[(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl 3-nitrobenzoate | 1430722-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl 3-nitrobenzoate
• CAS: 1430722-50-1
• 化学式: C₂₃H₂₁N₃O₄
• 分子量: 403.437
• InChiKey: OSLUJIDAMFAPGR-SPLOXXLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  间硝基苯甲酰氯 、 麦角醇 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl 3-nitrobenzoate
  参考文献：
  名称：

  Antibacterial and Synergy of Clavine Alkaloid Lysergol and its Derivatives Against Nalidixic Acid-ResistantEscherichia coli

  摘要：

  Antibacterial activity of lysergol (1) and its semi‐synthetic derivatives (2–14) and their synergy with the conventional antibiotic nalidixic acid (NA) against nalidixic acid‐sensitive (NASEC) and nalidixic acid‐resistant (NAREC) strains of Escherichia coli were evaluated. Lysergol (1) and derivatives (2–14) did not possess antibacterial activity of their own, but in combination, they significantly reduced the minimum inhibitory concentration (MIC) of NA. All the derivatives showed two‐ to eightfold reduction in the MIC of NA against NAREC and NASEC. Further, lysergol (1) and its derivatives 10 and 11 brought down eightfold reductions in the MIC of tetracycline (TET) against multidrug‐resistant clinical isolate of E. coli (MDREC). Treatment of these strains with the combinations of antibiotics and lysergol and its derivatives 10 and 11 (at reduced concentrations) significantly decreased the viability of cells. In an another observation, lysergol and its derivatives 10 and 11 inhibited ATP‐dependent efflux pumps, which was evident by ATPase inhibition and down‐regulation of multidrug ABC transporter ATP‐binding protein (yojI) gene. These results may be of great help in antibacterial drug development from a very common, inexpensive, and non‐toxic natural product.

  DOI：

  10.1111/cbdd.12103

文献信息

• Antibacterial and Synergy of Clavine Alkaloid Lysergol and its Derivatives Against Nalidixic Acid-Resistant<i>Escherichia coli</i>
  作者：Anupam Maurya、Gaurav R. Dwivedi、Mahendra P. Darokar、Santosh K. Srivastava

  DOI：10.1111/cbdd.12103

  日期：2013.4

  Antibacterial activity of lysergol (1) and its semi‐synthetic derivatives (2–14) and their synergy with the conventional antibiotic nalidixic acid (NA) against nalidixic acid‐sensitive (NASEC) and nalidixic acid‐resistant (NAREC) strains of Escherichia coli were evaluated. Lysergol (1) and derivatives (2–14) did not possess antibacterial activity of their own, but in combination, they significantly reduced the minimum inhibitory concentration (MIC) of NA. All the derivatives showed two‐ to eightfold reduction in the MIC of NA against NAREC and NASEC. Further, lysergol (1) and its derivatives 10 and 11 brought down eightfold reductions in the MIC of tetracycline (TET) against multidrug‐resistant clinical isolate of E. coli (MDREC). Treatment of these strains with the combinations of antibiotics and lysergol and its derivatives 10 and 11 (at reduced concentrations) significantly decreased the viability of cells. In an another observation, lysergol and its derivatives 10 and 11 inhibited ATP‐dependent efflux pumps, which was evident by ATPase inhibition and down‐regulation of multidrug ABC transporter ATP‐binding protein (yojI) gene. These results may be of great help in antibacterial drug development from a very common, inexpensive, and non‐toxic natural product.