6-(3-((2,6-di-Boc-aminohex-1-yl)amino)propyl)-6H-indeno[1,2-c]isoquinoline-5,11-dione | 1259521-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-(3-((2,6-di-Boc-aminohex-1-yl)amino)propyl)-6H-indeno[1,2-c]isoquinoline-5,11-dione
• CAS: 1259521-31-7
• 化学式: C₃₅H₄₆N₄O₆
• 分子量: 618.773
• InChiKey: HOACVXJDSUKWPY-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  6-(3-((2,6-di-Boc-aminohex-1-yl)amino)propyl)-6H-indeno[1,2-c]isoquinoline-5,11-dione 在 盐酸 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 18.0h， 以55%的产率得到6-(3-((2,6-diaminohex-1-yl)amino)propyl)-6H-indeno[1,2-c]-isoquinoline-5,11-dione trihydrochloride
  参考文献：
  名称：

  Indeno[1,2-c]isoquinolin-5,11-diones conjugated to amino acids: Synthesis, cytotoxicity, DNA interaction, and topoisomerase II inhibition properties

  摘要：

  Three series of indeno[1,2-c]isoquinolin-5,11-dione-amino acid conjugates were designed and synthesized. Amino acids were connected to the tetracycle through linkers with lengths of n = 2 and 3 atoms using ester (series I), amide (series II), and secondary amine (series III) functions. DNA binding was evaluated by thermal denaturation and fluorescence measurements. Lysine and arginine substituted derivatives with n = 3 provided the highest DNA binding. Arginine derivative 32 (n = 2, series II) and glycine derivative 34 (n = 2, series III) displayed high topoisomerase II inhibition. Incrementing the length of the N-6 side chain from two to three methylene units provided a significant increase in DNA affinity but a substantial loss in topoisomerase II inhibition. The most cytotoxic compounds toward HL60 leukemia cells were 19, 33, and 34 displaying micromolar IC50 values. When tested with the topoisomerase II-mutated HL60/MX2 cell line, little variation of IC50 values was found, suggesting that topoisomerase II might not be the main target of these compounds and that additional targets could be involved. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.025
• 作为产物：
  描述：

  tert-butyl N-[6-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxohexan-2-yl]carbamate 、 5,6-dihydro-5,11-dioxo-5-(3-aminopropyl)-11H-indeno(1,2-c)isoquinoline hydrochloride 在 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 以0.33 g的产率得到6-(3-((2,6-di-Boc-aminohex-1-yl)amino)propyl)-6H-indeno[1,2-c]isoquinoline-5,11-dione
  参考文献：
  名称：

  Indeno[1,2-c]isoquinolin-5,11-diones conjugated to amino acids: Synthesis, cytotoxicity, DNA interaction, and topoisomerase II inhibition properties

  摘要：

  Three series of indeno[1,2-c]isoquinolin-5,11-dione-amino acid conjugates were designed and synthesized. Amino acids were connected to the tetracycle through linkers with lengths of n = 2 and 3 atoms using ester (series I), amide (series II), and secondary amine (series III) functions. DNA binding was evaluated by thermal denaturation and fluorescence measurements. Lysine and arginine substituted derivatives with n = 3 provided the highest DNA binding. Arginine derivative 32 (n = 2, series II) and glycine derivative 34 (n = 2, series III) displayed high topoisomerase II inhibition. Incrementing the length of the N-6 side chain from two to three methylene units provided a significant increase in DNA affinity but a substantial loss in topoisomerase II inhibition. The most cytotoxic compounds toward HL60 leukemia cells were 19, 33, and 34 displaying micromolar IC50 values. When tested with the topoisomerase II-mutated HL60/MX2 cell line, little variation of IC50 values was found, suggesting that topoisomerase II might not be the main target of these compounds and that additional targets could be involved. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.025