tert-butyl N-[6-(9-acridinylamino)hexyl]carbamate | 811800-78-9

• 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: tert-butyl N-[6-(9-acridinylamino)hexyl]carbamate
• 英文别名: tert-butyl N-[6-(acridin-9-ylamino)hexyl]carbamate
• CAS: 811800-78-9
• 化学式: C₂₄H₃₁N₃O₂
• 分子量: 393.529
• InChiKey: IFLMVTPSMLSYNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[6-(9-acridinylamino)hexyl]carbamate 在 N-甲基吗啉 、 盐酸 、 氯甲酸异丁酯 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 ethyl 2-((2-{[6-(9-acridinylamino)hexyl]amino}-2-oxoethyl){2-[di-(2-ethoxy-2-oxoethyl)amino]ethyl}amino) acetate
  参考文献：
  名称：

  Synthesis of pathogen inactivating nucleic acid intercalators

  摘要：

  A series of antiviral compounds consisting of an intercalating acridine derived part, a spacer region and a reactive EDTA-derived conjugate was synthesized in an easy sequence starting from 1,omega-alkyldiamines. As shown in model screenings, in the presence of ascorbic acid the Fe-complexes of these compounds reduced the phage-titer of MS2-phages by several logarithmic decades. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.07.011
• 作为产物：
  描述：

  1,6-己二胺 在 苯酚 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 tert-butyl N-[6-(9-acridinylamino)hexyl]carbamate
  参考文献：
  名称：

  Synthesis of pathogen inactivating nucleic acid intercalators

  摘要：

  A series of antiviral compounds consisting of an intercalating acridine derived part, a spacer region and a reactive EDTA-derived conjugate was synthesized in an easy sequence starting from 1,omega-alkyldiamines. As shown in model screenings, in the presence of ascorbic acid the Fe-complexes of these compounds reduced the phage-titer of MS2-phages by several logarithmic decades. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.07.011

文献信息

• 9-Acridinyl and 2-methoxy-6-chloro-9-acridinyl derivatives of aliphatic di-, tri-, and tetraamines. Chemistry, cytostatic activity, and schistosomicidal activity
  作者：John B. Hansen、Eyvind Langvad、Flemming Frandsen、Ole Buchardt

  DOI：10.1021/jm00364a028

  日期：1983.10

  9-acridinyl derivatives of 1,6-hexanediamine, 1,8-octanediamine, bis(3-aminopropyl)amine, N,N'-bis(3-amino-propyl)piperazine, and N-ethyl-1,6-hexanediamine in the form of their hydrochlorides were prepared in high yields and converted into potential hetero bis DNA intercalating diacridines. The corresponding potential homo bis DNA intercalating reagents were prepared by heating the above amines with

  1,6-己二胺，1,8-辛二胺，双（3-氨基丙基）胺，N，N'-双（3-氨基丙基）哌嗪和N-乙基-1,6-己二胺的9-ac啶基衍生物以高收率制备它们的盐酸盐形式的草甘膦，并将其转化成潜在的插入双异核苷的杂双DNA。通过将上述胺与9-氯ac啶一起加热来制备相应的潜在的均双bis DNA插入试剂。检查了idine啶的化学稳定性。已经确定了它们在体外对Cloudman黑色素瘤细胞的细胞抑制活性。对于三胺和四胺的cr啶衍生物观察到最强的细胞抑制活性。发现所选的a啶和二cr啶衍生物在小鼠中对曼氏血吸虫的血吸虫杀伤作用微不足道。S.
• Antimalarial acridines: Synthesis, in vitro activity against P. falciparum and interaction with hematin
  作者：Lucie Guetzoyan、Xiao-Min Yu、Florence Ramiandrasoa、Stéphanie Pethe、Christophe Rogier、Bruno Pradines、Thierry Cresteil、Martine Perrée-Fauvet、Jean-Pierre Mahy

  DOI：10.1016/j.bmc.2009.10.005

  日期：2009.12

  A series of acridine derivatives were synthesised and their in vitro antimalarial activity was evaluated against one chloroquine-susceptible strain (3D7) and three chloroquine-resistant strains (W2, Bre1 and FCR3) of Plasmodium falciparum. Structure–activity relationship showed that two positives charges as well as 6-chloro and 2-methoxy substituents on the acridine ring were required to exert a good

  合成了一系列of啶衍生物，并评估了它们对恶性疟原虫的一个对氯喹敏感的菌株（3D7）和三个对氯喹耐药的菌株（W2，Bre1和FCR3）的体外抗疟活性。结构-活性关系表明，required啶环上需要两个正电荷以及6-氯和2-甲氧基取代基才能发挥良好的抗疟活性。具有这些特性的最佳化合物抑制氯喹敏感的菌株的生长，其IC 50  ⩽0.07μM，接近氯喹本身，以及与IC三个抗氯喹株比氯喹更好的50 ⩽0.3μM。这些a啶衍生物抑制了β-血红素的形成，表明它们像CQ一样作用于血红素结晶过程。最后，还对人KB细胞进行了体外细胞毒性评估，结果表明，其中的9-（6-氨基乙基氨基）-6-氯-2-甲氧基ac啶二氯化物1在体外具有良好的选择性抗疟疾活性，相对于CQ易感菌株上具有哺乳动物细胞，并且对其他菌株具有有希望的选择性。
• Synthesis of pathogen inactivating nucleic acid intercalators
  作者：René Csuk、Alexander Barthel、Thorsten Brezesinski、Christian Raschke

  DOI：10.1016/j.ejmech.2004.07.011

  日期：2004.11

  A series of antiviral compounds consisting of an intercalating acridine derived part, a spacer region and a reactive EDTA-derived conjugate was synthesized in an easy sequence starting from 1,omega-alkyldiamines. As shown in model screenings, in the presence of ascorbic acid the Fe-complexes of these compounds reduced the phage-titer of MS2-phages by several logarithmic decades. (C) 2004 Elsevier SAS. All rights reserved.