(E)-5-[2-(4-methoxyphenyl)ethenyl]benzo[1,2-c]-1,2,5-oxadiazole N¹-oxide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-5-[2-(4-methoxyphenyl)ethenyl]benzo[1,2-c]-1,2,5-oxadiazole N¹-oxide
• 英文别名: 5-[(E)-2-(4-methoxyphenyl)ethenyl]-1-oxido-2,1,3-benzoxadiazol-1-ium
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: FUFNMQMEVXWCNS-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基溴苄 在 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (E)-5-[2-(4-methoxyphenyl)ethenyl]benzo[1,2-c]-1,2,5-oxadiazole N¹-oxide
  参考文献：
  名称：

  Second generation of 5-ethenylbenzofuroxan derivatives as inhibitors of Trypanosoma cruzi growth: Synthesis, biological evaluation, and structure–activity relationships

  摘要：

  In vitro growth inhibitory activity of 21 new 5-ethenylbenzofuroxan derivatives against the protozoan parasite Trypanosoma cruzi, the causative agent of American trypanosomiasis, was studied. The designed compounds possess the previously described exigencies for optimal anti-parasite activity, the 5-ethenylbenzofuroxanyl moiety with different substituents. The synthetic key for preparing the derivatives was the Wittig procedure, that when 5-formylbenzofuroxan was used as the electrophile the corresponding deoxygenated products were marginally generated. Four of the new derivatives displayed remarkable in vitro activities against the epimastigote form of three strains of T cruzi, Tulahuen 2, CL Brener, and Y. While the three deoxygenated analogues biologically assayed resulted inactives. Unspecific cytotoxicity was evaluated using human macrophages and active derivatives were not toxic at a concentration at least 13 times that Of its IC50 against T cruzi (CL Brener strain). From the preliminary structure-activity relationship studies lipophilicity and electronic requirements were found relevant to anti-T cruzi activity. Active compounds are more lipophilic than inactive ones and it was also identified that an optimum value of R Swain-Lupton's descriptor is required for optimal activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.009

文献信息

• Second generation of 5-ethenylbenzofuroxan derivatives as inhibitors of Trypanosoma cruzi growth: Synthesis, biological evaluation, and structure–activity relationships
  作者：Williams Porcal、Paola Hernández、Gabriela Aguirre、Lucía Boiani、Mariana Boiani、Alicia Merlino、Ana Ferreira、Rossanna Di Maio、Ana Castro、Mercedes González、Hugo Cerecetto

  DOI：10.1016/j.bmc.2007.01.009

  日期：2007.4

  In vitro growth inhibitory activity of 21 new 5-ethenylbenzofuroxan derivatives against the protozoan parasite Trypanosoma cruzi, the causative agent of American trypanosomiasis, was studied. The designed compounds possess the previously described exigencies for optimal anti-parasite activity, the 5-ethenylbenzofuroxanyl moiety with different substituents. The synthetic key for preparing the derivatives was the Wittig procedure, that when 5-formylbenzofuroxan was used as the electrophile the corresponding deoxygenated products were marginally generated. Four of the new derivatives displayed remarkable in vitro activities against the epimastigote form of three strains of T cruzi, Tulahuen 2, CL Brener, and Y. While the three deoxygenated analogues biologically assayed resulted inactives. Unspecific cytotoxicity was evaluated using human macrophages and active derivatives were not toxic at a concentration at least 13 times that Of its IC50 against T cruzi (CL Brener strain). From the preliminary structure-activity relationship studies lipophilicity and electronic requirements were found relevant to anti-T cruzi activity. Active compounds are more lipophilic than inactive ones and it was also identified that an optimum value of R Swain-Lupton's descriptor is required for optimal activity. (c) 2007 Elsevier Ltd. All rights reserved.