5,10,15-tris(mesitylenesulfonyl)-5,10,15-triaza-1-heptadecylamine | 618436-57-0

• 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: 5,10,15-tris(mesitylenesulfonyl)-5,10,15-triaza-1-heptadecylamine
• 英文别名: N-[4-[4-[4-aminobutyl-(2,4,6-trimethylphenyl)sulfonylamino]butyl-(2,4,6-trimethylphenyl)sulfonylamino]butyl]-N-ethyl-2,4,6-trimethylbenzenesulfonamide
• CAS: 618436-57-0
• 化学式: C₄₁H₆₄N₄O₆S₃
• 分子量: 805.18
• InChiKey: SDYYKIMIENGFDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  54
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  163
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,10,15-tris(mesitylenesulfonyl)-5,10,15-triaza-1-heptadecylamine 在 sodium hydroxide 、 sodium hydride 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 3,8,13,18-tetrakis(mesitylenesulfonyl)-3,8,13,18-tetraazaheneicosanecyanide
  参考文献：
  名称：

  Cyclopropane-Containing Polyamine Analogues Are Efficient Growth Inhibitors of a Human Prostate Tumor Xenograft in Nude Mice

  摘要：

  Polyamine analogues 7, 10, 18, 27, and 32 containing cyclopropane rings were obtained by chemical synthesis. Their antineoplastic activities were assessed against the cultured human prostate tumor cell lines DU-145, DuPro, and PC-3. Decamines 32 and 27 exhibited variable levels of cytotoxicity against all three cell lines, while 7, 10, and 18 were efficacious against DU-145 and DuPro. Maximum tolerated doses (MTD) for all five compounds in a NCr-nu mouse model were determined at dosing schedules of q1d x 5 (ip) in two cycles with a break of 10 days between cycles. Their antitumor efficacies were then tested against DU-145 tumor xenografts in mice treated with all five agents at their respective MTDs. In addition, the efficacies of 7 and 10 against the same tumor xenograft were assessed at doses below their respective MTDs. In all experiments, administration began two weeks after tumor implantation. All compounds efficiently inhibited tumor growth for up to 50 days postimplantation, with negligible animal body weight loss. Tetramine 10 and hexamine 18 were the most efficient among the five analogues in arresting tumor growth. Tetramine 10 containing two cyclopropane rings had the lowest systemic toxicity as reflected in animal body weight loss. It was further assessed at a weekly administration regimen of (q1w x 4) in two cycles with a four-week break between the cycles. At this dosing schedule, 10 again efficiently arrested tumor growth with negligible effect on animal body weight. Tetramine 10 also arrested the growth of large tumors (ca. 2000 mm(3)) treated 66 days postimplantation. Studies on the metabolism of 10 showed that it accumulates in tumor within 6 h after the end of administration and reached a maximum level 72 h after cessation of dosing. Intracellular concentrations of 10 in liver and kidney were much smaller when compared to those in the tumor when measured 72 h after cessation of dosing. In liver and kidney, the deethyl metabolites of 10 accumulated over a 96 h period after cessation of dosing.

  DOI：

  10.1021/jm030175u
• 作为产物：
  描述：

  N-ethylmesitylenesulfonamide 在 sodium hydride 、 一水合肼 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5,10,15-tris(mesitylenesulfonyl)-5,10,15-triaza-1-heptadecylamine
  参考文献：
  名称：

  SYNTHESIS AND GROWTH REGULATORY ACTIVITY OF A PROTOTYPE MEMBER OF A NEW FAMILY OF AMlNOTHIOL RADIOPROTECTORS

  摘要：

  报道了PrC-210氨硫醇，3-(甲氨基)-2-((甲氨基)甲基)丙烷-1-硫醇及其多胺和硫化多胺前体的合成、生长抑制和放射防护活性。所有分子均显著抑制培养的正常人类成纤维细胞的生长。具有ROS清除硫基团和带正电的烷基胺骨架的组合提供了最具放射防护性的氨硫醇分子。

  公开号：

  US20140107216A1

文献信息

• Synthesis and growth regulatory activity of a prototype member of a new family of aminothiol radioprotectors
  作者：Richard R. Copp、Daniel D. Peebles、William E. Fahl

  DOI：10.1016/j.bmcl.2011.10.011

  日期：2011.10

  The synthesis, growth inhibition and radioprotective activity of the PrC-210 aminothiol, 3-(methylamino)-2-((methylamino) methyl)propane-1-thiol, and its polyamine and thiolated polyamine progenitors are reported. All of the molecules significantly inhibited growth of cultured normal human fibroblasts. The combination of an ROS-scavenging thiol group and a positively charged alkyl-amine backbone provided the most radioprotective aminothiol molecule. (C) 2011 Elsevier Ltd. All rights reserved.
• US7314959B2
  申请人：——

  公开号：US7314959B2

  公开（公告）日：2008-01-01
• US7414154B2
  申请人：——

  公开号：US7414154B2

  公开（公告）日：2008-08-19