(1R,2R,4R)-1,7,7-trimethyl-N-(4-(4-((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylamino)phenoxy)phenyl)bicyclo[2.2.1]heptan-2-amine | 1594978-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,4R)-1,7,7-trimethyl-N-(4-(4-((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylamino)phenoxy)phenyl)bicyclo[2.2.1]heptan-2-amine
• 英文别名: (1R,2R,4R)-1,7,7-trimethyl-N-[4-[4-[[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]amino]phenoxy]phenyl]bicyclo[2.2.1]heptan-2-amine
• CAS: 1594978-48-9
• 化学式: C₃₂H₄₄N₂O
• 分子量: 472.714
• InChiKey: GCAGXFFXEXLMPN-ORCXNALQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  33.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-N-((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)-4-(4-((E)-((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)phenoxy)aniline 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以34%的产率得到(1R,2R,4R)-1,7,7-trimethyl-N-(4-(4-((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylamino)phenoxy)phenyl)bicyclo[2.2.1]heptan-2-amine
  参考文献：
  名称：

  Camphor-based symmetric diimines as inhibitors of influenza virus reproduction

  摘要：

  Influenza is a continuing world-wide public health problem that causes significant morbidity and mortality during seasonal epidemics and sporadic pandemics. The purpose of the study was synthesis and investigation of antiviral activity of camphor-based symmetric diimines and diamines. A set of C2-symmetric nitrogen-containing camphor derivatives have been synthesized. The antiviral activity of these compounds was studied against rimantadine- and amantadine-resistant influenza virus A/California/7/09 (H1N1)pdm09 in MDCK cells. The highest efficacy in virus inhibiting was shown for compounds 2a-e with cage moieties bound by aliphatic linkers. The therapeutic index (selectivity index) for 2b exceeded that for reference compounds amantadine, deitiforin and rimantadine almost 10-fold. As shown by structure-activity analysis, the length of the linker has a dramatic effect on the toxicity of compounds. Compound 2e with -C12H24-linker exhibited the lowest toxicity (CTD50 = 2216 mu M). Derivatives of camphor, therefore, can be considered as prospective antiinfluenza compounds active against influenza viruses resistant to adamantane-based drugs. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.038

文献信息

• Camphor-based symmetric diimines as inhibitors of influenza virus reproduction
  作者：Anastasiya S. Sokolova、Оlga I. Yarovaya、Dina V. Korchagina、Vladimir V. Zarubaev、Tatiana S. Tretiak、Pavel M. Anfimov、Oleg I. Kiselev、Nariman F. Salakhutdinov

  DOI：10.1016/j.bmc.2014.02.038

  日期：2014.4

  Influenza is a continuing world-wide public health problem that causes significant morbidity and mortality during seasonal epidemics and sporadic pandemics. The purpose of the study was synthesis and investigation of antiviral activity of camphor-based symmetric diimines and diamines. A set of C2-symmetric nitrogen-containing camphor derivatives have been synthesized. The antiviral activity of these compounds was studied against rimantadine- and amantadine-resistant influenza virus A/California/7/09 (H1N1)pdm09 in MDCK cells. The highest efficacy in virus inhibiting was shown for compounds 2a-e with cage moieties bound by aliphatic linkers. The therapeutic index (selectivity index) for 2b exceeded that for reference compounds amantadine, deitiforin and rimantadine almost 10-fold. As shown by structure-activity analysis, the length of the linker has a dramatic effect on the toxicity of compounds. Compound 2e with -C12H24-linker exhibited the lowest toxicity (CTD50 = 2216 mu M). Derivatives of camphor, therefore, can be considered as prospective antiinfluenza compounds active against influenza viruses resistant to adamantane-based drugs. (C) 2014 Elsevier Ltd. All rights reserved.