1-{3-benzyl-2-[4-fluoro-2-(1-hydroxy-ethyl)-phenoxy]-quinolin-6-yl}-3-(4-methoxy-phenyl)-urea | 1175033-29-0

• 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-{3-benzyl-2-[4-fluoro-2-(1-hydroxy-ethyl)-phenoxy]-quinolin-6-yl}-3-(4-methoxy-phenyl)-urea
• 英文别名: 1-[3-Benzyl-2-[4-fluoro-2-(1-hydroxyethyl)phenoxy]-6-quinolyl]-3-(4-methoxyphenyl)urea；1-[3-benzyl-2-[4-fluoro-2-(1-hydroxyethyl)phenoxy]quinolin-6-yl]-3-(4-methoxyphenyl)urea
• CAS: 1175033-29-0
• 化学式: C₃₂H₂₈FN₃O₄
• 分子量: 537.59
• InChiKey: VMZIXIFXRILLHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  92.7
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-[2-(2-acetyl-4-fluoro-phenoxy)-3-benzyl-quinolin-6-yl]-3-(4-methoxy-phenyl)-urea 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以40%的产率得到1-{3-benzyl-2-[4-fluoro-2-(1-hydroxy-ethyl)-phenoxy]-quinolin-6-yl}-3-(4-methoxy-phenyl)-urea
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel triazole, urea and thiourea derivatives of quinoline against Mycobacterium tuberculosis

  摘要：

  A new series of 20 quinoline derivatives possessing triazolo, ureido and thioureido substituents have been synthesized and their antimycobacterial properties have been evaluated. Compounds 10, 22 and 24 inhibited Mycobacterium tuberculosis H37Rv up to 96%, 98% and 94% respectively, at a fixed concentration of 6.25 mu g/mL. Minimum inhibitory concentration of 3.125 mu g/mL was obtained for compound 10 and 24, while for compound 22 it was 6.25 mu g/mL. Molecular docking calculations suggest critical hydrogen bonding and electrostatic interactions between polar functional groups (such as quinoline-nitrogen, urea-carbonyl and hydroxyl) of anti-mycobacterial (anti-TB) compounds and amino acids (Arg186 and Glu61) of ATP-synthase of M. tuberculosis, could be the probable reason for observed anti-mycobacterial action. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.069

文献信息

• Design, synthesis and biological evaluation of novel triazole, urea and thiourea derivatives of quinoline against Mycobacterium tuberculosis
  作者：Ram Shankar Upadhayaya、Girish M. Kulkarni、Nageswara Rao Vasireddy、Jaya Kishore Vandavasi、Shailesh S. Dixit、Vivek Sharma、Jyoti Chattopadhyaya

  DOI：10.1016/j.bmc.2009.04.069

  日期：2009.7

  A new series of 20 quinoline derivatives possessing triazolo, ureido and thioureido substituents have been synthesized and their antimycobacterial properties have been evaluated. Compounds 10, 22 and 24 inhibited Mycobacterium tuberculosis H37Rv up to 96%, 98% and 94% respectively, at a fixed concentration of 6.25 mu g/mL. Minimum inhibitory concentration of 3.125 mu g/mL was obtained for compound 10 and 24, while for compound 22 it was 6.25 mu g/mL. Molecular docking calculations suggest critical hydrogen bonding and electrostatic interactions between polar functional groups (such as quinoline-nitrogen, urea-carbonyl and hydroxyl) of anti-mycobacterial (anti-TB) compounds and amino acids (Arg186 and Glu61) of ATP-synthase of M. tuberculosis, could be the probable reason for observed anti-mycobacterial action. (C) 2009 Elsevier Ltd. All rights reserved.