5-methoxy-6-nitro-7H-dibenzo[de,h]quinolin-7-one | 1255674-82-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 异卟啉
• 英文名称: 5-methoxy-6-nitro-7H-dibenzo[de,h]quinolin-7-one
• 英文别名: 11-Methoxy-10-nitro-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one
• CAS: 1255674-82-8
• 化学式: C₁₇H₁₀N₂O₄
• 分子量: 306.277
• InChiKey: RQKZSECOVAPECY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methoxy-6-nitro-7H-dibenzo[de,h]quinolin-7-one 在 sodium sulfide 作用下， 生成 lakshminine
  参考文献：
  名称：

  取代蒽-9,10-二酮的环化产生有前途的选择性抗增殖化合物

  摘要：

  蒽醌衍生物是众所周知的抗增殖化合物，目前一些被用于癌症化学疗法中。还已经研究了一些环状的蒽醌​​类似物的抗增殖活性，但是在这方面，几乎没人知道1-氮杂苯并蒽酮（7 H-二苯并[ de，h ]喹啉-7-酮）。测试了一系列的1-氮杂苯并蒽醌衍生物，它们的2,3-二氢类似物和同等取代的9,10-蒽二酮对正常的人类成纤维细胞和四种人类癌细胞系。多数杂环化合物被证明对IC 50具有弱至中度的抗增殖作用该值向下延伸至0.86μM，并且在癌症和正常细胞之间表现出高达30倍的选择性。1-氮杂苯并蒽酮和1-氮杂-2,3-二氢苯并蒽酮均比蒽醌类更有效，几乎毫无例外，2,3-二氢化合物比完全芳族的1-氮杂苯并蒽酮更有效。

  DOI：

  10.1016/j.ejmech.2013.01.049
• 作为产物：
  描述：

  5-methoxy-6-nitro-1-azabenzanthrone 在 palladium on carbon 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以87%的产率得到5-methoxy-6-nitro-7H-dibenzo[de,h]quinolin-7-one
  参考文献：
  名称：

  Synthesis of Lakshminine and Antiproliferative Testing of Related Oxoisoaporphines

  摘要：

  Lakshminine (6-amino-l-aza-5-methoxy-7H-dibenzo[de,h]quinolin-7-one, 1) is a recent addition to the small family of oxoisoaporphine alkaloids and a member of an even smaller set bearing an amino group at C-6. This rare natural product has now been synthesized in order to have sufficient amounts for biological testing. Lakshminine, its 4-amino isomer (2), their 6- and 4-nitro precursors (8 and 10, respectively), the intermediate 5-methoxy-7H-dibenzo[de,h]quinolin-7-one (6), and the unsubstituted skeleton (11) were tested against normal human fibroblasts and three human solid tumor cell lines. Only compound 10 showed marginal antiproliferative activity.

  DOI：

  10.1021/np100370g

文献信息

• Synthesis and antiplasmodial activity of some 1-azabenzanthrone derivatives
  作者：Vicente Castro-Castillo、Cristian Suárez-Rozas、Adriana Pabón、Edwin G. Pérez、Bruce K. Cassels、Silvia Blair

  DOI：10.1016/j.bmcl.2012.10.092

  日期：2013.1

  Some synthetic 1-azabenzanthrones (7H-dibenzo[de,h]quinolin-7-ones) are weakly to moderately cytotoxic, suggesting that they might also show antiparasitic activity. We have now tested a small collection of these compounds in vitro against a chloroquine-resistant Plasmodium falciparum strain, comparing their cytotoxicity against normal human fibroblasts. Our results indicate that 5-methoxy-1-azabenzanthrone and its 2,3-dihydro analogue have low micromolar antiplasmodial activities and showed more than 10-fold selectivity against the parasite, indicating that the dihydro compound, in particular, might serve as a lead compound for further development. (C) 2012 Elsevier Ltd. All rights reserved.