1,1'-(1,5-dioxo-pentane)-bis[4,8,11-tris(tert-butyloxycarbonyl)-1,4,8,11-tetraazacyclotetradecane] | 203568-14-3

• 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
• 英文名称: 1,1'-(1,5-dioxo-pentane)-bis[4,8,11-tris(tert-butyloxycarbonyl)-1,4,8,11-tetraazacyclotetradecane]
• 英文别名: Tritert-butyl 11-[5-oxo-5-[4,8,11-tris(tert-butoxycarbonyl)-1,4,8,11-tetrazacyclotetradec-1-yl]pentanoyl]-1,4,8,11-tetrazacyclotetradecane-1,4,8-tricarboxylate；tritert-butyl 11-[5-oxo-5-[4,8,11-tris[(2-methylpropan-2-yl)oxycarbonyl]-1,4,8,11-tetrazacyclotetradec-1-yl]pentanoyl]-1,4,8,11-tetrazacyclotetradecane-1,4,8-tricarboxylate
• CAS: 203568-14-3
• 化学式: C₅₅H₁₀₀N₈O₁₄
• 分子量: 1097.44
• InChiKey: NJSJYYQXAVLSIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  77
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  218
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1,1'-(1,5-dioxo-pentane)-bis[4,8,11-tris(tert-butyloxycarbonyl)-1,4,8,11-tetraazacyclotetradecane] 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以97%的产率得到1,1'-(1,5-dioxo-pentane)-bis<4,8,11-trihydrochloride-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
• 作为产物：
  描述：

  1,4,8,11-四氮杂环十四烷 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 1,1'-(1,5-dioxo-pentane)-bis[4,8,11-tris(tert-butyloxycarbonyl)-1,4,8,11-tetraazacyclotetradecane]
  参考文献：
  名称：

  Tri-N-Boc-Tetraazamacrocycle-Nucleoside Conjugates: Synthesis and anti-HIV activities

  摘要：

  As far as linear N-Boc-polyamines conjugates elicited remarkable anti-HIV activity, the synthesis and anti-HIV properties of cyclic N-Boc-polyamines conjugates such as tetraazamacro-cycle-nucleoside were studied. These new conjugates include an ester linkage between the two moieties. They were synthesized using Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate coupling reagent, in the case of N-alkyl polyazamacrocycle derivatives, or through direct condensation of the acyl chloride derivative with nucleoside in the case of N-acyl polyazamacrocycle compounds, None of the new conjugates presented anti-HIV activity greater than that of the corresponding parent nucleosides.

  DOI：

  10.1080/07328319808003466

文献信息

• 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.