(1S,4S)-(+)-2-(2,4-二氟-苄基)-2,5-二氮杂-双环[2.2.1]庚烷二(三氟甲基乙酸盐) | 845866-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1S,4S)-(+)-2-(2,4-二氟-苄基)-2,5-二氮杂-双环[2.2.1]庚烷二(三氟甲基乙酸盐)
• 英文名称: (1S,4S)-2-(4-fluorobenzyl)-2,5-diazabicyclo[2.2.1]heptane
• 英文别名: (1S,4S)-2-[(4-Fluorophenyl)methyl]-2,5-diazabicyclo[2.2.1]heptane
• CAS: 845866-69-5
• 化学式: C₁₂H₁₅FN₂
• 分子量: 206.263
• InChiKey: WOCPIKSQKAHVNP-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4S)-(+)-2-(2,4-二氟-苄基)-2,5-二氮杂-双环[2.2.1]庚烷二(三氟甲基乙酸盐) 、 1-acetyl-N-(3-chloro-4-methylphenyl)-N-(3-oxopropyl)piperidine-4-carboxamide 在 溶剂黄146 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以41%的产率得到1-acetyl-N-(3-chloro-4-methylphenyl)-N-(3-((1S,4S)-5-(4-fluorobenzyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)propyl)piperidine-4-carboxamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 2-methylpiperazine derivatives as potent CCR5 antagonists

  摘要：

  Three series of novel 2-methylpiperazine derivatives were designed and synthesized using a fragment-assembly strategy. Among them, six compounds (13, 16, 18, 22, 33, and 36) showed potent activity against CCR5 comparable to that of the positive control, maraviroc, in calcium mobilization assay. Moreover, some compounds were selected and further tested for their antiviral activity in HIV-1 single cycle assay. As a result, four compounds (13, 16, 33, and 36) showed antiviral activity at the nanomolar level. Additionally, the potent four compounds showed no cytotoxicity at a concentration of 10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.052
• 作为产物：
  描述：

  (1S)-2,5-二氮杂双环[2.2.1]庚烷 、 对氟苯甲醛 在 溶剂黄146 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以69%的产率得到(1S,4S)-(+)-2-(2,4-二氟-苄基)-2,5-二氮杂-双环[2.2.1]庚烷二(三氟甲基乙酸盐)
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 2-methylpiperazine derivatives as potent CCR5 antagonists

  摘要：

  Three series of novel 2-methylpiperazine derivatives were designed and synthesized using a fragment-assembly strategy. Among them, six compounds (13, 16, 18, 22, 33, and 36) showed potent activity against CCR5 comparable to that of the positive control, maraviroc, in calcium mobilization assay. Moreover, some compounds were selected and further tested for their antiviral activity in HIV-1 single cycle assay. As a result, four compounds (13, 16, 33, and 36) showed antiviral activity at the nanomolar level. Additionally, the potent four compounds showed no cytotoxicity at a concentration of 10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.052

文献信息

• Design, synthesis, and biological evaluation of novel 2-methylpiperazine derivatives as potent CCR5 antagonists
  作者：Suwen Hu、Zhilong Wang、Tingjun Hou、Xiaodong Ma、Jing Li、Tao Liu、Xin Xie、Yongzhou Hu

  DOI：10.1016/j.bmc.2014.12.052

  日期：2015.3

  Three series of novel 2-methylpiperazine derivatives were designed and synthesized using a fragment-assembly strategy. Among them, six compounds (13, 16, 18, 22, 33, and 36) showed potent activity against CCR5 comparable to that of the positive control, maraviroc, in calcium mobilization assay. Moreover, some compounds were selected and further tested for their antiviral activity in HIV-1 single cycle assay. As a result, four compounds (13, 16, 33, and 36) showed antiviral activity at the nanomolar level. Additionally, the potent four compounds showed no cytotoxicity at a concentration of 10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.