N,N'-bis(mesitylsulfonyl)-4-(aminomethyl)piperidine | 165288-17-5

• 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: N,N'-bis(mesitylsulfonyl)-4-(aminomethyl)piperidine
• 英文别名: N,N'-bis(2,4,6-trimethylbenzenesulfonyl)-4-(aminomethyl)piperidine；2,4,6-trimethyl-N-[[1-(2,4,6-trimethylphenyl)sulfonylpiperidin-4-yl]methyl]benzenesulfonamide
• CAS: 165288-17-5
• 化学式: C₂₄H₃₄N₂O₄S₂
• 分子量: 478.677
• InChiKey: ZZSNCACPWGVVQA-UHFFFAOYSA-N

物化性质

• 沸点：
  632.1±65.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(mesitylsulfonyl)-4-(aminomethyl)piperidine 在 氢溴酸 、 sodium hydride 、 溶剂黄146 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 50.75h， 生成 N,N'-bis(4-piperidinylmethyl)-1,4-diaminobutane
  参考文献：
  名称：

  The role of charge in polyamine analog recognition

  摘要：

  A series of analogues and homologues of N-1,N-12-diethylspermine (DESPM) was synthesized, and their biological properties were evaluated. These tetraamines include a simple linear analogue of DESPM, N-1,N-12-bis(2,2,2-trifluoroethyl)spermine (FDESPM), the cyclic analogues of DESPM, N,N'-bis(4-piperidinylmethyl)-1,4-diaminobutane [PIP(4,4,4)] and N,N'-bis[2-(4-piperidinyl)ethyl]-1,4-diaminobutane [PIP(5,4,5)], and their aromatic counterparts, N,N'-bis(4-pyridylmethyl)-1,4-diaminobutane [PYR(4,4,4)] and N,N'-bis[2-(4-pyridyl)ethyl]-1,4-diaminobutane [PYR(5,4,5)]. The analogues FDESPM, PIP(4,4,4), and PYR(4,4,4) have distances between their nitrogen atoms almost identical to those of DESPM. The longer analogues PIP(5,4,5) and PYR(5,4,5) are very similar in the spacing of their amino groups. However, the pK(a) of the nitrogens in the groups differ; thus, the extent of protonation and the charge characteristics among the members of the groups differ. A comparison of the biological properties of these compounds clearly demonstrates that the tetraamines must be charged to be ''recognized'' by the cell. Analogues with low nitrogen pK(a)'s such that the nitrogens are poorly protonated at physiological pH do not compete well with spermidine for uptake and, as expected, have high 96 h IC50 values and have little effect on S-adenosylmethionine decarboxylase, ornithine decarboxylase, and spermidine/spermine N-1-acetyltransferase activities and on intracellular polyamine pools.

  DOI：

  10.1021/jm00013a003
• 作为产物：
  描述：

  2,4,6-三甲基苯磺酰氯 、 4-氨甲基哌啶 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到N,N'-bis(mesitylsulfonyl)-4-(aminomethyl)piperidine
  参考文献：
  名称：

  Analogs of biologically active, naturally occurring polyamines, pharmaceutical compositions and methods of treatment

  摘要：

  聚胺具有以下结构式：或其与药学上可接受的酸盐，其中：R1-R6可能相同也可能不同，是烷基、芳基、芳基烷基、环烷基，可以选择性地由至少一个醚氧原子中断的烷基链，或氢；N1、N2、N3和N4是在生理pH下能够质子化的氮原子；a和b可能相同也可能不同，是从1到4的整数；A、B和C可能相同也可能不同，是有效维持氮原子之间距离的桥接基团，使聚胺：(i)在向人类或非人类动物施用后能够被目标细胞吸收；(ii)在被目标细胞吸收后，通过正电荷氮原子之间的静电相互作用与目标细胞内的天然聚胺基本相同的生物对应阴离子竞争结合；聚胺，在细胞中与生物对应阴离子结合后，在生物学上与细胞内聚胺以不同方式发挥作用，这种聚胺在自然界中不存在；以及包含聚胺的药物组合物和治疗需要抗肿瘤治疗的患者的方法。

  公开号：

  US06342534B1

文献信息

• US5843959A
  申请人：——

  公开号：US5843959A

  公开（公告）日：1998-12-01
• US5886051A
  申请人：——

  公开号：US5886051A

  公开（公告）日：1999-03-23
• US6342534B1
  申请人：——

  公开号：US6342534B1

  公开（公告）日：2002-01-29
• US7094808B2
  申请人：——

  公开号：US7094808B2

  公开（公告）日：2006-08-22
• The role of charge in polyamine analog recognition
  作者：Raymond J. Bergeron、James S. McManis、William R. Weimar、Kathy Schreier、Fenglan Gao、Qianhong Wu、Jackqueline Ortiz-Ocasio、Gabriel R. Luchetta、Carl Porter、J. R. Timothy Vinson

  DOI：10.1021/jm00013a003

  日期：1995.6

  A series of analogues and homologues of N-1,N-12-diethylspermine (DESPM) was synthesized, and their biological properties were evaluated. These tetraamines include a simple linear analogue of DESPM, N-1,N-12-bis(2,2,2-trifluoroethyl)spermine (FDESPM), the cyclic analogues of DESPM, N,N'-bis(4-piperidinylmethyl)-1,4-diaminobutane [PIP(4,4,4)] and N,N'-bis[2-(4-piperidinyl)ethyl]-1,4-diaminobutane [PIP(5,4,5)], and their aromatic counterparts, N,N'-bis(4-pyridylmethyl)-1,4-diaminobutane [PYR(4,4,4)] and N,N'-bis[2-(4-pyridyl)ethyl]-1,4-diaminobutane [PYR(5,4,5)]. The analogues FDESPM, PIP(4,4,4), and PYR(4,4,4) have distances between their nitrogen atoms almost identical to those of DESPM. The longer analogues PIP(5,4,5) and PYR(5,4,5) are very similar in the spacing of their amino groups. However, the pK(a) of the nitrogens in the groups differ; thus, the extent of protonation and the charge characteristics among the members of the groups differ. A comparison of the biological properties of these compounds clearly demonstrates that the tetraamines must be charged to be ''recognized'' by the cell. Analogues with low nitrogen pK(a)'s such that the nitrogens are poorly protonated at physiological pH do not compete well with spermidine for uptake and, as expected, have high 96 h IC50 values and have little effect on S-adenosylmethionine decarboxylase, ornithine decarboxylase, and spermidine/spermine N-1-acetyltransferase activities and on intracellular polyamine pools.