5-chloro-2,3,4,9-tetrahydro-1H-β-carboline | 863110-80-9

• 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: 5-chloro-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: 5-Chloro-1H,2H,3H,4H,9H-pyrido[3,4-B]indole；5-chloro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 863110-80-9
• 化学式: C₁₁H₁₁ClN₂
• 分子量: 206.675
• InChiKey: OPKAGYFPOVUZHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  384.5±37.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-二氯苯并噻唑 、 5-chloro-2,3,4,9-tetrahydro-1H-β-carboline 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以46%的产率得到5-chloro-2-(6-chloro-1,3-benzothiazol-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Tryptoline-based benzothiazoles re-sensitize MRSA to β-lactam antibiotics

  摘要：

  Resistance-modifying agents (RMAs) offer a promising solution to combat bacterial antibiotic resistance. Here we report the discovery and structure-activity relationships of a new class of RMAs with a novel tryptoline-based benzothiazole scaffold. Our most potent compound in this series (4ad) re-sensitizes multiple MRSA strains to cephalosporins at low concentrations (2 mu g/mL) and has low mammalian cytotoxicity with a half growth inhibitory concentration (GI(50)) > 100 mu g/mL in human cervical carcinoma (HeLa) cells. In addition, the same core scaffold with different substitutions also gives good antibacterial activity against MRSA.

  DOI：

  10.1016/j.bmc.2019.115095

文献信息

• Indazole compound and pharmaceutical use thereof
  申请人：Takemiya Akihiro

  公开号：US20070173537A1

  公开（公告）日：2007-07-26

  The present invention can provide a cancer treatment drug containing, as an active ingredient, a substance selected from the group consisting of an indazole compound of the following formula (I), a pharmaceutically acceptable salt, a hydrate, a water adduct and a solvate:

  本发明可以提供一种癌症治疗药物，其包含以下公式（I）中的吲唑化合物、药用可接受盐、水合物、水加合物和溶剂化物等物质中所选的一种作为活性成分：
• US7994196B2
  申请人：——

  公开号：US7994196B2

  公开（公告）日：2011-08-09
• Tryptoline-based benzothiazoles re-sensitize MRSA to β-lactam antibiotics
  作者：Xinfeng Wang、Jinsen Chen、Wei Wang、Anna Jaunarajs、Xiang Wang

  DOI：10.1016/j.bmc.2019.115095

  日期：2019.11

  Resistance-modifying agents (RMAs) offer a promising solution to combat bacterial antibiotic resistance. Here we report the discovery and structure-activity relationships of a new class of RMAs with a novel tryptoline-based benzothiazole scaffold. Our most potent compound in this series (4ad) re-sensitizes multiple MRSA strains to cephalosporins at low concentrations (2 mu g/mL) and has low mammalian cytotoxicity with a half growth inhibitory concentration (GI(50)) > 100 mu g/mL in human cervical carcinoma (HeLa) cells. In addition, the same core scaffold with different substitutions also gives good antibacterial activity against MRSA.