1,7-bis[3-(phenylseleno)propyl]-1,4,7,10-tetraazacyclododecane | 1085526-30-2

• 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: 1,7-bis[3-(phenylseleno)propyl]-1,4,7,10-tetraazacyclododecane
• 英文别名: 1,7-Bis(3-phenylselanylpropyl)-1,4,7,10-tetrazacyclododecane
• CAS: 1085526-30-2
• 化学式: C₂₆H₄₀N₄Se₂
• 分子量: 566.55
• InChiKey: KBMFRPFEPMGZFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  30.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3-bromopropyl)(phenyl)selane 、 轮环藤宁 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以29.8%的产率得到1,7-bis[3-(phenylseleno)propyl]-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  The Design of Multifunctional Antioxidants Against the Damaging Ingredients of Oxidative Stress

  摘要：

  Oxidative stress is a biochemical condition associated with a sharp increase in intracellular concentrations of a range of oxidative stressors, including reactive oxygen species, reactive nitrogen species and labile metal ions. It is associated with a wide range of human disorders, such as inflammatory diseases, neurodegenerative diseases, glaucoma, and cancer. Equally importantly, oxidative stress is pronounced in older people, which makes it an important matter in an ageing Society. Not surprisingly, antioxidants have become a major focus of modern drug development. While natural antioxidants, such as phenolic aromatic compounds, vitamin C, vitamin E and curcumin have shown promising results, the development of effective synthetic antioxidants is often problematic. We have recently proposed the rational design of multifunctional antioxidants which target oxidative stressors in a more comprehensive manner. Such compounds may, for instance, combine catalytic sites with metal binding sites. Here we present the synthesis of representative molecules with combined catalytic and metal binding properties. The apparent 'antioxidant' activities have been studied in vitro and, for the most promising compound, have been confirmed in cultured skin cells exposed to UVA radiation.

  DOI：

  10.1080/10426500801898200

文献信息

• Exploring synthetic avenues for the effective synthesis of selenium- and tellurium-containing multifunctional redox agents
  作者：Susanne Mecklenburg、Saad Shaaban、Lalla A. Ba、Torsten Burkholz、Thomas Schneider、Britta Diesel、Alexandra K. Kiemer、Anne Röseler、Katja Becker、Jörg Reichrath、Alexandra Stark、Wolfgang Tilgen、Muhammad Abbas、Ludger A. Wessjohann、Florenz Sasse、Claus Jacob

  DOI：10.1039/b907831b

  日期：——

  Various human illnesses, including several types of cancer and infectious diseases, are related to changes in the cellular redox homeostasis. During the last decade, several approaches have been explored which employ such disturbed redox balances for the benefit of therapy. Compounds able to modulate the intracellular redox state of cells have been developed, which effectively, yet also selectively, appear to kill cancer cells and a range of pathogenic microorganisms. Among the various agents employed, certain redox catalysts have shown considerable promise since they are non-toxic on their own yet develop an effective, often selective cytotoxicity in the presence of the ‘correct’ intracellular redox partners. Aminoalkylation, amide coupling and multicomponent reactions are suitable synthetic methods to generate a vast number of such multifunctional catalysts, which are chemically diverse and, depending on their structure, exhibit various interesting biological activities.

  人类的各种疾病，包括几种癌症和传染病，都与细胞氧化还原平衡的变化有关。过去十年间，人们探索了几种方法，利用这种紊乱的氧化还原平衡来进行治疗。目前已开发出能够调节细胞内氧化还原状态的化合物，这些化合物能够有效但也有选择性地杀死癌细胞和一系列病原微生物。在所使用的各种药剂中，某些氧化还原催化剂显示出相当大的前景，因为它们本身无毒，但在 "正确的 "细胞内氧化还原伙伴存在的情况下，会产生有效的、通常是选择性的细胞毒性。氨基烷基化、酰胺偶联和多组分反应是生成大量此类多功能催化剂的合适合成方法。
• The Design of Multifunctional Antioxidants Against the Damaging Ingredients of Oxidative Stress
  作者：Susanne Mecklenburg、Catriona A. Collins、Mandy Döring、Torsten Burkholz、Muhammad Abbas、Fiona H. Fry、Charareh Pourzand、Claus Jacob

  DOI：10.1080/10426500801898200

  日期：2008.4.1

  Oxidative stress is a biochemical condition associated with a sharp increase in intracellular concentrations of a range of oxidative stressors, including reactive oxygen species, reactive nitrogen species and labile metal ions. It is associated with a wide range of human disorders, such as inflammatory diseases, neurodegenerative diseases, glaucoma, and cancer. Equally importantly, oxidative stress is pronounced in older people, which makes it an important matter in an ageing Society. Not surprisingly, antioxidants have become a major focus of modern drug development. While natural antioxidants, such as phenolic aromatic compounds, vitamin C, vitamin E and curcumin have shown promising results, the development of effective synthetic antioxidants is often problematic. We have recently proposed the rational design of multifunctional antioxidants which target oxidative stressors in a more comprehensive manner. Such compounds may, for instance, combine catalytic sites with metal binding sites. Here we present the synthesis of representative molecules with combined catalytic and metal binding properties. The apparent 'antioxidant' activities have been studied in vitro and, for the most promising compound, have been confirmed in cultured skin cells exposed to UVA radiation.