12-(tert-butoxycarbonyl)-6,12-bis(-benzyloxy)-7-oxo-6,12-diazadodecanenitrile | 144108-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 12-(tert-butoxycarbonyl)-6,12-bis(-benzyloxy)-7-oxo-6,12-diazadodecanenitrile
• 英文别名: 12-(tert-Butoxycarbonyl)-6,12-bis(benzyloxy)-7-oxo-6,12-diazadodecanenitrile；tert-butyl N-[5-[4-cyanobutyl(phenylmethoxy)amino]-5-oxopentyl]-N-phenylmethoxycarbamate
• CAS: 144108-55-4
• 化学式: C₂₉H₃₉N₃O₅
• 分子量: 509.646
• InChiKey: FDMFXJZKKWFVKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  92.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  12-(tert-butoxycarbonyl)-6,12-bis(-benzyloxy)-7-oxo-6,12-diazadodecanenitrile 在 sodium hydroxide 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 18-(tert-butoxycarbonyl)-6,12,18-tris(benzyloxy)-7,13-dioxo-6,12,18-triazaoctadecanenitrile
  参考文献：
  名称：

  Structural alterations in desferrioxamine compatible with iron clearance in animals

  摘要：

  The design, synthesis, and biological evaluation of amideless desferrioxamine analogues are described. The design concept is predicated on the idea that a low molecular weight desferrioxamine analogue would represent a better pharmacophore from which to construct an orally effective or more efficient trihydroxamate than the parent chelator. The study demonstrates that (1) the monohydroxamate units of desferrioxamine must be linked to promote iron clearance, (2) the N-propanoyl-N-pentyl fragments of desferrioxamine can be replaced with smaller, e.g., C-5, methylene units without compromising the analogue's iron-clearing properties, and (3) a delicate balance exists between the molecule's iron-clearing efficiency and its lipophilicity.

  DOI：

  10.1021/jm00103a012
• 作为产物：
  描述：

  5-氯代戊酰氯 在 sodium hydroxide 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 12-(tert-butoxycarbonyl)-6,12-bis(-benzyloxy)-7-oxo-6,12-diazadodecanenitrile
  参考文献：
  名称：

  Structural alterations in desferrioxamine compatible with iron clearance in animals

  摘要：

  The design, synthesis, and biological evaluation of amideless desferrioxamine analogues are described. The design concept is predicated on the idea that a low molecular weight desferrioxamine analogue would represent a better pharmacophore from which to construct an orally effective or more efficient trihydroxamate than the parent chelator. The study demonstrates that (1) the monohydroxamate units of desferrioxamine must be linked to promote iron clearance, (2) the N-propanoyl-N-pentyl fragments of desferrioxamine can be replaced with smaller, e.g., C-5, methylene units without compromising the analogue's iron-clearing properties, and (3) a delicate balance exists between the molecule's iron-clearing efficiency and its lipophilicity.

  DOI：

  10.1021/jm00103a012

文献信息

• Analogs of desferrioxamine B and method for synthesis thereof
  申请人：University of Florida

  公开号：US05322961A1

  公开（公告）日：1994-06-21

  The invention relates to novel analogs of desferrioxamine, homologs thereof and methods for their synthesis.

  这项发明涉及新型去铁胺类似物、其同系物以及它们的合成方法。
• US5322961A
  申请人：——

  公开号：US5322961A

  公开（公告）日：1994-06-21
• US5364965A
  申请人：——

  公开号：US5364965A

  公开（公告）日：1994-11-15
• Structural alterations in desferrioxamine compatible with iron clearance in animals
  作者：Raymond J. Bergeron、Zhi Rong Liu、James S. McManis、Jan Wiegand

  DOI：10.1021/jm00103a012

  日期：1992.12

  The design, synthesis, and biological evaluation of amideless desferrioxamine analogues are described. The design concept is predicated on the idea that a low molecular weight desferrioxamine analogue would represent a better pharmacophore from which to construct an orally effective or more efficient trihydroxamate than the parent chelator. The study demonstrates that (1) the monohydroxamate units of desferrioxamine must be linked to promote iron clearance, (2) the N-propanoyl-N-pentyl fragments of desferrioxamine can be replaced with smaller, e.g., C-5, methylene units without compromising the analogue's iron-clearing properties, and (3) a delicate balance exists between the molecule's iron-clearing efficiency and its lipophilicity.