N-<3-(4-methylbenzenesulfonoxy)propyl>naphthalimide | 59529-41-8

• 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: N-<3-(4-methylbenzenesulfonoxy)propyl>naphthalimide
• 英文别名: 3-tosyloxypropylnaphthalimide；3-(1,3-Dioxobenzo[de]isoquinolin-2-yl)propyl 4-methylbenzenesulfonate
• CAS: 59529-41-8
• 化学式: C₂₂H₁₉NO₅S
• 分子量: 409.463
• InChiKey: DVOTWFTXTONYLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  623.7±38.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-<3-(4-methylbenzenesulfonoxy)propyl>naphthalimide 在 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 20.0h， 生成 2-[3-[2-[3-(1,3-Dioxobenzo[de]isoquinolin-2-yl)propylamino]oxyethoxyamino]propyl]benzo[de]isoquinoline-1,3-dione;hydrobromide
  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
• 作为产物：
  描述：

  1,8-萘二甲酸酐 在 吡啶 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 5.0h， 生成 N-<3-(4-methylbenzenesulfonoxy)propyl>naphthalimide
  参考文献：
  名称：

  共价连接的 1,8-萘酰亚胺/紫精系统中的光诱导电子转移

  摘要：

  已经合成了一系列聚亚甲基连接的 1,8-萘酰亚胺/紫精二联体。中间亚甲基的数量从 2 到 6 不等。为了比较，制备了一系列 N-烷基吡啶鎓基-1,8-萘酰亚胺“母体”化合物并对其进行光物理表征。相对于母体化合物，1,8-萘酰亚胺的电子激发单线态被发现被共价连接的紫精淬灭。根据稳态荧光光谱的 Stern-Volmer 分析，以及吡啶鎓取代的 1,8-萘酰亚胺的单线态寿命，计算出分子内猝灭的速率常数范围为 1.5 × 1010 s-1 (2中间亚甲基）至 8.3 × 107 s-1（6 个中间亚甲基）在缓冲水溶液中。为了比较，评估了 N-烷基吡啶基-1,8-萘酰亚胺的激发单重态与甲基紫精的分子间反应性。在 0.5 M 磷酸盐缓冲液 (pH 7.0) 中，发现双分子速率常数...

  DOI：

  10.1021/jp000855y

文献信息

• BISNAPHTHALIMIDOPROPYL DERIVATIVE COMPOUNDS WITH ANTI-PARASITE AND ANTI-CANCER ACTIVITY
  申请人：Cordeiro Da Silva Anabela

  公开号：US20090062329A1

  公开（公告）日：2009-03-05

  The bisnaphthalimidopropyl derivatives with anti-parasitic and anti-cancer activity. Bisnaphthalimidopropyl derivatives (A) BNIPPut, BNIPDapen, BNIPDhex, BNIPDahep, BNIPDaoct, BNIPDanon, BNTPDadec, BNIPDadod, BNPDpta, BNIPDeta were synthesized in yields ranging from 50-70 and their cytotoxicity against colon cancer cells (CaCo-2) and the parasite Leishmania infantum determined using the MTT assay and by luciferase activity present in parasite, respectively. Cytotoxicity within CaCo-2 cells was manifested with IC 50 values between 0.3 and 22 m M after 48 h of compounds incubation. Against Leishmania infantum , IC 50 values were encompassed within a narrower concentration range of 0.39-2.09 m M, for pro-mastigote form, and between 5.24 and 17.42 m M, for axenic amastigote and between 2.43 and 9.52 m M, for intracellular amastigote forms. These compounds can be an alternative to the normal therapeutic in the fields below (A), could be a solution to the toxicity and resistance related to the compounds existent in the market. Point of diversity.

  这些双萘酰亚胺丙基衍生物具有抗寄生虫和抗癌活性。双萘酰亚胺丙基衍生物（A）BNIPPut、BNIPDapen、BNIPDhex、BNIPDahep、BNIPDaoct、BNIPDanon、BNTPDadec、BNIPDadod、BNPDpta、BNIPDeta的合成产率在50-70之间，并通过MTT测定和寄生虫Leishmania infantum中的荧光素酶活性评估它们对结肠癌细胞（CaCo-2）的细胞毒性。在48小时化合物孵育后，CaCo-2细胞内的细胞毒性表现为IC50值在0.3和22 m M之间。对于Leishmania infantum，IC50值在0.39-2.09 m M的较窄浓度范围内，适用于原鞭毛体形式，以及在5.24和17.42 m M之间，适用于离体无菌性无鞭毛体和在2.43和9.52 m M之间，适用于细胞内无鞭毛体形式。这些化合物可能是以下领域中常规治疗的替代品（A），可能是解决市场上现有化合物相关毒性和耐药性的解决方案。多样性的观点。
• Photoinduced Electron Transfer in Covalently Linked 1,8-Naphthalimide/Viologen Systems
  作者：Thao P. Le、Joy E. Rogers、Lisa A. Kelly

