1-(naphthalen-1-yl(phenyl)methoxy)-3-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)propan-2-ol | 1222417-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(naphthalen-1-yl(phenyl)methoxy)-3-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)propan-2-ol
• 英文别名: 1-[1-Naphthyl(phenyl)methoxy]-3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propan-2-ol；1-[naphthalen-1-yl(phenyl)methoxy]-3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propan-2-ol
• CAS: 1222417-60-8
• 化学式: C₃₁H₃₁F₃N₂O₂
• 分子量: 520.595
• InChiKey: VKEKQOWZBFVSMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-((naphthalen-1-yl(phenyl)methoxy)methyl)oxirane 、 1-(3-三氟甲基苯基)哌嗪 以 异丙醇 为溶剂， 反应 16.0h， 以31%的产率得到1-(naphthalen-1-yl(phenyl)methoxy)-3-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)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

文献信息

• Novel quinoline and naphthalene derivatives as potent antimycobacterial agents
  作者：Ram Shankar Upadhayaya、Jaya Kishore Vandavasi、Ramakant A. Kardile、Santosh V. Lahore、Shailesh S. Dixit、Hemantkumar S. Deokar、Popat D. Shinde、Manash P. Sarmah、Jyoti Chattopadhyaya

  DOI：10.1016/j.ejmech.2010.01.024

  日期：2010.5

  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.