5-bromo-1-tosyl-1H-indol-3-ylboronic acid | 339540-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-bromo-1-tosyl-1H-indol-3-ylboronic acid
• 英文别名: [5-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]boronic acid
• CAS: 339540-17-9
• 化学式: C₁₅H₁₃BBrNO₄S
• 分子量: 394.054
• InChiKey: KSSVUAFLFPRHAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  23
• 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：
  87.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯-4-三氟甲基吡啶 、 5-bromo-1-tosyl-1H-indol-3-ylboronic acid 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 甲醇 、 苯 为溶剂， 反应 6.0h， 以85%的产率得到5-Bromo-1-(4-methylphenyl)sulfonyl-3-[4-(trifluoromethyl)pyridin-2-yl]indole
  参考文献：
  名称：

  Synthesis of Novel Analogues of Marine Indole Alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and Bis(indolyl)-4-trifluoromethylpyridines as Potential Anticancer Agents

  摘要：

  Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines were synthesized using Suzuki cross-coupling reaction between 2-chloro-4-trifluoromethylpyridine 9, 2,6-dichloro-4-trifluoromethylpyridine 6 or 2,6-dichloro-3-cyano-4-trifluoromethylpyridine 23 and N-tosyl-3-indolylboronic acid 10. They were evaluated for cytotoxic activity against P388 and A-549 cells with IC50 values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxylindolyl)]pyridine 18 was identified as the most potent in this series. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00070-0
• 作为产物：
  描述：

  N-tosyl-5-bromoindole 在 高氯酸 、 硼烷 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 26.25h， 生成 5-bromo-1-tosyl-1H-indol-3-ylboronic acid
  参考文献：
  名称：

  [EN] ALKYNYL ALCOHOLS AS KINASE INHIBITORS
  [FR] ALCOOLS D'ALCYNYLE UTILISÉS COMME INHIBITEURS DE KINASES

  摘要：

  选定的化合物对预防和治疗炎症和炎症性疾病，如NIK介导的疾病，具有有效性。该发明涵盖了新颖的化合物、类似物、前药及其药用可接受的盐，以及用于预防和治疗涉及炎症等疾病和其他疾病或病症的药物组合物和方法。

  公开号：

  WO2009158011A1

文献信息

• [EN] ALKYNYL ALCOHOLS AS KINASE INHIBITORS<br/>[FR] ALCOOLS D'ALCYNYLE UTILISÉS COMME INHIBITEURS DE KINASES
  申请人：AMGEN INC

  公开号：WO2009158011A1

  公开（公告）日：2009-12-30

  Selected compounds are effective for prophylaxis and treatment of inflammation and inflammatory disorders, such as NIK-mediated disorders. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, inflammation and the like.

  选定的化合物对预防和治疗炎症和炎症性疾病，如NIK介导的疾病，具有有效性。该发明涵盖了新颖的化合物、类似物、前药及其药用可接受的盐，以及用于预防和治疗涉及炎症等疾病和其他疾病或病症的药物组合物和方法。
• A highly stereoselective synthesis of indolyl N-substituted glycines
  作者：Biao Jiang、Cai-Guang Yang、Xiao-Hui Gu

  DOI：10.1016/s0040-4039(01)00229-5

  日期：2001.3

  Optically active alpha -indolyl N-substituted glycines were synthesized by reaction of an indolyl boronic acid with glyoxylic acid using chiral methylbenzylamine as the chiral auxiliary with high diastereoselectivity. The absolute configuration of the product was determined by a single-crystal X-ray analysis. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and antitumor evaluation of novel monoindolyl-4-trifluoromethylpyridines and bisindolyl-4-trifluoromethylpyridines
  作者：Biao Jiang、Xen-Nan Xiong、Cai-Guang Yang

  DOI：10.1016/s0960-894x(00)00704-6

  日期：2001.2

  A series of novel monoindolyl-4-trifluoromethylpyridines and bisindolyl-4-trifluoromethylpyridines was designed and synthesized as potential antitumor agents. They were evaluated for preliminary cytotoxic activity against P388 and A-549 cells with IC50 values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxyl-indolyl)] pyridine was identified as the most potent in this series. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of Novel Analogues of Marine Indole Alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and Bis(indolyl)-4-trifluoromethylpyridines as Potential Anticancer Agents
  作者：Wen-Nan Xiong、Cai-Guang Yang、Biao Jiang

  DOI：10.1016/s0968-0896(01)00070-0

  日期：2001.7

  Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines were synthesized using Suzuki cross-coupling reaction between 2-chloro-4-trifluoromethylpyridine 9, 2,6-dichloro-4-trifluoromethylpyridine 6 or 2,6-dichloro-3-cyano-4-trifluoromethylpyridine 23 and N-tosyl-3-indolylboronic acid 10. They were evaluated for cytotoxic activity against P388 and A-549 cells with IC50 values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxylindolyl)]pyridine 18 was identified as the most potent in this series. (C) 2001 Elsevier Science Ltd. All rights reserved.