4-(allyloxy(pyridin-4-yl)methyl)-6-bromo-2-methylquinoline | 1222417-40-4

• 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: 4-(allyloxy(pyridin-4-yl)methyl)-6-bromo-2-methylquinoline
• 英文别名: 6-Bromo-2-methyl-4-[prop-2-enoxy(pyridin-4-yl)methyl]quinoline
• CAS: 1222417-40-4
• 化学式: C₁₉H₁₇BrN₂O
• 分子量: 369.261
• InChiKey: MWWJUVIIBZRPEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(allyloxy(pyridin-4-yl)methyl)-6-bromo-2-methylquinoline 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以45%的产率得到1-bromo-3-((6-bromo-2-methylquinolin-4-yl)(pyridin-4-yl)methoxy)propan-2-ol
  参考文献：
  名称：

  Novel quinoline and naphthalene derivatives as potent antimycobacterial agents

  摘要：

  We have designed and synthesized both the quinoline and naphthalene based molecules influenced by the unique structural make-up of mefloquine and TMC207, respectively. These compounds were evaluated for their anti-mycobacterial activity against drug sensitive Mycobacterium tuberculosis H37Rv in vitro at single-dose concentration (6.25 mu g/mL). The compounds 22,23, 26 and 27 inhibited the growth of M. tuberculosis H37Rv 99%, 90%, 98% and 91% respectively. Minimum inhibitory concentration of compounds 22, 23, 26 and 27 was found to be 6.25 mu g/mL.. Our molecular modeling and docking studies of designed compounds showed hydrogen bonding with Glu-61, Tyr-64 and Asn-190 amino acid residues at the putative binding site of ATP synthase, these interactions were coherent as shown by Mefloquine and TMC207, where hydrogen bonding was found with Tyr-64 and Glu-61 respectively. SAR analysis indicates importance of hydroxyl group and nature of substituents on piperazinyl-phenyl ring was critical in dictating the biological activity of newly synthesized compounds. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.024
• 作为产物：
  描述：

  (6-bromo-2-methylquinolin-4-yl)(pyridin-4-yl)methanol 、 3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以70%的产率得到4-(allyloxy(pyridin-4-yl)methyl)-6-bromo-2-methylquinoline
  参考文献：
  名称：

  Novel quinoline and naphthalene derivatives as potent antimycobacterial agents

  摘要：

  We have designed and synthesized both the quinoline and naphthalene based molecules influenced by the unique structural make-up of mefloquine and TMC207, respectively. These compounds were evaluated for their anti-mycobacterial activity against drug sensitive Mycobacterium tuberculosis H37Rv in vitro at single-dose concentration (6.25 mu g/mL). The compounds 22,23, 26 and 27 inhibited the growth of M. tuberculosis H37Rv 99%, 90%, 98% and 91% respectively. Minimum inhibitory concentration of compounds 22, 23, 26 and 27 was found to be 6.25 mu g/mL.. Our molecular modeling and docking studies of designed compounds showed hydrogen bonding with Glu-61, Tyr-64 and Asn-190 amino acid residues at the putative binding site of ATP synthase, these interactions were coherent as shown by Mefloquine and TMC207, where hydrogen bonding was found with Tyr-64 and Glu-61 respectively. SAR analysis indicates importance of hydroxyl group and nature of substituents on piperazinyl-phenyl ring was critical in dictating the biological activity of newly synthesized compounds. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.024