2-[3-(4-ethylphenyl)-[1,2,4]oxadiazol-5-yl]phenol | 1369525-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[3-(4-ethylphenyl)-[1,2,4]oxadiazol-5-yl]phenol
• 英文别名: QQ-428；2-[3-(4-Ethylphenyl)-1,2,4-oxadiazol-5-yl]phenol；2-[3-(4-ethylphenyl)-1,2,4-oxadiazol-5-yl]phenol
• CAS: 1369525-73-4
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: OSJCWPANCTYEQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  水杨酰胺 在 吡啶 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成 2-[3-(4-ethylphenyl)-[1,2,4]oxadiazol-5-yl]phenol
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Structure–Activity Relationships of N-Benzoyl-2-hydroxybenzamides as Agents Active against P. falciparum (K1 strain), Trypanosomes, and Leishmania

  摘要：

  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.

  DOI：

  10.1021/jm2015183

文献信息

• 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.