(4-{4-[bis-(2-chloro-ethyl)amino]benzylamino}butyl)-(4-tert-butoxycarbonylamino-butyl)carbamic acid tert-butyl ester | 1016243-17-6

• 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: (4-{4-[bis-(2-chloro-ethyl)amino]benzylamino}butyl)-(4-tert-butoxycarbonylamino-butyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[4-[[4-[bis(2-chloroethyl)amino]phenyl]methylamino]butyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]carbamate
• CAS: 1016243-17-6
• 化学式: C₂₉H₅₀Cl₂N₄O₄
• 分子量: 589.646
• InChiKey: XWQPSJCCPOVMCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  39
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  83.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-{4-[bis-(2-chloro-ethyl)amino]benzylamino}butyl)-(4-tert-butoxycarbonylamino-butyl)carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙醇 为溶剂， 以96%的产率得到N-(4-amino-butyl)-N'-{4-[bis-(2-chloro-ethyl)amino]benzyl}butane-1,4-diamine trihydrochloride
  参考文献：
  名称：

  A Comparison of Chloroambucil- and Xylene-Containing Polyamines Leads to Improved Ligands for Accessing the Polyamine Transport System

  摘要：

  Several disubstituted arylene- and chloroambucil-polyamine conjugates were synthesized and evaluated for their ability to target cells via their polyamine transport system (PAT). As compared to the monosubstituted analogues, the disubstituted arylene systems were superior PAT targeting agents. Using a Chinese hamster ovary (CHO) cell line (PAT active) and its CHO-MG mutant (PAT inactive), the series was screened for their PAT targeting ability. The data were expressed as a CHOMG/CHO IC50 ratio. Indeed, the disubstituted systems gave high IC50 ratios (e.g., ratio > 2000), which indicated high selectivity for the PAT. The chloroambucil adducts were less toxic than the corresponding arylmethyl compounds. In this regard, having the proper recognition element (i.e., homospermidine) and cytotoxic "cargo" were deemed paramount for successful drug delivery via the PAT.

  DOI：

  10.1021/jm070794t
• 作为产物：
  描述：

  4-[双-(2-氯乙基)氨基]苯甲醛 、 tert-butyl (4-aminobutyl)(4-((tert-butoxycarbonyl)amino)butyl)carbamate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以91%的产率得到(4-{4-[bis-(2-chloro-ethyl)amino]benzylamino}butyl)-(4-tert-butoxycarbonylamino-butyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  A Comparison of Chloroambucil- and Xylene-Containing Polyamines Leads to Improved Ligands for Accessing the Polyamine Transport System

  摘要：

  Several disubstituted arylene- and chloroambucil-polyamine conjugates were synthesized and evaluated for their ability to target cells via their polyamine transport system (PAT). As compared to the monosubstituted analogues, the disubstituted arylene systems were superior PAT targeting agents. Using a Chinese hamster ovary (CHO) cell line (PAT active) and its CHO-MG mutant (PAT inactive), the series was screened for their PAT targeting ability. The data were expressed as a CHOMG/CHO IC50 ratio. Indeed, the disubstituted systems gave high IC50 ratios (e.g., ratio > 2000), which indicated high selectivity for the PAT. The chloroambucil adducts were less toxic than the corresponding arylmethyl compounds. In this regard, having the proper recognition element (i.e., homospermidine) and cytotoxic "cargo" were deemed paramount for successful drug delivery via the PAT.

  DOI：

  10.1021/jm070794t

文献信息

• A Comparison of Chloroambucil- and Xylene-Containing Polyamines Leads to Improved Ligands for Accessing the Polyamine Transport System
  作者：Navneet Kaur、Jean-Guy Delcros、Jon Imran、Annette Khaled、Mounir Chehtane、Nuska Tschammer、Bénédicte Martin、Otto Phanstiel

  DOI：10.1021/jm070794t

  日期：2008.3.13

  Several disubstituted arylene- and chloroambucil-polyamine conjugates were synthesized and evaluated for their ability to target cells via their polyamine transport system (PAT). As compared to the monosubstituted analogues, the disubstituted arylene systems were superior PAT targeting agents. Using a Chinese hamster ovary (CHO) cell line (PAT active) and its CHO-MG mutant (PAT inactive), the series was screened for their PAT targeting ability. The data were expressed as a CHOMG/CHO IC50 ratio. Indeed, the disubstituted systems gave high IC50 ratios (e.g., ratio > 2000), which indicated high selectivity for the PAT. The chloroambucil adducts were less toxic than the corresponding arylmethyl compounds. In this regard, having the proper recognition element (i.e., homospermidine) and cytotoxic "cargo" were deemed paramount for successful drug delivery via the PAT.