6,7-methylenedioxyquinoline-4-carboxylic acid N-(2-iodo-4,5-dimethoxyphenyl)amide | 550372-56-0

• 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-iodo-4,5-dimethoxyphenyl)amide
• 英文别名: N-(2-iodo-4,5-dimethoxyphenyl)-[1,3]dioxolo[4,5-g]quinoline-8-carboxamide
• CAS: 550372-56-0
• 化学式: C₁₉H₁₅IN₂O₅
• 分子量: 478.243
• InChiKey: QLCJVZOTKDNBSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-methylenedioxyquinoline-4-carboxylic acid N-(2-iodo-4,5-dimethoxyphenyl)amide 在 四(三苯基膦)钯 sodium hydride 、 silver carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 13-(2-Dibenzylamino-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-methyl-6,7-methylenedioxyquinoline 在 吡啶 、 potassium permanganate 、 selenium(IV) oxide 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 6,7-methylenedioxyquinoline-4-carboxylic acid N-(2-iodo-4,5-dimethoxyphenyl)amide
  参考文献：
  名称：

  Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity

  摘要：

  The exceptional TOP1-targeting activity and antitumor activity of ARC-111, 1, prompted studies on similarly substituted benzo[i]phenanthridine-12-carboxylic ester and amide derivatives. These studies were extended to include 6-substituted 8,9-dimethoxy-2,3-methylenedioxy-dibenzo [c,h] [2,6]naphthyridin-5-ones, which represent reversed lactam analogues of 1. Several of these analogues retained the potent TOP1-targeting activity and cytotoxicity observed for ARG-111. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.070

文献信息

• SOLUBILIZED TOPOISOMERASE POISON AGENTS
  申请人：LaVoie Edmond J.

  公开号：US20100240664A1

  公开（公告）日：2010-09-23

  The invention provides compounds of formula I: wherein A, B, W, Y, Z, and R 1 have any of the meanings defined in the specification and their pharmaceutically acceptable salts. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I, and therapeutic methods for treating cancer using compounds of formula I.