bisnaphthalimidopropylspermidine trihydrobromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: bisnaphthalimidopropylspermidine trihydrobromide
• 英文别名: BNIPSpd；Bisnaphthalimidopropyl spermidine trihydrobromide；2-[3-[4-[3-[3-(1,3-dioxobenzo[de]isoquinolin-2-yl)propylamino]propylamino]butylamino]propyl]benzo[de]isoquinoline-1,3-dione;hydrobromide
• 化学式: 3BrH*C₃₇H₄₁N₅O₄
• 分子量: 862.499
• InChiKey: GPNBTIDIHYXYID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  亚精胺 在 吡啶 、 氢溴酸 、 caesium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 bisnaphthalimidopropylspermidine trihydrobromide
  参考文献：
  名称：

  The synthesis and in vitro cytotoxic studies of novel bis-naphthalimidopropyl polyamine derivatives

  摘要：

  Bis-naphthalimidopropyl putrescine (BNIPPut), spermidine (BNIPSpd), spermine (BNIPSpm) and oxa-putrescine (BNIPOPut) were synthesised and their growth-inhibitory properties characterised. All these compounds except for BNIPOPut, showed high in vitro cytotoxic activity (with mean GI(50) values between 0.5 and 8.45 mu M) and selectivity against cancer cells derived from nine different human tumours. The increased content of nitrogen atoms in the linker chain of BNIPSpd and BNIPSpm significantly improved their aqueous dissolution properties with a marginal decrease in their cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00293-6

文献信息

• The synthesis and the in vitro cytotoxicity studies of bisnaphthalimidopropyl polyamine derivatives against colon cancer cells and parasite Leishmania infantum
  作者：João Oliveira、Lynda Ralton、Joana Tavares、Anabela Codeiro-da-Silva、Charles S. Bestwick、Anne McPherson、Paul Kong Thoo Lin

  DOI：10.1016/j.bmc.2006.09.031

  日期：2007.1.1

  Bisnaphthalimidopropyl derivatives (BNIPSpd, BNIPDaoct, BNIPDanon, BNIPDadec, BNIPDpta and BNIPDeta) were synthesised in yields ranging from 50% to 70% and their cytotoxicity against colon cancer cells (Caco-2) and the parasite Leishmania infantum determined using the MTT assay. Cytotoxicity within Caco-2 cells was manifested with IC50 values between 0.3 and 22 mu M. Compounds with the central longer alkyl chains exhibited the highest cytotoxicity. Against L. infantum, IC50 values were encompassed within a narrower concentration range of 0.47-1.54 mu M. In the parasites, the presence of nitrogen in the central chain and the length of the central alkyl chains did not especially enhance cytotoxicity. This may be due to the way these compounds are transported in the cells. (c) 2006 Elsevier Ltd. All rights reserved.