4-Ethylbenzo[g]quinoline-5,10-dione | 143858-53-1

• 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: 4-Ethylbenzo[g]quinoline-5,10-dione
• 英文别名: Homocleistopholine
• CAS: 143858-53-1
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: VALOMJWQXIJEDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 4-Ethylbenzo[g]quinoline-5,10-dione 在 氯化铵 、 溶剂黄146 作用下， 生成 4'-oxohomocleistopholine 、 3-methylsampangine 、 2,3-dihydro-4'-ethyl-3α-methylspiro<7H-naphtho<1,2,3-ij><2,7>naphthyridine-2α,10'-benzoquinoline>-5',7-dione
  参考文献：
  名称：

  Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines

  摘要：

  Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of the sampangine B-ring at position 4, while the synthesis of A-ring 3-substituted sampangines and benzo[4,5]sampangine (24) were achieved from the corresponding functionalized cleistopholines. Two-dimensional NMR spectroscopy was used to rigorously characterize the A- and B-ring substituent patterns. Structure-activity relationship studies revealed the activity of the sampangines was enhanced by the presence of a substituent at position 3 or by a 4,5-benzo group.

  DOI：

  10.1021/jm00100a012
• 作为产物：
  描述：

  2-溴-1,4-萘醌 、 1,1-dimethyl-2-((E)-pent-2-en-1-ylidene)hydrazine 在 chloroformyl polystyrene resin 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以38%的产率得到4-Ethylbenzo[g]quinoline-5,10-dione
  参考文献：
  名称：

  Improvements in the Hetero Diels-Alder Reactions of 1-Dimethylamino-1-azadienes in the Presence of an Electrophilic Scavenger Resin

  摘要：

  1-二甲氨基-1-氮杂二烯和几种醌在氯甲酰聚苯乙烯树脂存在下进行反应，由于有效清除了从伯胺中释放出的二甲胺，杂狄尔斯-阿尔德产物的分离收率增加了 2.5 倍。环加合物。

  DOI：

  10.1055/s-2000-6501

文献信息

• Compounds and compositions useful as antifungal and antimycobacterial
  申请人：The University of Mississippi

  公开号：US05227383A1

  公开（公告）日：1993-07-13

  New analogs of sampangine and cleistopholine, compositions and methods of preparation thereof, method of treating fungal and mycobacterial infections. The compounds have the general formula: ##STR1## where the R.sub.1, R.sub.2, and R.sub.5 groups are defined herein.

  新的sampangine和cleistopholine的类似物，其组成物和制备方法，治疗真菌和分枝杆菌感染的方法。这些化合物具有一般公式：##STR1##其中R.sub.1、R.sub.2和R.sub.5基团在此处被定义。
• Antimycobacterial method
  申请人：The University of Mississippi

  公开号：US05530004A1

  公开（公告）日：1996-06-25

  New analogs of sampangine and cleistopholine, compositions and methods of preparation thereof, method of treating fungal and mycobacterial infections.

  新的sampangine和cleistopholine类似物，其组合物和制备方法，以及治疗真菌和分枝杆菌感染的方法。
• SAMPANGINE DERIVATIVES USEFUL AS ANTIFUNGAL AND ANTIMYCOBACTERIAL AGENTS
  申请人：THE UNIVERSITY OF MISSISSIPPI

  公开号：EP0588796B1

  公开（公告）日：2001-04-04
• NEW COMPOUNDS AND COMPOSITIONS USEFUL AS ANTIFUNGAL AND ANTIMYCOBACTERIAL AGENTS
  申请人：THE UNIVERSITY OF MISSISSIPPI, Research Institute of Pharmaceutical

  公开号：EP0588796A1

  公开（公告）日：1994-03-30
• US5227383A
  申请人：——

  公开号：US5227383A

  公开（公告）日：1993-07-13