普乐沙福杂质27 | 170161-28-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 普乐沙福杂质27
• 英文名称: 4,8-bis-(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecane
• 英文别名: Ditert-butyl 1,4,8,11-tetrazacyclotetradecane-1,11-dicarboxylate
• CAS: 170161-28-1
• 化学式: C₂₀H₄₀N₄O₄
• 分子量: 400.562
• InChiKey: AGLFKGXNUQNTBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  83.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  普乐沙福杂质27 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 5,5'-(1,4,8,11-tetraazacyclotetradecane-1,11-diyl)bis(methylene)diquinolin-8-ol
  参考文献：
  名称：

  Synthesis and anti-HIV properties of new hydroxyquinoline–polyamine conjugates on cells infected by HIV-1 LAV and HIV-1 BaL viral strains

  摘要：

  To find new derivatives that block different virus strains entry in cells bearing specific surface receptors represent an interesting challenge for medicinal chemists. Here, we report the synthesis and the anti-HIV properties of a new series of analogues based on the introduction of quinoline moiety on various polyamine backbones, including polyazamacrocycles. Three compounds 7, 8, and 10 of this series were found active on PBMCs cells infected by HIV-1 LAV or by HIV-1 BaL, in contrast the well-known reference compound 1a (AMD 3100) was found only active on HIV-1 LAV strain.

  DOI：

  10.1016/j.bmcl.2006.08.114
• 作为产物：
  描述：

  1,4,8,11-四氮杂环十四烷 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 普乐沙福杂质27
  参考文献：
  名称：

  摘要：

  The selective use of the tert-butoxycarbonyl protecting group has enabled efficient syntheses of the tri-linked cyclam derivatives (6)-(8). Using a related protecting group strategy, a series of related single-ring, N-benzylated cyclam derivatives (1)-(4) has also been prepared.

  DOI：

  10.1071/ch01070

文献信息

• 1,4,8,11-Tetraazabicyclo[9.3.1]pentadecanes: Synthesis and Use of a New Strategy for the Selective <i>cis</i>-N⁴,N⁸-Difunctionalization of Cyclam Derivatives
  作者：Roger Guilard、Alla Bessmertnykh、Irina Beletskaya

  DOI：10.1055/s-1997-975

  日期：1997.10

  A new efficient route to derivatives of 1,4,8,11-tetraazabicyclo[9.3.1]pentadecane 2 and their use in a procedure of selective N4,N8-difunctionalization of cyclam is reported.

  报道了一种新的高效合成1,4,8,11-四氮杂双环[9.3.1]十五烷衍生物2的路线及其在选择性N4,N8双功能化环胺的程序中的应用。
• 一种抗艾滋病毒药物及其制备方法
  申请人：朱靖华

  公开号：CN105237526B

  公开（公告）日：2018-01-23

  一种抗艾滋病毒药物及其制备方法，本发明公开了一种雷特格韦衍生物酯及其制备方法，该雷特格韦衍生物酯的化学名称是：N‑(2’‑(4’‑(4’‑氟苄基氨基甲酰基)‑1’‑甲基‑6’‑氧代‑1’,6’‑二氢嘧啶‑2’‑基)‑5’‑甲基‑1’,3’,4’‑恶二唑‑2’‑甲酰胺‑5’‑氧‑5‑[1,4,8,11‑四氮杂环十四烷基]甲基}苯基)‑1,4,8,11‑四氮杂环十四烷基]}‑R‑羧酸酯。其显示了比雷特格韦明显较高的活性（EC50）和选择性指数（SI=EC50/CC50），并显著增加了溶解性。
• New Bicyclam−AZT Conjugates:  Design, Synthesis, Anti-HIV Evaluation, and Their Interaction with CXCR-4 Coreceptor
  作者：Jean Dessolin、Pascale Galea、Patrick Vlieghe、Jean-Claude Chermann、Jean-Louis Kraus

  DOI：10.1021/jm980358u

  日期：1999.1.1

  We report the synthesis of mono- and bis-tetraazamacrocycle-AZT conjugates. All new compounds were screened for their ability to inhibit HIV-1 replication in MT4 cell line and were compared to AZT alone. It appears that N-protected covalent prodrugs are equipotent to AZT as inhibitor of HIV replication, while N-deprotected analogues exhibit both higher activity and selectivity against HIV-infected cells. The most active antiviral compounds 27, 28, 34, and 35 were then tested for their binding capability to CXCR-4 receptor. N-Boc analogues 27 and 34 were only weakly effective; in contrast, N-deprotected conjugates 28 and 35 were antagonists to 12G5 mAb binding until 0.05 and 5 mu g/mL, respectively. The stability of compound 28 in human plasma was evaluated, and half-life was found to be approximately 8 h in the described conditions. All these results seem to demonstrate the confidence of our prodrug approach, with analogue 28 emerging as the best candidate as lead compound in HIV-1 polytherapy perspective.
• Syntheses of new unsymmetrical bispolyazamacrocycles
  作者：J. Dessolin、G. Quéléver、M. Camplo、J.L. Kraus

  DOI：10.1016/s0040-4039(97)10748-1

  日期：1998.2

  We report the synthesis of an original unsymmetrical bismacrocycle bearing a carboxylic side-arm. Two different synthetic pathways were investigated, both involving a Schotten-Baumann like reaction. The first route allowed us to obtain a mixture of compounds whilst the second one was direct and non-ambiguous. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Characterization and application of a new diprotected cyclam: a novel two-step synthesis of linked tetraazamacrocycles
  作者：Bernard Boitrel、Bruno Andrioletti、Mohammed Lachkar、Roger Guilard

  DOI：10.1016/0040-4039(95)00931-2

  日期：1995.7