2-hydroxy-N-(4-methoxybenzoyl)benzamide | 57135-17-8

• 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: 2-hydroxy-N-(4-methoxybenzoyl)benzamide
• 英文别名: N-(4-methoxybenzoyl)salicylamide；MP-IV-11；N-(2-hydroxy-benzoyl)-4-methoxy-benzamide；N-p-Anisoylsalicylamid
• CAS: 57135-17-8
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: BKKWERKRMVTVOS-UHFFFAOYSA-N

物化性质

• 熔点：
  197-198 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  496.9±45.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-(4-methoxybenzoyl)benzamide 在 高氯酸 作用下， 以 乙酸酐 为溶剂， 生成 2-p-Methoxyphenyl-4-oxo-4H-1,3-benzoxazinium-perchlorat
  参考文献：
  名称：

  Dorofeenko,G.N. et al., Journal of general chemistry of the USSR, 1975, vol. 45, p. 1823 - 1825

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 、 水杨酰胺 在 吡啶 作用下， 反应 2.0h， 以60%的产率得到2-hydroxy-N-(4-methoxybenzoyl)benzamide
  参考文献：
  名称：

  Synthesis of Some 2-Aryl-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones as Tools To Define the Essential Pharmacophoric Descriptors of a Benzodiazepine Receptor Ligand

  摘要：

  The synthesis and benzodiazepine receptor (BZR) affinity of some 1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones, 2-22, are reported. Compounds 2-22 are devoid of the proton donor group, which according to a BZR schematic model was one of the pharmacophoric descriptors for receptor-ligand interaction. The binding data show that 2-(2-fluorophenyl)-9-chloro-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-one (12) and some other compounds display nanomolar BZR affinity, indicating that the hydrogen donor group is not essential for the anchoring of 6,6,5-tricyclic systems to the BZR but only affects the potency of a ligand.

  DOI：

  10.1021/jm00012a020

文献信息

• Ryabukhin, Yu. I.; Faleeva, L. N.; Gorbunova, M. O., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 9, p. 1794 - 1800
  作者：Ryabukhin, Yu. I.、Faleeva, L. N.、Gorbunova, M. O.、Kovaleva, T. V.、Uflyand, I. E.、Sheinker, V. N.

  DOI：——

  日期：——
• Synthesis, Biological Evaluation, and Structure–Activity Relationships of <i>N</i>-Benzoyl-2-hydroxybenzamides as Agents Active against P. falciparum (K1 strain), Trypanosomes, and Leishmania
  作者：Jozef Stec、Qingqing Huang、Marco Pieroni、Marcel Kaiser、Alina Fomovska、Ernest Mui、William H. Witola、Samuel Bettis、Rima McLeod、Reto Brun、Alan P. Kozikowski

  DOI：10.1021/jm2015183

  日期：2012.4.12

  In our efforts to identify novel chemical scaffolds for the development of new antiprotozoal drugs, a compound library was screened against Toxoplasma gondii tachyzoites with activity discovered for N-(4-ethylbenzoyl)-2-hydroxybenzamide la against T. gondii as described elsewhere. Synthesis of a compound set was guided by T. gondii SAR with 1r found to be superior for T. gondii, also active against Thai and Sierra Leone strains of Plasmodium falciparum, and with superior ADMET properties as described elsewhere. Herein, synthesis methods and details of the chemical analysis of the compounds in this series are described. Further, this series of N-benzoyl-2-hydroxybenzamides was repurposed for testing against four other protozoan parasites: Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani, and P. falciparum (K1 isolate). Structure-activity analyses led to the identification of compounds in this set with excellent antileishmanial activity (compound 1d). Overall, compound 1r was the best and had activity 21-fold superior to that of the standard antimalarial drug chloroquine against the K1 P. falciparum isolate.
• Uflyand, I. E.; Ryabukhin, Yu. I.; Vysotskii, B. D., Koordinatsionnaya Khimiya, 1982, vol. 8, p. 501 - 506
  作者：Uflyand, I. E.、Ryabukhin, Yu. I.、Vysotskii, B. D.、Askalepov, V. N.、Kurbatov, V. P.

  DOI：——

  日期：——
• RYABUXINA O. YU.; RYABUXIN YU. I.; LUKYANOV B. S.; DOROFEENKO G. N., XIMIYA GETEROTSIKL. SOEDIN., 1979, HO 12, 1611-1616
  作者：RYABUXINA O. YU.、 RYABUXIN YU. I.、 LUKYANOV B. S.、 DOROFEENKO G. N.

  DOI：——

  日期：——
• DOROFEENKO G. N.; RYABUXIN YU. I.; MEZHERITSKIJ V. V., ZH. OBSHCH. XIMII <ZOKN-A4>, 1975, 45, HO 8, 1860-1862
  作者：DOROFEENKO G. N.、 RYABUXIN YU. I.、 MEZHERITSKIJ V. V.

  DOI：——

  日期：——