1-methyl-2-pentadecyl-4(1H)-quinolone | 59443-03-7

• 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-methyl-2-pentadecyl-4(1H)-quinolone
• 英文别名: 1-methyl-2-pentadecyl-1H-quinolin-4-one；1-Methyl-2-pentadecyl-4(1H)-chinolon；1-methyl-2-pentadecylquinolin-4-one
• CAS: 59443-03-7
• 化学式: C₂₅H₃₉NO
• 分子量: 369.591
• InChiKey: YOXIQBPUPGISEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (5-羧基戊基)三苯基溴化磷 在 10% palladium on activated carbon 、 氢气 、 sodium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正庚烷 、 乙基苯 为溶剂， 反应 33.5h， 生成 1-methyl-2-pentadecyl-4(1H)-quinolone
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones

  摘要：

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.060

文献信息

• Quinolone alkaloids from Evodia rutaecarpa
  作者：Yuan-Qing Tang、Xiao-Zhang Feng、Liang Huang

  DOI：10.1016/0031-9422(96)00304-4

  日期：1996.10

  Five new quinolone alkaloids were isolated from the fruits of Evodia rutaecarpa, together with seven known ones. Their structures were determined on the basis of spectral data and chemical reactions.

  从吴茱萸果实中分离出五种新型喹诺酮类生物碱，以及七种已知的喹诺酮类生物碱。它们的结构是根据光谱数据和化学反应确定的。
• Synthesis of Unnatural 2-Substituted Quinolones and 1,3-Diketones by a Member of Type III Polyketide Synthases from <i>Huperzia serrata</i>
  作者：Juan Wang、Xiao-Hui Wang、Xiao Liu、Jun Li、Xiao-Ping Shi、Yue-Lin Song、Ke-Wu Zeng、Le Zhang、Peng-Fei Tu、She-Po Shi

  DOI：10.1021/acs.orglett.6b01501

  日期：2016.8.5

  A curcuminoids, benzalacetone-, and quinolone-producing type III polyketide synthase (HsPKS3) from Huperzia serrata uniquely catalyzes the formation of unnatural 2-substituted quinolones and 1,3-diketones via head-to-head condensation of two completely different substrates. The broad range of substrate tolerance of HsPKS3 facilitates accessing structurally diverse 2-substituted quinolones and 1,3-diketones.
• Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones
  作者：Abraham A. Wube、Antje Hüfner、Christina Thomaschitz、Martina Blunder、Manfred Kollroser、Rudolf Bauer、Franz Bucar

  DOI：10.1016/j.bmc.2010.10.060

  日期：2011.1

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.