N^α-tert-butyloxycarbonyl-N-(5,11-dimethyl-5H-indolo[2,3-b]quinolin-2-yl)-L-histidylamide | 1606990-07-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N^α-tert-butyloxycarbonyl-N-(5,11-dimethyl-5H-indolo[2,3-b]quinolin-2-yl)-L-histidylamide
• CAS: 1606990-07-1
• 化学式: C₂₈H₃₀N₆O₃
• 分子量: 498.585
• InChiKey: HKYHRUKNHZWOQX-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  113.93
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N^α-tert-butyloxycarbonyl-N-(5,11-dimethyl-5H-indolo[2,3-b]quinolin-2-yl)-L-histidylamide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到N-(5,11-dimethyl-5H-indolo[2,3-b]quinolin-2-yl)-Lhistidylamidetetrahydrochloride
  参考文献：
  名称：

  Searching for new derivatives of neocryptolepine: Synthesis, antiproliferative, antimicrobial and antifungal activities

  摘要：

  A series of novel amino acid and dipeptide derivatives of neocryptolepine were synthesized and tested for their antimicrobial, antifungal and antiproliferative activity in vitro against cancer cell lines (KB, A549, MCF-7, LoVo) and normal mice fibroblast cells (BALB/3T3). Biological evaluation revealed that almost all of the new compounds displayed high antiproliferative activity against the tested cells and moderate to potent antibacterial activities. Interestingly, these compounds were active against Candida albicans biofilms at doses significantly lower than those required against free-floating planktonic fungal cells. The most promising compounds are derivatives with glycine and c-proline as a substituent both at 2 and at 9 position of 5H-indolo[2,3-b]quinoline. In general, these new compounds (2a, 3a, 6a and 7a) showed the highest dual action against cancer lines and infectious pathogenic microbes in vitro. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.060
• 作为产物：
  描述：

  5,11-dimethyl-5H-indolo[2,3-b]quinolin-2-ylamine 、 N-Boc-L-组氨酸 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以65%的产率得到N^α-tert-butyloxycarbonyl-N-(5,11-dimethyl-5H-indolo[2,3-b]quinolin-2-yl)-L-histidylamide
  参考文献：
  名称：

  Searching for new derivatives of neocryptolepine: Synthesis, antiproliferative, antimicrobial and antifungal activities

  摘要：

  A series of novel amino acid and dipeptide derivatives of neocryptolepine were synthesized and tested for their antimicrobial, antifungal and antiproliferative activity in vitro against cancer cell lines (KB, A549, MCF-7, LoVo) and normal mice fibroblast cells (BALB/3T3). Biological evaluation revealed that almost all of the new compounds displayed high antiproliferative activity against the tested cells and moderate to potent antibacterial activities. Interestingly, these compounds were active against Candida albicans biofilms at doses significantly lower than those required against free-floating planktonic fungal cells. The most promising compounds are derivatives with glycine and c-proline as a substituent both at 2 and at 9 position of 5H-indolo[2,3-b]quinoline. In general, these new compounds (2a, 3a, 6a and 7a) showed the highest dual action against cancer lines and infectious pathogenic microbes in vitro. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.060