016/j.bmc.2010.12.015

  日期：2011.1

  The purpose of this work is to study the molecular association that occurs between 2-hydroxypropyl-beta-cyclodextrin (HP beta CD) and 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole (RCB20), an antiparasitic compound recently found by our research group, with poor aqueous solubility. The complex stability constant and stoichiometric ratio determined by phase-solubility diagram and Job's plot provided evidence that HP beta CD enhanced water solubility of RCB20 through inclusion complex formation. Two-dimensional H-1 NMR spectroscopy is used to study the molecular arrangement of inclusion complex in solution. These results are further supported using molecular modeling studies. In the solid state, the complexation is confirmed by differential scanning calorimetry, powder X-ray diffraction, and scanning electron microscopy. Finally, RCB20/HP beta CD complex has better activity than RCB20 against the adult and muscle larvae phase of Trichinella spiralis. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and Fasciolicidal Activity of 5-Chloro-2-methylthio-6-(1-naphthyloxy)-1H-benzimidazole.
  作者：Alicia Hernández-Campos、Froylán Ibarra-Velarde、Yolanda Vera-Montenegro、Norma Rivera-Fernández、Rafael Castillo

  DOI：10.1248/cpb.50.649

  日期：——

  The synthesis and fasciolicidal activity of 5-chloro-2-methylthio-6-(1-naphthyloxy)-1H-benzimidazole (6) is described. Compound 6 showed 100% activity in vitro at 146.70 and 29.34 μM concentrations. It also completely removed 3-d and 10-week-old Fasciola hepatica in sheep at a dose of 15 mg/kg.

  本文介绍了 5-氯-2-甲硫基-6-(1-萘氧基)-1H-苯并咪唑（6）的合成和杀筋膜活性。化合物 6 在 146.70 和 29.34 μ<小>M浓度下显示出 100% 的体外活性。在剂量为 15 毫克/千克时，它还能完全清除绵羊体内 3 d 和 10 周龄的肝脏法氏囊病菌。