3-(2-nitro-phenyl)-naphtho[2,1-e][1,3]oxazine-2,4-dione | 68352-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(2-nitro-phenyl)-naphtho[2,1-e][1,3]oxazine-2,4-dione
• 英文别名: 3-(2-Nitrophenyl)benzo[h][1,3]benzoxazine-2,4-dione
• CAS: 68352-61-4
• 化学式: C₁₈H₁₀N₂O₅
• 分子量: 334.288
• InChiKey: IOABYPZFLQMOTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-hydroxy-N-(2-nitrophenyl)naphthalene-2-carboxamide 、 氯甲酸乙酯 生成 3-(2-nitro-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

文献信息

• 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：——
• 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.