N,N'-di-acridin-9-yl-butanediyldiamine | 58478-33-4

• 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: N,N'-di-acridin-9-yl-butanediyldiamine
• 英文别名: N,N'-Di-acridin-9-yl-butandiyldiamin；Acridine, 9,9'-tetramethylenediiminobis-；N,N'-di(acridin-9-yl)butane-1,4-diamine
• CAS: 58478-33-4
• 化学式: C₃₀H₂₆N₄
• 分子量: 442.563
• InChiKey: MKFRLGCMWOIRSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9-氯吖啶 、 四亚甲基二胺 在 苯酚 作用下， 生成 N,N'-di-acridin-9-yl-butanediyldiamine
  参考文献：
  名称：

  Potential antitumor agents. 44. Synthesis and antitumor activity of new classes of diacridines: importance of linker chain rigidity for DNA binding kinetics and biological activity

  摘要：

  Four classes of diacridines, joined at the 9-position by linker chains of varying length, rigidity, and polarity, were evaluated for DNA-binding properties and antitumor activity. Diacridines linked by flexible chains of varying polarity show relatively fast chromophore exchange kinetics among DNA binding sites but slower dissociation rates, suggesting the potential for considerable "creeping" of the drug along the helix, and are inactive in vivo. The exchange kinetics can be slowed dramatically by inclusion of positive charges in the side chain, but the resulting polycationic drugs are inactive in vivo, possibly due to poor distribution. Diacridines linked by a rigid, polar but neutral dicarbamoylpyrazole chain retain slow exchange kinetics, have a greatly reduced potential "creep rate", and possess good in vitro potency and significant in vivo antileukemic activity.

  DOI：

  10.1021/jm00149a005

文献信息

• Substituted bis-acridines and related compounds as CCR5 receptor ligands, anti-inflammatory agents and anti-viral agents
  申请人：SmithKline Beecham Corporation

  公开号：US20010031763A1

  公开（公告）日：2001-10-18

  This invention relates to substituted bis-acridines and related compounds which are ligands, in particular, antagonists of the CCR5 receptor. In addition, this invention relates to the treatment and prevention of disease states mediated by CCR5, including, but not limited to, asthma and atopic disorders (for example, atopic dermatitis and allergies), rheumatoid arthritis, atherosclerosis, psoriasis, autoimmune disease such as multiple sclerosis, and inflammatory bowel disease, all in mammals, by the use of substituted bis-acridines and related compounds which are CCR5 receptor antagonists. Also, since CCR5 is a co-receptor for the entry of HIV into cells, selective receptor ligands may be useful in the treatment of HIV infection.

  本发明涉及取代的双咯吩和相关化合物，它们是配体，特别是CCR5受体的拮抗剂。此外，本发明涉及通过使用取代的双咯吩和相关化合物作为CCR5受体拮抗剂来治疗和预防由CCR5介导的疾病状态，包括但不限于哮喘和过敏性疾病（例如过敏性皮炎和过敏症），类风湿性关节炎，动脉粥样硬化，牛皮癣，自身免疫疾病如多发性硬化症和炎症性肠病等哺乳动物疾病。此外，由于CCR5是HIV进入细胞的共受体，选择性受体配体可以用于治疗HIV感染。
• Ledochowski; Chimiak, Roczniki Chemii, 1959, vol. 33, p. 1207,1208
  作者：Ledochowski、Chimiak

  DOI：——

  日期：——
• DENNY, W. A.;ATWELL, G. J.;BAGULEY, B. C.;WAKALIN, L. P. G., J. MED. CHEM., 1985, 28, N 11, 1568-1574
  作者：DENNY, W. A.、ATWELL, G. J.、BAGULEY, B. C.、WAKALIN, L. P. G.

  DOI：——

  日期：——
• SUBSTITUTED BIS-ACRIDINES AND RELATED COMPOUNDS AS CCR5 RECEPTOR LIGANDS, ANTI-INFLAMMATORY AGENTS AND ANTI-VIRAL AGENTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0979078A1

  公开（公告）日：2000-02-16
• EP0979078A4
  申请人：——

  公开号：EP0979078A4

  公开（公告）日：2000-06-21