6-(Mesitylenesulfonyl)-1,6,12-Triazadodecane | 189341-07-9

• 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: 6-(Mesitylenesulfonyl)-1,6,12-Triazadodecane
• 英文别名: N-(4-aminobutyl)-N-(5-aminopentyl)-2,4,6-trimethylbenzenesulfonamide
• CAS: 189341-07-9
• 化学式: C₁₈H₃₃N₃O₂S
• 分子量: 355.545
• InChiKey: VGMGJSNFWJITSW-UHFFFAOYSA-N

物化性质

• 沸点：
  514.6±60.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  97.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(Mesitylenesulfonyl)-1,6,12-Triazadodecane 在 sodium hydroxide 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 生成 4,9,15-tris(mesitylenesulfonyl)-4,9,15-triazaoctadecane
  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：

  5-溴戊腈 在 Raney nickel W-2 ammonium hydroxide 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、379.21 kPa 条件下， 反应 20.5h， 生成 6-(Mesitylenesulfonyl)-1,6,12-Triazadodecane
  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

文献信息

• Biologically active spermidine analogues, pharmaceutical compositions and methods of treatment
  申请人：University of Florida

  公开号：US06235794B1

  公开（公告）日：2001-05-22

  Polyamines having the formula: or a salt thereof with a pharmaceutically acceptable acid wherein: R1-R5 may be the same or different and are alkyl, aryl, aryl alkyl, cycloalkyl or hydrogen; at least one of R1 and R2 and at least one of R4 and R5 are not hydrogen, and any of the alkyl chains may optionally be interrupted by at least one etheric oxygen atom, excluding N1,N3-diethylspermidine and N1,N3-dipropylspermidine; and A and B are bridging groups which effectively maintain the distance between the nitrogen atoms such that the polyamine: (i) is capable of uptake by a target cell upon administration of the polyamine to a human or non-human animal; and (ii) upon uptake by the target cell, competitively binds via an electrostatic interaction between the positively charged nitrogen atoms to substantially the same biological counter-anions as the intracellular natural polyamines in the target cell.

  聚胺具有以下结构式：或其与药用可接受酸的盐，其中：R1-R5可以相同也可以不同，是烷基、芳基、芳基烷基、环烷基或氢；R1和R2中至少有一个，R4和R5中至少有一个不是氢，烷基链中的任何一个也可以选择性地被至少一个醚氧原子中断，但不包括N1，N3-二乙基亚精胺和N1，N3-二丙基亚精胺；A和B是桥连基，有效地保持氮原子之间的距离，使得聚胺：(i)能够在将聚胺给人类或非人类动物时被目标细胞摄取；(ii)被目标细胞摄取后，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地与生物学对应的阴离子竞争结合。
• US6235794B1
  申请人：——

  公开号：US6235794B1

  公开（公告）日：2001-05-22