5-<4,8-bis(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecanyl>pentanoic ethyl ester | 203568-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂卓
• 英文名称: 5-<4,8-bis(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecanyl>pentanoic ethyl ester
• 英文别名: 5-[4,8-bis(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecyl]pentanoate ethyl ester；Ditert-butyl 4-(5-ethoxy-5-oxopentyl)-1,4,8,11-tetrazacyclotetradecane-1,11-dicarboxylate
• CAS: 203568-06-3
• 化学式: C₂₇H₅₂N₄O₆
• 分子量: 528.733
• InChiKey: IPLQLMXWKMZJIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-<4,8-bis(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecanyl>pentanoic ethyl ester 在 盐酸 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 5-[11-[5-Oxo-5-(1,4,8,11-tetrazacyclotetradec-1-yl)pentanoyl]-1,4,8,11-tetrazacyclotetradec-1-yl]pentanoic acid
  参考文献：
  名称：

  Syntheses of new unsymmetrical bispolyazamacrocycles

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)10748-1
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 5-<4,8-bis(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecanyl>pentanoic ethyl ester
  参考文献：
  名称：

  一种抗艾滋病毒药物及其制备方法

  摘要：

  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。

  公开号：

  CN105237526B
• 作为试剂：
  描述：

  1,4,8,11-四氮杂环十四烷 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 、 5-<4,8-bis(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecanyl>pentanoic ethyl ester 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 1,1'-p-xylylbis<4,8,11-tris(tert-butyloxycarbonyl)-1,4,8,11-tetraazacyclotetradecane>
  参考文献：
  名称：

  New Bicyclam−AZT Conjugates:  Design, Synthesis, Anti-HIV Evaluation, and Their Interaction with CXCR-4 Coreceptor

  摘要：

  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.

  DOI：

  10.1021/jm980358u