3,5,7-tri[(4'-methylpiperazin-1'-yl)methyl]tropolone | 1242270-34-3

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 3,5,7-tri[(4'-methylpiperazin-1'-yl)methyl]tropolone
• 英文别名: 2-Hydroxy-3,5,7-tris[(4-methylpiperazin-1-yl)methyl]cyclohepta-2,4,6-trien-1-one
• CAS: 1242270-34-3
• 化学式: C₂₅H₄₂N₆O₂
• 分子量: 458.647
• InChiKey: VJRSBPNHUAADOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 聚合甲醛 、 环庚三烯酚酮 以 水 为溶剂， 以72%的产率得到3,5,7-tri[(4'-methylpiperazin-1'-yl)methyl]tropolone
  参考文献：
  名称：

  Studies on the anti-hepatitis C virus activity of newly synthesized tropolone derivatives: Identification of NS3 helicase inhibitors that specifically inhibit subgenomic HCV replication

  摘要：

  We synthesized new tropolone derivatives substituted with cyclic amines: piperidine, piperazine or pyrrolidine. The most active anti-helicase compound (IC50 = 3.4 mu M), 3,5,7-tri[(4'-methylpiperazin-1'-yl)methyl]tropolone (2), inhibited RNA replication by 50% at 46.9 mu M (EC50) and exhibited the lowest cytotoxicity (CC50) >1 mM resulting in a selectivity index (SI = CC50/EC50) >21. The most efficient replication inhibitor, 3,5,7-tri[(4'-methylpiperidin-1'-yl)methyl]tropolone (6), inhibited RNA replication with an EC50 of 32.0 mu M and a SI value of 17.4, whereas 3,5,7-tri[(3'-methylpiperidin-1'-yl)methyl] tropolone (7) exhibited a slightly lower activity with an EC50 of 35.6 mu M and a SI of 9.8. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.066

文献信息

• [EN] HCV HELICASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE L'HÉLICASE DU VHC ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV KANSAS

  公开号：WO2013036749A1

  公开（公告）日：2013-03-14

  The present invention discloses thioflavine S and primuline derivatives which inhibit hepatitis C virus helicase and protease activity. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are useful as antiviral agents. The present invention further relates to pharmaceutical compositions containing the aforementioned compounds and methods of treating an HCV infection.

  本发明揭示了硫黄素S和原黄素衍生物，可抑制丙型肝炎病毒的解旋酶和蛋白酶活性。因此，本发明的化合物干扰丙型肝炎病毒的生命周期，并可用作抗病毒剂。本发明还涉及含有上述化合物的药物组合物和治疗HCV感染的方法。
• HCV Helicase Inhibitors and Methods of Use Thereof
  申请人：Aube Jeffrey

  公开号：US20140227225A1

  公开（公告）日：2014-08-14

  The present invention discloses thioflavine S and primuline derivatives which inhibit hepatitis C virus helicase and protease activity. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are useful as antiviral agents. The present invention further relates to pharmaceutical compositions containing the aforementioned compounds and methods of treating an HCV infection.

  本发明揭示了硫黄荧光素S和初黄素衍生物，其抑制丙型肝炎病毒的解旋酶和蛋白酶活性。因此，本发明的化合物干扰了丙型肝炎病毒的生命周期，并可用作抗病毒剂。本发明还涉及含有上述化合物的制药组合物和治疗HCV感染的方法。
• US9464064B2
  申请人：——

  公开号：US9464064B2

  公开（公告）日：2016-10-11
• Studies on the anti-hepatitis C virus activity of newly synthesized tropolone derivatives: Identification of NS3 helicase inhibitors that specifically inhibit subgenomic HCV replication
  作者：Andżelika Najda-Bernatowicz、Mariusz Krawczyk、Anna Stankiewicz-Drogoń、Maria Bretner、Anna M. Boguszewska-Chachulska

  DOI：10.1016/j.bmc.2010.05.066

  日期：2010.7

  We synthesized new tropolone derivatives substituted with cyclic amines: piperidine, piperazine or pyrrolidine. The most active anti-helicase compound (IC50 = 3.4 mu M), 3,5,7-tri[(4'-methylpiperazin-1'-yl)methyl]tropolone (2), inhibited RNA replication by 50% at 46.9 mu M (EC50) and exhibited the lowest cytotoxicity (CC50) >1 mM resulting in a selectivity index (SI = CC50/EC50) >21. The most efficient replication inhibitor, 3,5,7-tri[(4'-methylpiperidin-1'-yl)methyl]tropolone (6), inhibited RNA replication with an EC50 of 32.0 mu M and a SI value of 17.4, whereas 3,5,7-tri[(3'-methylpiperidin-1'-yl)methyl] tropolone (7) exhibited a slightly lower activity with an EC50 of 35.6 mu M and a SI of 9.8. (C) 2010 Elsevier Ltd. All rights reserved.