1-propyl-2-[(1E)-decenyl]-4-(1H)-quinolone | 1310368-23-0

• 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: 1-propyl-2-[(1E)-decenyl]-4-(1H)-quinolone
• 英文别名: 2-[(E)-dec-1-enyl]-1-propyl-quinolin-4-one；2-[(E)-dec-1-enyl]-1-propylquinolin-4-one
• CAS: 1310368-23-0
• 化学式: C₂₂H₃₁NO
• 分子量: 325.494
• InChiKey: UTPYVFMRQRZNOH-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-propylisatoic anhydride 、 十二碳-3-烯-2-酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到1-propyl-2-[(1E)-decenyl]-4-(1H)-quinolone
  参考文献：
  名称：

  Synthesis of N-substituted 2-[(1E)-alkenyl]-4-(1H)-quinolone derivatives as antimycobacterial agents against non-tubercular mycobacteria

  摘要：

  In an effort to improve biological activities and to examine antimycobacterial-lipophilicity relationships of 2-[(1E)-alkenyl)]-4-(1H)-quinolones, we have synthesized a series of 30 quinolones by introducing several alkyl groups, an alkenyl and an alkynyl group at N-1. All synthetic compounds were first tested in vitro against Mycobacterium smegmatis and the most active compounds (MIC values similar to 3.0-7.0 mu M) were further examined against three other rapidly growing strains of mycobacteria using a microtiter broth dilution assay. The Clog P values of the synthetic compounds were calculated to provide an estimate of their lipophilicity. Compounds 18e, 19a and 19b displayed the most potent inhibitory effect against M. smegmatis mc(2)155 with an MIC value of similar to 1.5 mu M, which was twenty fold and thirteen fold more potent than isoniazid and ethambutol, respectively. On the other hand, compounds 17e, 18e and 19a were most active against Mycobacterium fortuitum and Mycobacterium phlei with an MIC value of similar to 3.0 mu M. In the human diploid embryonic lung cell line MRC-5 cytotoxicity assay, the derivatives showed moderate to strong cytotoxic activity. Although the antimycobacterial activity of our synthetic compounds could not be correlated with the calculated log P values, an increase in lipophilicity enhances the antimycobacterial activity and C-13-C-15 total chain length at positions 1 and 2 is required to achieve optimal inhibitory effect against the test strains. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.062

文献信息

• Synthesis of N-substituted 2-[(1E)-alkenyl]-4-(1H)-quinolone derivatives as antimycobacterial agents against non-tubercular mycobacteria
  作者：Abraham A. Wube、Franz Bucar、Christina Hochfellner、Martina Blunder、Rudolf Bauer、Antje Hüfner

  DOI：10.1016/j.ejmech.2011.02.062

  日期：2011.6

  In an effort to improve biological activities and to examine antimycobacterial-lipophilicity relationships of 2-[(1E)-alkenyl)]-4-(1H)-quinolones, we have synthesized a series of 30 quinolones by introducing several alkyl groups, an alkenyl and an alkynyl group at N-1. All synthetic compounds were first tested in vitro against Mycobacterium smegmatis and the most active compounds (MIC values similar to 3.0-7.0 mu M) were further examined against three other rapidly growing strains of mycobacteria using a microtiter broth dilution assay. The Clog P values of the synthetic compounds were calculated to provide an estimate of their lipophilicity. Compounds 18e, 19a and 19b displayed the most potent inhibitory effect against M. smegmatis mc(2)155 with an MIC value of similar to 1.5 mu M, which was twenty fold and thirteen fold more potent than isoniazid and ethambutol, respectively. On the other hand, compounds 17e, 18e and 19a were most active against Mycobacterium fortuitum and Mycobacterium phlei with an MIC value of similar to 3.0 mu M. In the human diploid embryonic lung cell line MRC-5 cytotoxicity assay, the derivatives showed moderate to strong cytotoxic activity. Although the antimycobacterial activity of our synthetic compounds could not be correlated with the calculated log P values, an increase in lipophilicity enhances the antimycobacterial activity and C-13-C-15 total chain length at positions 1 and 2 is required to achieve optimal inhibitory effect against the test strains. (C) 2011 Elsevier Masson SAS. All rights reserved.