6,7-methylenedioxyquinoline-4-carboxylic acid N-[2-(N-benzyl-N-methylamino)ethyl]-N-(2-iodo-4,5-dimethoxyphenyl)amide | 884850-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6,7-methylenedioxyquinoline-4-carboxylic acid N-[2-(N-benzyl-N-methylamino)ethyl]-N-(2-iodo-4,5-dimethoxyphenyl)amide
• CAS: 884850-53-7
• 化学式: C₂₉H₂₈IN₃O₅
• 分子量: 625.463
• InChiKey: SJMYFDZTXYLPMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  73.36
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6,7-methylenedioxyquinoline-4-carboxylic acid N-[2-(N-benzyl-N-methylamino)ethyl]-N-(2-iodo-4,5-dimethoxyphenyl)amide 在 四(三苯基膦)钯 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以21%的产率得到13-[2-(Benzyl-methyl-amino)-ethyl]-2,3-dimethoxy-13H-8,10-dioxa-6,13-diaza-cyclopenta[b]chrysen-12-one
  参考文献：
  名称：

  6-Substituted 6H-dibenzo[c,h][2,6]naphthyridin-5-ones: Reversed lactam analogues of ARC-111 with potent topoisomerase I-targeting activity and cytotoxicity

  摘要：

  6-substituted 8,9-dimethoxy-2,3-methylenedioxy-6H-dibenzo[c,h][2,6]naphtyridin-5-ones were synthesized and evaluated for topoisomerase I-targeting activity and cytotoxicity. Several of these reversed lactam analogues of ARC-111 exhibited exceptional cytotoxicity with IC50 values ranging from 0.5 to 3.0 nM. In contrast to topotecan, no resistance was observed with several of these reversed lactam analogues in tumor cell lines that overexpressed the efflux transporters MDR1 or BCRP. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.028
• 作为产物：
  描述：

  4,5-二甲氧基-2-碘苯胺 在 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6,7-methylenedioxyquinoline-4-carboxylic acid N-[2-(N-benzyl-N-methylamino)ethyl]-N-(2-iodo-4,5-dimethoxyphenyl)amide
  参考文献：
  名称：

  6-Substituted 6H-dibenzo[c,h][2,6]naphthyridin-5-ones: Reversed lactam analogues of ARC-111 with potent topoisomerase I-targeting activity and cytotoxicity

  摘要：

  6-substituted 8,9-dimethoxy-2,3-methylenedioxy-6H-dibenzo[c,h][2,6]naphtyridin-5-ones were synthesized and evaluated for topoisomerase I-targeting activity and cytotoxicity. Several of these reversed lactam analogues of ARC-111 exhibited exceptional cytotoxicity with IC50 values ranging from 0.5 to 3.0 nM. In contrast to topotecan, no resistance was observed with several of these reversed lactam analogues in tumor cell lines that overexpressed the efflux transporters MDR1 or BCRP. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.028