2-(4-methoxy-2-nitrophenyl)-6,7-dimethoxy-1-naphthaldehyde | 227951-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-methoxy-2-nitrophenyl)-6,7-dimethoxy-1-naphthaldehyde
• 英文别名: 2-(4-Methoxy-6-nitrophenyl)-6,7-dimethoxy-1-naphthaldehyde；6,7-dimethoxy-2-(4-methoxy-2-nitrophenyl)naphthalene-1-carbaldehyde
• CAS: 227951-14-6
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: CLKDNYCZBFDPIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-methoxy-2-nitrophenyl)-6,7-dimethoxy-1-naphthaldehyde 在 锌 溶剂黄146 、 氯仿 、 碳酸氢钠 、 Brine 、 silica 、 hexanes 、 乙酸乙酯 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以ethyl acetate as eluent to give the title compound (20 mg, 77%)的产率得到2,3,8-Trimethoxy-benzo[i]phenanthridine
  参考文献：
  名称：

  Heterocyclic cytotoxic agents

  摘要：

  本发明提供了公式I的化合物：其中R取代基和原子X和Y的定义如规范中所述。本发明还提供了制药组合物和抑制癌细胞生长的方法。

  公开号：

  US06486167B1
• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢-1H-2-萘酮 在 四(三苯基膦)钯 三溴化磷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 copper(I) bromide 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 为溶剂， 反应 29.0h， 生成 2-(4-methoxy-2-nitrophenyl)-6,7-dimethoxy-1-naphthaldehyde
  参考文献：
  名称：

  2,3-Dimethoxybenzo[i]phenanthridines: topoisomerase I-targeting anticancer agents

  摘要：

  Appropriately substituted benzo[i]phenanthridines structurally related to nitidine, a benzo[c]phenanthridine alkaloid with antitumor activity, are active as topoisomerase 1-targeting agents. Studies on benzo[i]phenanthridines have indicated analogues that possess a 2,3-methylenedioxy moiety and at least one and preferably two methoxyl groups at the 8- and 9-positions, such as 8,9-dimethoxy-2,3-methylenedioxybenzo[i]phenanthridine, 2, are active as topoisomerase 1-targeting agents. Tetramethoxylated benzo[i]phenanthridines, wherein the 2,3-methylenedioxy moiety is replaced with methoxyl groups at the 2- and 3-position, are inactive as a topoisomerase 1-targeting agent. These results initially suggested that the 2,3-methylenedioxy moiety was critical to the retention of potent activity. Further studies revealed that 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine, 7a, is more potent than 2 as a topoisomerase 1-targeting agent. The observation that 2,3-dimethoxylated benzo[i]phenanthridines can actually exhibit enhanced activity prompted the present study in which several 8-substituted 2,3-dimethoxybenzo[i]phenanthridines were prepared and their pharmacological activities evaluated. The influence of NH2, CN, CH2OH, OBn, OCH3, OH, and NHCOCH3 substituents at the 8-position on the relative activity of these 2,3 -dimethoxybenzo[i]phenanthridines was examined. Relative to these derivatives, 7a was the most potent topoisomerase I-targeting agent, possessing similar cytotoxicity to that of nitidine in the human lymphoblast tumor cell line, RPMI8402. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00530-8

文献信息

• Heterocyclic cytotoxic agents
  申请人：Rutgers, The State University of New Jersey

  公开号：US06486167B1

  公开（公告）日：2002-11-26

  The present invention provides compounds of formula I: wherein the R substituents and atoms X and Y are as defined in specification. The present invention also provides pharmaceutical compositions and methods of inhibiting cancer cell growth.

  本发明提供了公式I的化合物：其中R取代基和原子X和Y的定义如规范中所述。本发明还提供了制药组合物和抑制癌细胞生长的方法。
• HETEROCYCLIC CYTOTOXIC AGENTS
  申请人：RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY

  公开号：EP1042294B1

  公开（公告）日：2004-08-11
• US6486167B1
  申请人：——

  公开号：US6486167B1

  公开（公告）日：2002-11-26
• [EN] HETEROCYCLIC CYTOTOXIC AGENTS<br/>[FR] AGENTS CYTOTOXIQUES HETEROCYCLIQUES
  申请人：RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY

  公开号：WO1999031067A1

  公开（公告）日：1999-06-24

  (EN) The invention provides compounds of formula (I) wherein R1-R8 and X and Y 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).(FR) L'invention concerne des composés de formule (I): dans laquelle R1-R8 et X et Y ont l'une des significations spécifiées dans le descriptif, ainsi que leurs sels pharmaceutiquement acceptables. L'invention concerne également des compositions pharmaceutiques renfermant un composé de formule (I), des procédés de préparation des composés de formule (I), des produits intermédiaires utiles pour la préparation de composés de formule (I), ainsi que des procédés thérapeutiques de traitement du cancer à l'aide des composés de formule (I).
• 2,3-Dimethoxybenzo[i]phenanthridines: topoisomerase I-targeting anticancer agents
  作者：Dajie Li、Baoping Zhao、Sai-Peng Sim、Tsai-Kun Li、Angela Liu、Leroy F Liu、Edmond J LaVoie

  DOI：10.1016/s0968-0896(02)00530-8

  日期：2003.2

  Appropriately substituted benzo[i]phenanthridines structurally related to nitidine, a benzo[c]phenanthridine alkaloid with antitumor activity, are active as topoisomerase 1-targeting agents. Studies on benzo[i]phenanthridines have indicated analogues that possess a 2,3-methylenedioxy moiety and at least one and preferably two methoxyl groups at the 8- and 9-positions, such as 8,9-dimethoxy-2,3-methylenedioxybenzo[i]phenanthridine, 2, are active as topoisomerase 1-targeting agents. Tetramethoxylated benzo[i]phenanthridines, wherein the 2,3-methylenedioxy moiety is replaced with methoxyl groups at the 2- and 3-position, are inactive as a topoisomerase 1-targeting agent. These results initially suggested that the 2,3-methylenedioxy moiety was critical to the retention of potent activity. Further studies revealed that 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine, 7a, is more potent than 2 as a topoisomerase 1-targeting agent. The observation that 2,3-dimethoxylated benzo[i]phenanthridines can actually exhibit enhanced activity prompted the present study in which several 8-substituted 2,3-dimethoxybenzo[i]phenanthridines were prepared and their pharmacological activities evaluated. The influence of NH2, CN, CH2OH, OBn, OCH3, OH, and NHCOCH3 substituents at the 8-position on the relative activity of these 2,3 -dimethoxybenzo[i]phenanthridines was examined. Relative to these derivatives, 7a was the most potent topoisomerase I-targeting agent, possessing similar cytotoxicity to that of nitidine in the human lymphoblast tumor cell line, RPMI8402. (C) 2002 Elsevier Science Ltd. All rights reserved.