6-(3-(2-hydroxyphenylsulfanyl)indol-1-yl)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole | 1309068-71-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(3-(2-hydroxyphenylsulfanyl)indol-1-yl)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole
• 英文别名: 6-[3-(2-hydroxyphenylsulfanyl)indol-1-yl]-1,3-dihydro-1-hydroxy-2,1-benzoxaborole；2-[1-(1-hydroxy-3H-2,1-benzoxaborol-6-yl)indol-3-yl]sulfanylphenol
• CAS: 1309068-71-0
• 化学式: C₂₁H₁₆BNO₃S
• 分子量: 373.24
• InChiKey: OSEPOZAGFMKPGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-4-氟苯甲醛 在 盐酸 、 sodium tetrahydroborate 、 正丁基锂 、 碘 、 caesium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.25h， 生成 6-(3-(2-hydroxyphenylsulfanyl)indol-1-yl)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole
  参考文献：
  名称：

  Novel pyrrolobenzoxaboroles: Design, synthesis, and biological evaluation against Trypanosoma brucei

  摘要：

  Human African trypanosomiasis is a fatal parasitic infection caused by the protozoan Trypanosoma brucei. The development of novel antitrypanosomal agents is urgently needed. Here we report the synthesis and structure-activity relationship of a new class of benzoxaboroles as antitrypanosomal agents. These compounds showed antiparasitic IC50 values ranging from 4.02 to 0.03 mu g/mL and satisfactory cytotoxicity profile. Three of the lead compounds were demonstrated to cure the parasitic infection in a murine acute infection model. The structure activity relationship of the pyrrolobenzoxaboroles are also discussed. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.079

文献信息

• Novel pyrrolobenzoxaboroles: Design, synthesis, and biological evaluation against Trypanosoma brucei
  作者：Puhua Wu、Jiong Zhang、Qingqing Meng、Bakela Nare、Robert T. Jacobs、Huchen Zhou

  DOI：10.1016/j.ejmech.2014.04.079

  日期：2014.6

  Human African trypanosomiasis is a fatal parasitic infection caused by the protozoan Trypanosoma brucei. The development of novel antitrypanosomal agents is urgently needed. Here we report the synthesis and structure-activity relationship of a new class of benzoxaboroles as antitrypanosomal agents. These compounds showed antiparasitic IC50 values ranging from 4.02 to 0.03 mu g/mL and satisfactory cytotoxicity profile. Three of the lead compounds were demonstrated to cure the parasitic infection in a murine acute infection model. The structure activity relationship of the pyrrolobenzoxaboroles are also discussed. (C) 2014 Elsevier Masson SAS. All rights reserved.