3,3-dibutylquinoline-2,4(1H,3H)-dione | 1228185-51-0

• 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: 3,3-dibutylquinoline-2,4(1H,3H)-dione
• 英文别名: 3,3-dibutyl-1H-quinoline-2,4-dione
• CAS: 1228185-51-0
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: CQQKNPICGRONFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯胺 在 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 3,3-dibutylquinoline-2,4(1H,3H)-dione
  参考文献：
  名称：

  水中喹啉2,4-二醇衍生物的高效化学选择性烷基化

  摘要：

  苯胺或取代的苯胺与丙二酸二乙酯的缩合反应，然后在水中的C-3进行化学选择性烷基化，从而实现喹啉2,4-二醇的各种C-3-二烷基衍生物的合成。较高的收率，易于加工和与环境兼容的条件是我们方法的主要方面。J.杂环化​​学.2011。

  DOI：

  10.1002/jhet.364

文献信息

• Synthesis and anti-HIV activity of alkylated quinoline 2,4-diols
  作者：Nafees Ahmed、Keyur G. Brahmbhatt、Sudeep Sabde、Debashis Mitra、Inder Pal Singh、Kamlesh K. Bhutani

  DOI：10.1016/j.bmc.2010.03.015

  日期：2010.4

  Naturally occurring quinolone alkaloids, buchapine (1) and compound 2 were synthesized as reported in literature and evaluated for anti-HIV potential in human CD4+ T cell line CEM-GFP, infected with HIV-1(NL4.3) virus by p24 antigen capture ELISA assay. The compounds 1 and 2 showed potent inhibitory activity with IC50 value of 2.99 and 3.80 mu M, respectively. Further, 45 alkylated derivatives of quinoline 2,4-diol were synthesized and tested for anti-HIV potential in human CD4+ T cell line CEM-GFP. Among these, 13 derivatives have shown more than 60% inhibition. We have identified three most potent inhibitors 6, 9 and 23; compound 6 was found to be more potent than lead molecule 1 with IC50 value of 2.35 mu M and had better therapeutic index (26.64) as compared to AZT (23.07). Five derivatives 7, 19a, 19d, 21 and 24 have displayed good noticeable anti-HIV activity. All active compounds showed higher CC50 values which indicate that they have better therapeutic indices. (C) 2010 Elsevier Ltd. All rights reserved.