  DOI：10.1021/jp000855y

  日期：2000.7.1

  A series of polymethylene-linked 1,8-naphthalimide/viologen diads has been synthesized. The number of intervening methylenes was varied from 2 to 6. For comparison, a series of N-alkylpyridiniumyl-1,8-naphthalimide “parent” compounds was prepared and photophysically characterized. Relative to the parent compounds, the electronically excited singlet state of the 1,8-naphthalimide was found to be quenched

  已经合成了一系列聚亚甲基连接的 1,8-萘酰亚胺/紫精二联体。中间亚甲基的数量从 2 到 6 不等。为了比较，制备了一系列 N-烷基吡啶鎓基-1,8-萘酰亚胺“母体”化合物并对其进行光物理表征。相对于母体化合物，1,8-萘酰亚胺的电子激发单线态被发现被共价连接的紫精淬灭。根据稳态荧光光谱的 Stern-Volmer 分析，以及吡啶鎓取代的 1,8-萘酰亚胺的单线态寿命，计算出分子内猝灭的速率常数范围为 1.5 × 1010 s-1 (2中间亚甲基）至 8.3 × 107 s-1（6 个中间亚甲基）在缓冲水溶液中。为了比较，评估了 N-烷基吡啶基-1,8-萘酰亚胺的激发单重态与甲基紫精的分子间反应性。在 0.5 M 磷酸盐缓冲液 (pH 7.0) 中，发现双分子速率常数...
• A Novel PAA Derivative with Enhanced Drug Efficacy in Pancreatic Cancer Cell Lines
  作者：Ali Alsuraifi、Paul Lin、Anthony Curtis、Dimitrios Lamprou、Clare Hoskins

  DOI：10.3390/ph11040091

  日期：——

  effective drug carriers in cancer therapy. Pancreatic cancer forms dense tumours which are often resistant to drug molecules. In order to overcome such multidrug resistance, new drug entities, novel delivery systems and combination therapy strategies are being explored. In this paper, we report the design and synthesis of a poly(allylamine)-based amphiphile modified with hydrophobic naphthalimido pendant groups

  纳米颗粒已被证明是癌症治疗中有效的药物载体。胰腺癌形成致密肿瘤，通常对药物分子有抵抗力。为了克服这种多药耐药性，正在探索新的药物实体、新颖的递送系统和联合治疗策略。在本文中，我们报道了用疏水性萘酰亚胺侧基修饰的聚（烯丙胺）基两亲物的设计和合成。双萘二甲酰亚胺化合物已被证明具有抗癌活性。评估了这种聚合物在 BxPC-3 细胞中封装、溶解和增强药物（5-氟尿嘧啶和双-(萘酰亚氨基丙基)-二氨基辛烷）细胞毒性的潜力。我们的研究表明，在两亲物内可分别配制高达 4.3 mg mL-1 和 2.4 mg mL-1 的不溶性药物。此外，新型聚(烯丙胺)-萘酰亚胺载体在药物处理24小时后导致细胞毒性作用放大，并且能够在浓度低至3 μg mL-1时减少50%的细胞群。
• 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.
• ——
  作者：Solange M. S. V. Wardell、Paul Kong Thoo Lin

  DOI：10.1023/a:1021796000674

  日期：——

  1,12-Bis-(N-naphthalamido)-4,9-bis-(2,4,6-trimethylbenzenesulfonyl)-4,9-diaza-dodecane 1 was obtained from 1,8-naphthalic anhydride on successive reactions with 3-aminopropanol, 4-methylbenzenesulfonyl chloride and 1,4-bis-(2,4,6-trimethylbenzenesulfonamido)butane. The molecular structure of 1 was investigated by X-ray crystallograehy, NMR, and mass spectrometry. The molecule crystallizes in the triclinic space group, . The cell parameters are a 8.1548(12), b = 15.878(3), c = 18.005(3) Angstrom, alpha = 97.685(10), beta = 93.260(15), and gamma = 101.754(11)degrees. The asymmetric unit consists of the halves of two independent molecules, with Z = 2.