6-(3-(4-methoxyphenylsulfinyl)indol-1-yl)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole | 1309068-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-(3-(4-methoxyphenylsulfinyl)indol-1-yl)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole
• 英文别名: 6-[3-(4-methoxyphenylsulfinyl)indol-1-yl]-1,3-dihydro-1-hydroxy-2,1-benzoxaborole；1-(1-hydroxy-3H-2,1-benzoxaborol-6-yl)-3-(4-methoxyphenyl)sulfinylindole
• CAS: 1309068-63-0
• 化学式: C₂₂H₁₈BNO₄S
• 分子量: 403.266
• InChiKey: PPTHNOBJIUZFDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  79.9
• 氢给体数：
  1
• 氢受体数：
  5

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 、 双氧水 、 碘 、 caesium carbonate 、 对甲苯磺酸 、 溶剂黄146 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 12.25h， 生成 6-(3-(4-methoxyphenylsulfinyl)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

• [EN] BORON-CONTAINING SMALL MOLECULES AS ANTIHELMINTH AGENTS<br/>[FR] PETITES MOLÉCULES CONTENANT DU BORE EN TANT QU'AGENTS ANTIHELMINTHES
  申请人：ANACOR PHARMACEUTICALS INC

  公开号：WO2011063293A1

  公开（公告）日：2011-05-26

  This invention provides, among other things, novel compounds useful for treating helminth infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.

  这项发明提供了用于治疗蠕虫感染的新型化合物，包含这些化合物的药物组合物，以及这些化合物与至少一种额外治疗有效药剂的组合。
• 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.