phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-3-yl)methanone | 1344109-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-3-yl)methanone
• 英文别名: [1-(1-hydroxy-3H-2,1-benzoxaborol-6-yl)pyrrol-3-yl]-phenylmethanone
• CAS: 1344109-55-2
• 化学式: C₁₈H₁₄BNO₃
• 分子量: 303.125
• InChiKey: AIKSCBCGFCBKBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-3-yl)methanone 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 以28.8%的产率得到6-(3-benzylpyrrol-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
• 作为产物：
  描述：

  2-溴-4-硝基苯甲酸 在 锂硼氢 、 正丁基锂 、 氯化亚砜 、 tin(II) chloride dihdyrate 、 硼酸三异丙酯 、 四氯化锡 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 32.5h， 生成 phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-2-yl)methanone 、 phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-3-yl)methanone
  参考文献：
  名称：

  无水氯化锡催化新型吡咯并苯并氧杂硼骨架骨架的合成及其通过Friedel-Crafts反应的衍生化

  摘要：

  摘要从2-溴-1-经六步合成了一种新型的吡咯并苯并恶唑硼酸酯6-（吡咯-1-基）-1,3-二氢-1-羟基-2,1-苯并恶硼酸酯，其总收率为27％。以甲基-4-硝基苯为原料。它的衍生化是通过无水锡氯化物与各种酰基氯催化的Friedel-Crafts反应实现的，从而以3-酰基-1-苯基吡咯为主要产物。

  DOI：

  10.1016/j.cclet.2011.06.005

文献信息

• Synthesis of a novel pyrrolo-benzoxaborole scaffold and its derivatization via Friedel–Crafts reaction catalyzed by anhydrous stannic chloride
  作者：Pu Hua Wu、Qing Qing Meng、Hu Chen Zhou

  DOI：10.1016/j.cclet.2011.06.005

  日期：2011.12

  was synthesized with 27% overall yield over six steps from 2-bromo-1-methyl-4-nitrobenzene as starting material. Its derivatization was achieved via Friedel–Crafts reaction catalyzed by anhydrous stannic chloride with various acyl chlorides giving 3-acyl-1-phenylpyrroles as the main products.

  摘要从2-溴-1-经六步合成了一种新型的吡咯并苯并恶唑硼酸酯6-（吡咯-1-基）-1,3-二氢-1-羟基-2,1-苯并恶硼酸酯，其总收率为27％。以甲基-4-硝基苯为原料。它的衍生化是通过无水锡氯化物与各种酰基氯催化的Friedel-Crafts反应实现的，从而以3-酰基-1-苯基吡咯为主要产物。
• 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.