(4-tert-butoxycarbonylamino-butyl)-(4-{[4-({4-[tert-butoxycarbonyl-(4-tert-butoxycarbonylamino-butyl)amino]butylamino}methyl)naphthalen-1-ylmethyl]amino}butyl)carbamic acid tert-butyl ester | 1016243-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4-tert-butoxycarbonylamino-butyl)-(4-{[4-({4-[tert-butoxycarbonyl-(4-tert-butoxycarbonylamino-butyl)amino]butylamino}methyl)naphthalen-1-ylmethyl]amino}butyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-N-[4-[[4-[[4-[(2-methylpropan-2-yl)oxycarbonyl-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]amino]butylamino]methyl]naphthalen-1-yl]methylamino]butyl]carbamate
• CAS: 1016243-14-3
• 化学式: C₄₈H₈₂N₆O₈
• 分子量: 871.214
• InChiKey: YXAPXUZEWJOQNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  62
• 可旋转键数：
  32
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (4-tert-butoxycarbonylamino-butyl)-(4-{[4-({4-[tert-butoxycarbonyl-(4-tert-butoxycarbonylamino-butyl)amino]butylamino}methyl)naphthalen-1-ylmethyl]amino}butyl)carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙醇 为溶剂， 以94%的产率得到N-(4-amino-butyl)-N'-(4-{[4-(4-aminobutylamino)butylamino]methyl}naphthalen-1-ylmethyl)butane-1,4-diamine hexahydrochloride
  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：

  1,4-萘二羧醛 、 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60%的产率得到(4-tert-butoxycarbonylamino-butyl)-(4-{[4-({4-[tert-butoxycarbonyl-(4-tert-butoxycarbonylamino-butyl)amino]butylamino}methyl)naphthalen-1-ylmethyl]amino}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

• POLYAMINE TRANSPORTER SELECTIVE COMPOUNDS AS ANTI CANCER AGENTS
  申请人：Phanstiel, IV Otto

  公开号：US20140057989A1

  公开（公告）日：2014-02-27

  Several aromatic hydrocarbons di-substituted with a polyamine are described according to formulas selected from compounds 4, 7, 10, 15 and pharmaceutically acceptable salts thereof. The novel dimeric polyamines of the present invention demonstrate enhanced penetration into cells having an upregulated polyamine transport system, such as various types of cancer cells. The disclosed aromatic polyamine dimers provide highly efficient drugs for targeting cancer cells with active polyamine transporters.
• Polyamine Transporter Selective Compounds as Anti-Cancer Agents
  申请人：Phanstiel, IV Otto

  公开号：US20160075633A1

  公开（公告）日：2016-03-17

  Several aromatic hydrocarbons di-substituted with a polyamine are described according to formulas selected from compounds 4, 7, 10, 15 and pharmaceutically acceptable salts thereof. The novel dimeric polyamines of the present invention demonstrate enhanced penetration into cells having an upregulated polyamine transport system, such as various types of cancer cells. The disclosed aromatic polyamine dimers provide highly efficient drugs for targeting cancer cells with active polyamine transporters.
• US8497398B1
  申请人：——

  公开号：US8497398B1

  公开（公告）日：2013-07-30
• US9150495B2
  申请人：——

  公开号：US9150495B2

  公开（公告）日：2015-10-06
• US9598351B2
  申请人：——

  公开号：US9598351B2

  公开（公告）日：2017-03-21