trimesitylenesulfonyl norspermidine | 189339-59-1

• 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: trimesitylenesulfonyl norspermidine
• 英文别名: 2,4,6-trimethyl-N-[3-[(2,4,6-trimethylphenyl)sulfonyl-[3-[(2,4,6-trimethylphenyl)sulfonylamino]propyl]amino]propyl]benzenesulfonamide
• CAS: 189339-59-1
• 化学式: C₃₃H₄₇N₃O₆S₃
• 分子量: 677.951
• InChiKey: FDQNUSQMTOUGKP-UHFFFAOYSA-N

物化性质

• 沸点：
  809.4±75.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  45.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  129.72
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  trimesitylenesulfonyl norspermidine 在 氢溴酸 、 sodium hydride 、 苯酚 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 36.5h， 生成 diethylnorspermidine
  参考文献：
  名称：

  A Comparison of Structure−Activity Relationships between Spermidine and Spermine Analogue Antineoplastics

  摘要：

  A systematic investigation of the impact of spermidine analogues both in vitro and in vivo is described. The study characterizes the effects of these analogues on L1210 cell growth, polyamine pools, ornithine decarboxylase, S-adenosyl-L-methionine decarboxylase, spermidine/spermine N-1-acetyltransferase, the maintenance of cellular charge, i.e., cationic equivalence associated with the polyamines and their analogues, and compares their ability to compete with spermidine for transport. The findings clearly demonstrate that the activity of-the linear polyamine analogues is highly dependent on the length of the triamines and the size of the N-alpha,N-omega-substituents. It appears that there is an optimum chain length for various activities and that the larger the N-alpha,N-omega-alkyls, the less active the compound. Metabolic transformation including N-dealkylation of these compounds is also evaluated. While there is no monotonic relationship between chain length and the ability of the analogue to be metabolized, the dipropyl triamines are clearly more actively catabolized than the corresponding methyl and ethyl systems. A comparison of the triamines with the corresponding tetraamines is made throughout the text regarding both in vitro activity against L1210 cells and in vivo toxicity measurements, suggesting that several triamine analogues may offer therapeutic advantages over the corresponding tetraamines.

  DOI：

  10.1021/jm960849j
• 作为产物：
  描述：

  3,3'-二氨基二丙基胺 、 2,4,6-三甲基苯磺酰氯 在 吡啶 作用下， 反应 4.0h， 以67%的产率得到trimesitylenesulfonyl norspermidine
  参考文献：
  名称：

  The synthesis and the in vitro cytotoxicity studies of bisnaphthalimidopropyl polyamine derivatives against colon cancer cells and parasite Leishmania infantum

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2006.09.031

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。