1'-butyl-1',4'-dihydro-2,3'-biquinolin-4'-one | 297744-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1'-butyl-1',4'-dihydro-2,3'-biquinolin-4'-one
• 英文别名: 1-butyl-3-(2-quinolyl)-1,4-dihydro-4-quinolone；1'-butyl-1',4'-dihydro-2,3'-biquinolyl-4'-one；1'-butyl-2,3'-biquinolin-4'(1'H)-one；1-butyl-3-quinolin-2-ylquinolin-4-one
• CAS: 297744-16-2
• 化学式: C₂₂H₂₀N₂O
• 分子量: 328.414
• InChiKey: BMVAYUWZOBNOBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1'-butyl-1',4'-dihydro-2,3'-biquinolin-4'-one 在 硫酸 、 硝酸 作用下， 反应 0.5h， 以89%的产率得到1'-butyl-6,6'-dinitro-1',4'-dihydro-2,3'-biquinolin-4'-one
  参考文献：
  名称：

  The investigation in 2,3'-biquinoline series 26.* Regioselective nitration of 1'-alkyl-1',4'-dihydro-2,3'-biquinolin-4'-ones and 1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones

  摘要：

  The nitration of 1'-alkyl-1',4'-dihydro-2,3'-biquinolin-4'-ones and 1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones has been investigated. It was shown that the regioselectivity of nitration of the first depends on the acidity of the medium and the order of adding reactants. In strongly acidic medium 1'-alkyl-5,6'-dinitro-1',4'-dihydro-2,3'-biquinolin-4'-ones or mixtures of them with 1'-alkyl-5-nitro-1',4'-dihydro-2,3'-biquinolin-4'-ones are formed. In less acidic media 1'-alkyl-6'-nitro-1',4'-dihydro-2,3'-biquinolin-4'-ones and then 1'-alkyl-6,6'-dinitro-1',4'-dihydro-2,3'-biquinolin-4'-ones are formed. Nitration of 1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones leads to 1'-alkyl-6'-nitro-1',2'-dihydro-2,3'-biquinolin-2'-one and then 1'-alkyl-6,6',8'-trinitro-1',2'-dihydro-2,3'-biquinolin-2'-one.

  DOI：

  10.1007/s10593-009-0285-8
• 作为产物：
  描述：

  1-butyl-3-(2-quinolyl)quinolinium iodide 在 氢氧化钾 、 magnesium(II) perchlorate 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以50%的产率得到1'-butyl-1',4'-dihydro-2,3'-biquinolin-4'-one
  参考文献：
  名称：

  Investigation of 2,3'-Biquinolyl. 11. Regioselectivity in the Hydroxylation of 1-Alkyl-3-(2-quinolyl)quinolinium Halides

  摘要：

  DOI：

  10.1023/a:1012403725287

文献信息

• 3-Substituted biquinolinium inhibitors of AraC family transcriptional activator VirF from S. flexneri obtained through in situ chemical ionization of 3,4-disubstituted dihydroquinolines
  作者：Prashi Jain、Jiaqin Li、Patrick Porubsky、Benjamin Neuenswander、Susan M. Egan、Jeffrey Aubé、Steven Rogers

  DOI：10.1039/c4ra08384a

  日期：——

  During a structure–activity relationship optimization campaign to develop an inhibitor of AraC family transcriptional activators, we discovered an unexpected transformation of a previously reported inhibitor that occurs under the assay conditions. Once placed in the assay media, the 3,4-disubstituted dihydroquinoline core of the active analogue rapidly undergoes a decomposition reaction to a quaternary 3-substituted biquinolinium. Further examination established an SAR for this chemotype while also demonstrating its resilience to irreversible binding of biologically relevant nucleophiles.

  在一次结构-活性关系优化活动中，旨在开发AraC家族转录激活因子的抑制剂，我们发现了一个意外的转化，发生在之前报告的抑制剂在检测条件下。一旦置于检测介质中，活性类似物的3,4-双取代二氢喹啉核心迅速发生分解反应，生成四取代的3-取代双喹啉离子。进一步的研究建立了该化学类型的SAR，同时也展示了其对生物相关亲核体不可逆结合的抗性。
• Investigations on 2,3′-biquinolines. 18. New convenient one-pot synthesis of 1′-alkyl-1′,4′-dihydro-2,3′-biquinolyl-4′-thiones and their conversion into 1′-alkyl-1′,4′-dihydro-2,3′-biquinolyl-4′-ones
  作者：D. V. Moiseev、N. V. Demidova、V. I. Goncharov、A. V. Aksenov

  DOI：10.1007/s10593-006-0047-9

  日期：2006.1
• Investigations on 2,3′-Biquinoline. 17. Regioselectivity of the Halogenation of 2,3′-Biquinoline Derivatives
  作者：N. V. Demidova、N. Ts. Karaivanov、V. I. Goncharov、A. V. Aksenov

  DOI：10.1007/s10593-005-0297-y

  日期：2005.9
• Investigations of 2,3′-biquinolines 23. Synthesis of 1′-R-1′,4′-dihydro-2,3′-biquinolin-4′-ones by Claisen condensation
  作者：T. P. Glushenko、V. I. Goncharov、A. V. Aksenov

  DOI：10.1007/s10593-008-0046-0

  日期：2008.3

  A method has been developed for the synthesis of 1'-R-1',4'-dihydro-2,3'-biquinolin-4'-ones based on the interaction of quinaldine with N-alkyl-N-formylanthranilic acid methyl esters under the conditions of the Claisen condensation.
• INHIBITING MICROBIAL INFECTIONS
  申请人：Egan Susan M.

  公开号：US20140088144A1

  公开（公告）日：2014-03-27

  A method of inhibiting a microbial infection can include: providing a compound of the invention or prodrugs or pharmaceutically acceptable salts thereof; and administering the compound to a subject in a therapeutically effective amount to inhibit the microbial infection. The therapeutically effective amount can be sufficient to inhibit a biological activity of a transcriptional activator of the microbe. The inhibited transcriptional activator is an AraC bacterial transcriptional activator. The AraC bacterial transcriptional activator can be RhaS, RhaR, Rns, or VirF. The microbe can be selected from Vibrio, Pseudomonas , Enterotoxigenic E. coli , and Shigella.