N-(2,4-dichlorophenyl)-1-hydroxynaphthalene-2-carboxamide | 68352-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2,4-dichlorophenyl)-1-hydroxynaphthalene-2-carboxamide
• 英文别名: 1-hydroxy-naphthalene-2-carboxylic acid 2,4-dichloro-anilide
• CAS: 68352-26-1
• 化学式: C₁₇H₁₁Cl₂NO₂
• 分子量: 332.186
• InChiKey: NMBIEDDOWOHSHI-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  435.5±45.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2,4-dichlorophenyl)-1-hydroxynaphthalene-2-carboxamide 、 氯甲酸乙酯 生成 3-(2,4-dichloro-phenyl)-naphtho[2,1-e][1,3]oxazine-2,4-dione
  参考文献：
  名称：

  Synthesis of substituted 1-hydroxy-2-naphthanilides as potential cestodicidal agents

  摘要：

  A series of substituted 1-hydroxy-2-naphthanilides 4--14 has been synthesized by treating 1-hydroxy-2-naphthoic acids 2 with substituted anilines 3. The nitronaphthanilides, on reduction and subsequent treatment with thiophosgene, gave the corresponding substituted 2-naphthanilide isothiocyanates 30--33. Substitution of the chlorine of 8 by various cyclic amines gave 3'-nitro-4'-substituted 1-hydroxy-2-naphthanilides 15--21. Various 3-aryl-4-oxo-2,3-dihydro-1,3-naphthoxazine-2-thiones 34-43 and 3 aryl-2,4-dioxo-2,3-dihydro-1,3-naphthoxazines 44--51 have been prepared by reacting the corresonding naphthanilides with thiophosgene and ethyl chloroformate, respectively. All the compounds were tested for their cestodicidal activity against Hymenolepis nana infection in rats; 30 was found to be the most active compound of the series, showing 100% clearance of infection at a single oral dose of 7.5 mg/kg.

  DOI：

  10.1021/jm00209a020
• 作为产物：
  描述：

  2,4-二氯苯胺 、 1-羟基-2-萘甲酸 在 三氯化磷 作用下， 以 氯苯 为溶剂， 反应 0.25h， 以76%的产率得到N-(2,4-dichlorophenyl)-1-hydroxynaphthalene-2-carboxamide
  参考文献：
  名称：

  卤代1-羟基萘-2-羧苯胺类化合物对光系统II中光合电子传输的影响。

  摘要：

  制备并表征了十七种新的多卤代的1-羟基萘-2-甲酰苯胺系列。测试了所有化合物与菠菜（Spinacia oleracea L.）叶绿体中光合作用电子转运（PET）抑制相关的活性。在苯胺部分中被3,5-二氯，4-溴-3-氯，2,5-二溴和3,4,5-三氯原子取代的1-羟基-N-苯基萘-2-羧酰胺是最有效的PET抑制剂（IC50分别为5.2、6.7、7.6和8.0 µM）。这些化合物的抑制活性取决于卤素取代基的位置和类型，即取决于分子的苯胺部分的各个取代基的亲脂性和电子性质。通过荧光光谱法证明了所研究化合物与主要存在于PS II中的色素-蛋白质复合物中存在的叶绿素a和芳香族氨基酸的相互作用。可以建议将PET链中P680和质体醌QB之间在PS II受体侧出现的部分作为化合物的作用部位。讨论了构效关系。

  DOI：

  10.3390/molecules22101709

文献信息

• KISHIMOTO SATOSHI; OKUSHI TSUNEO; HIRASHIMA TSUNEAKI, SCI. AND IND., 61,(1987) N 3, 84-88
  作者：KISHIMOTO SATOSHI、 OKUSHI TSUNEO、 HIRASHIMA TSUNEAKI

  DOI：——

  日期：——
• DUBEY S. K.; SINGH A. K.; SINGH H.; SHARMA S.; IYER R. N.; KATIYAR J. C.;+, J. MED. CHEM., 1978, 21, NO 11, 1178-1181
  作者：DUBEY S. K.、 SINGH A. K.、 SINGH H.、 SHARMA S.、 IYER R. N.、 KATIYAR J. C.、+

  DOI：——

  日期：——
• Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II
  作者：Tomas Gonec、Jiri Kos、Matus Pesko、Jana Dohanosova、Michal Oravec、Tibor Liptaj、Katarina Kralova、Josef Jampilek

  DOI：10.3390/molecules22101709

  日期：——

  substituted in the anilide part by 3,5-dichloro-, 4-bromo-3-chloro-, 2,5-dibromo- and 3,4,5-trichloro atoms were the most potent PET inhibitors (IC50 = 5.2, 6.7, 7.6 and 8.0 µM, respectively). The inhibitory activity of these compounds depends on the position and the type of halogen substituents, i.e., on lipophilicity and electronic properties of individual substituents of the anilide part of the molecule

  制备并表征了十七种新的多卤代的1-羟基萘-2-甲酰苯胺系列。测试了所有化合物与菠菜（Spinacia oleracea L.）叶绿体中光合作用电子转运（PET）抑制相关的活性。在苯胺部分中被3,5-二氯，4-溴-3-氯，2,5-二溴和3,4,5-三氯原子取代的1-羟基-N-苯基萘-2-羧酰胺是最有效的PET抑制剂（IC50分别为5.2、6.7、7.6和8.0 µM）。这些化合物的抑制活性取决于卤素取代基的位置和类型，即取决于分子的苯胺部分的各个取代基的亲脂性和电子性质。通过荧光光谱法证明了所研究化合物与主要存在于PS II中的色素-蛋白质复合物中存在的叶绿素a和芳香族氨基酸的相互作用。可以建议将PET链中P680和质体醌QB之间在PS II受体侧出现的部分作为化合物的作用部位。讨论了构效关系。
• Synthesis of substituted 1-hydroxy-2-naphthanilides as potential cestodicidal agents
  作者：S. K. Dubey、A. K. Singh、H. Singh、S. Sharma、R. N. Iyer、J. C. Katiyar、P. Goel、A. B. Sen

  DOI：10.1021/jm00209a020

  日期：1978.11

  A series of substituted 1-hydroxy-2-naphthanilides 4--14 has been synthesized by treating 1-hydroxy-2-naphthoic acids 2 with substituted anilines 3. The nitronaphthanilides, on reduction and subsequent treatment with thiophosgene, gave the corresponding substituted 2-naphthanilide isothiocyanates 30--33. Substitution of the chlorine of 8 by various cyclic amines gave 3'-nitro-4'-substituted 1-hydroxy-2-naphthanilides 15--21. Various 3-aryl-4-oxo-2,3-dihydro-1,3-naphthoxazine-2-thiones 34-43 and 3 aryl-2,4-dioxo-2,3-dihydro-1,3-naphthoxazines 44--51 have been prepared by reacting the corresonding naphthanilides with thiophosgene and ethyl chloroformate, respectively. All the compounds were tested for their cestodicidal activity against Hymenolepis nana infection in rats; 30 was found to be the most active compound of the series, showing 100% clearance of infection at a single oral dose of 7.5 mg/kg.