(e)-7-chloro-6-fluoro-4-hydroxy-N-(3-phenylpropylidene)quinoline-3-carboxamide | 1443747-24-7

• 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: (e)-7-chloro-6-fluoro-4-hydroxy-N-(3-phenylpropylidene)quinoline-3-carboxamide
• 英文别名: 7-chloro-6-fluoro-4-oxo-N-(3-phenylpropylidene)-1H-quinoline-3-carboxamide
• CAS: 1443747-24-7
• 化学式: C₁₉H₁₄ClFN₂O₂
• 分子量: 356.784
• InChiKey: GHWYJFOMHMHRIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二乙基[[(3-氯-4-氟苯基)氨基]亚甲基]丙二酸酯 在 氨 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (e)-7-chloro-6-fluoro-4-hydroxy-N-(3-phenylpropylidene)quinoline-3-carboxamide
  参考文献：
  名称：

  Identification and characterisation of small-molecule inhibitors of Rv3097c-encoded lipase (LipY) of Mycobacterium tuberculosis that selectively inhibit growth of bacilli in hypoxia

  摘要：

  The mycobacterial Rv3097c-encoded lipase LipY is considered as a true lipase involved in the hydrolysis of triacylglycerol stored in lipid inclusion bodies for the survival of dormant mycobacteria. To date, orlistat is the only known LipY inhibitor. In view of the important emerging role of this enzyme, a search for small-molecule inhibitors of LipY was made, leading to the identification of some new compounds (8a-8d, 8f, 8h and 8i) with potent inhibitory activities against recombinant LipY, with no cytotoxicity [50% inhibitory concentration (CC50) >= 500 mu g/mL]. The compounds 6a, 8c and 8f potently inhibited (>90%) the growth of Mycobacterium tuberculosis H(37)Rv grown under hypoxia (oxygen-depleted condition) but had no effect on aerobically grown bacilli, suggesting that these new small molecules are highly selective towards the growth inhibition of hypoxic cultures of M. tuberculosis and hence provide new leads for combating latent tuberculosis. (C) 2013 Elsevier B.V. and the International Society of Chemotherapy. All rights reserved.

  DOI：

  10.1016/j.ijantimicag.2013.03.007

文献信息

• Identification and characterisation of small-molecule inhibitors of Rv3097c-encoded lipase (LipY) of Mycobacterium tuberculosis that selectively inhibit growth of bacilli in hypoxia
  作者：Anil K. Saxena、Kuldeep K. Roy、Supriya Singh、S.P. Vishnoi、Anil Kumar、Vivek Kr. Kashyap、Laurent Kremer、Ranjana Srivastava、Brahm S. Srivastava

  DOI：10.1016/j.ijantimicag.2013.03.007

  日期：2013.7

  The mycobacterial Rv3097c-encoded lipase LipY is considered as a true lipase involved in the hydrolysis of triacylglycerol stored in lipid inclusion bodies for the survival of dormant mycobacteria. To date, orlistat is the only known LipY inhibitor. In view of the important emerging role of this enzyme, a search for small-molecule inhibitors of LipY was made, leading to the identification of some new compounds (8a-8d, 8f, 8h and 8i) with potent inhibitory activities against recombinant LipY, with no cytotoxicity [50% inhibitory concentration (CC50) >= 500 mu g/mL]. The compounds 6a, 8c and 8f potently inhibited (>90%) the growth of Mycobacterium tuberculosis H(37)Rv grown under hypoxia (oxygen-depleted condition) but had no effect on aerobically grown bacilli, suggesting that these new small molecules are highly selective towards the growth inhibition of hypoxic cultures of M. tuberculosis and hence provide new leads for combating latent tuberculosis. (C) 2013 Elsevier B.V. and the International Society of Chemotherapy. All rights reserved.