(1RS,9RS,10SR)-(Z)-9-acetoxy-11-(benzylcarbamoyl)-11-azabicyclo[8.2.0]dodec-5-ene-3,7-diyn-12-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (1RS,9RS,10SR)-(Z)-9-acetoxy-11-(benzylcarbamoyl)-11-azabicyclo[8.2.0]dodec-5-ene-3,7-diyn-12-one
• 英文别名: [(1R,5Z,9R,10S)-11-(benzylcarbamoyl)-12-oxo-11-azabicyclo[8.2.0]dodec-5-en-3,7-diyn-9-yl] acetate
• 化学式: C₂₁H₁₈N₂O₄
• 分子量: 362.385
• InChiKey: AODBKUNLJLLZHM-HFZBTABESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1RS,9RS,10SR)-(Z)-9-acetoxy-11-(tert-butoxycarbonyl)-11-azabicyclo[8.2.0]dodec-5-ene-3,7-diyn-12-one 、 异氰酸苄酯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(1RS,9RS,10SR)-(Z)-9-acetoxy-11-(benzylcarbamoyl)-11-azabicyclo[8.2.0]dodec-5-ene-3,7-diyn-12-one
  参考文献：
  名称：

  Synthesis and DNA-cleaving activity of lactenediynes conjugated with DNA-complexing moieties

  摘要：

  Lactenediynes are compounds characterized by the fusion of a beta-lactam with a cyclodeca-3-ene-1,5-diyne. In this work the most promising members of this family have been activated by attaching a carbalkoxy or a carbamoyl group to the azetidinone nitrogen, and conjugated to various DNA-complexing moieties, either acting by intercalation or through groove binding. These conjugated artificial enediynes have been demonstrated to possess in vitro ability to produce single and double strand cleavage of plasmid DNA. As potency and capacity to induce double cut, they rank among the best simple enediyne analogues ever prepared. A thorough investigation was carried out in order to develop the best suited linkers for assembling these conjugates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.022

文献信息

• Synthesis and DNA-cleaving activity of lactenediynes conjugated with DNA-complexing moieties
  作者：Luca Banfi、Andrea Basso、Elisabetta Bevilacqua、Valentina Gandolfo、Giuseppe Giannini、Giuseppe Guanti、Loana Musso、Monica Paravidino、Renata Riva

  DOI：10.1016/j.bmc.2008.02.022

  日期：2008.4.1

  Lactenediynes are compounds characterized by the fusion of a beta-lactam with a cyclodeca-3-ene-1,5-diyne. In this work the most promising members of this family have been activated by attaching a carbalkoxy or a carbamoyl group to the azetidinone nitrogen, and conjugated to various DNA-complexing moieties, either acting by intercalation or through groove binding. These conjugated artificial enediynes have been demonstrated to possess in vitro ability to produce single and double strand cleavage of plasmid DNA. As potency and capacity to induce double cut, they rank among the best simple enediyne analogues ever prepared. A thorough investigation was carried out in order to develop the best suited linkers for assembling these conjugates. (C) 2008 Elsevier Ltd. All rights reserved.