4--N-<(tert-butyloxy)carbonyl>phenethylamine | 144226-17-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4--N-<(tert-butyloxy)carbonyl>phenethylamine
• 英文别名: tert-butyl N-[2-[4-[bis(2-hydroxyethyl)amino]phenyl]ethyl]carbamate
• CAS: 144226-17-5
• 化学式: C₁₇H₂₈N₂O₄
• 分子量: 324.42
• InChiKey: YRKMUYMUZYCJIO-UHFFFAOYSA-N

物化性质

• 沸点：
  524.1±50.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  82
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4--N-<(tert-butyloxy)carbonyl>phenethylamine 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 N-<4-phenethyl>-N^α,N^δ-bis(benzyloxycarbonyl)-N^α-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate
  参考文献：
  名称：

  Synthesis and evaluation of novel spermidine derivatives as targeted cancer chemotherapeutic agents

  摘要：

  The utility of the spermidine moiety as the homing device for the selective delivery of chemotherapeutic and diagnostic agents into cancer cells was explored. Two spermidine analogs containing a cytotoxic agent were synthesized, N-[3,4-bis(benzyloxy)phenethyl]-N(alpha)-(3-amino-propyl)-L-ornithinamide trihydrochloride, 1a and N-[4-[bis(2-chloroethyl)amino]phenethyl]-N(alpha)-(3-aminopropyl)-L-ornithinamide tetrahydrochloride, lb. These compounds were prepared from the fully protected spermidine molecule with a carboxyl group side chain, 8. The ability of the polyamine cytotoxic agents to inhibit B16-BL6 melanoma cell growth in culture was examined. The effects of pretreatment with DFMO on the activity of the synthesized compounds was also studied. The IC50 values of compounds la and lb were on the same order of magnitude as the control compounds, N-acetyldopamine and chlorambucil, respectively. The inhibitory activities of compounds la and lb were not enhanced by pretreatment with DFMO, suggesting that depletion of intracellular polyamines did not enhance the activity of these compounds.

  DOI：

  10.1021/jm00101a002
• 作为产物：
  描述：

  碳酸二叔丁酯 在 palladium on activated charcoal 3 A molecular sieve 、 氢气 、 sodium cyanoborohydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 2.0h， 生成 4--N-<(tert-butyloxy)carbonyl>phenethylamine
  参考文献：
  名称：

  Synthesis and evaluation of novel spermidine derivatives as targeted cancer chemotherapeutic agents

  摘要：

  The utility of the spermidine moiety as the homing device for the selective delivery of chemotherapeutic and diagnostic agents into cancer cells was explored. Two spermidine analogs containing a cytotoxic agent were synthesized, N-[3,4-bis(benzyloxy)phenethyl]-N(alpha)-(3-amino-propyl)-L-ornithinamide trihydrochloride, 1a and N-[4-[bis(2-chloroethyl)amino]phenethyl]-N(alpha)-(3-aminopropyl)-L-ornithinamide tetrahydrochloride, lb. These compounds were prepared from the fully protected spermidine molecule with a carboxyl group side chain, 8. The ability of the polyamine cytotoxic agents to inhibit B16-BL6 melanoma cell growth in culture was examined. The effects of pretreatment with DFMO on the activity of the synthesized compounds was also studied. The IC50 values of compounds la and lb were on the same order of magnitude as the control compounds, N-acetyldopamine and chlorambucil, respectively. The inhibitory activities of compounds la and lb were not enhanced by pretreatment with DFMO, suggesting that depletion of intracellular polyamines did not enhance the activity of these compounds.

  DOI：

  10.1021/jm00101a002

文献信息

• Synthesis and evaluation of novel spermidine derivatives as targeted cancer chemotherapeutic agents
  作者：Peter A. Stark、Brian D. Thrall、Gary G. Meadows、Mahmoud M. Abdel-Monem

  DOI：10.1021/jm00101a002

  日期：1992.11

  The utility of the spermidine moiety as the homing device for the selective delivery of chemotherapeutic and diagnostic agents into cancer cells was explored. Two spermidine analogs containing a cytotoxic agent were synthesized, N-[3,4-bis(benzyloxy)phenethyl]-N(alpha)-(3-amino-propyl)-L-ornithinamide trihydrochloride, 1a and N-[4-[bis(2-chloroethyl)amino]phenethyl]-N(alpha)-(3-aminopropyl)-L-ornithinamide tetrahydrochloride, lb. These compounds were prepared from the fully protected spermidine molecule with a carboxyl group side chain, 8. The ability of the polyamine cytotoxic agents to inhibit B16-BL6 melanoma cell growth in culture was examined. The effects of pretreatment with DFMO on the activity of the synthesized compounds was also studied. The IC50 values of compounds la and lb were on the same order of magnitude as the control compounds, N-acetyldopamine and chlorambucil, respectively. The inhibitory activities of compounds la and lb were not enhanced by pretreatment with DFMO, suggesting that depletion of intracellular polyamines did not enhance the activity of these compounds.