6,7-methylenedioxyquinoline-4-carboxylic acid | 60597-63-9

• 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
• 英文别名: [1,3]Dioxolo[4,5-g]quinoline-8-carboxylic acid
• CAS: 60597-63-9
• 化学式: C₁₁H₇NO₄
• 分子量: 217.181
• InChiKey: CKWDMJXZENTKCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-methylenedioxyquinoline-4-carboxylic acid 在 四(三苯基膦)钯 氯化亚砜 、 sodium hydride 、 三乙胺 、 silver carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 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：

  3,4-亚甲二氧基苯胺 在 吡啶 、 potassium permanganate 、 selenium(IV) oxide 、 三氯化铁 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 生成 6,7-methylenedioxyquinoline-4-carboxylic acid
  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

文献信息

• 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
  作者：Alexander L. Ruchelman、Shejin Zhu、Nai Zhou、Angela Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1016/j.bmcl.2004.08.070

  日期：2004.11

  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.
• Potent In vitro methicillin-resistant Staphylococcus aureus activity of 2-(1H-indol-3-yl)quinoline derivatives
  作者：Michael Z. Hoemann、G. Kumaravel、Roger L. Xie、Richard F. Rossi、Sylvia Meyer、Alban Sidhu、Gregory D. Cuny、James R. Hauske

  DOI：10.1016/s0960-894x(00)00542-4

  日期：2000.12

  A novel structural class of antibacterials, 2-(1H-indol-3-yl)quinolines, effective against methicillin-resistant Staphylococcus aureus (MRSA), was discovered from a combinatorial library. A structure-activity relationship (SAR) study was conducted to determine the pharmacophore and increase the potency of these compounds. Compounds were prepared that had minimum inhibitory concentrations (MICs) < 1.0 g/mL against MRSA and retained activity against two strains of glycopeptide intermediate-resistant S. aureus (GISA). (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.
• 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
  作者：Shejin Zhu、Alexander L. Ruchelman、Nai Zhou、Angela Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1016/j.bmc.2005.12.028

  日期：2006.5

  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.