6-(dimethylamino)-2-methyl-4(1H)-quinolinone | 501653-44-7

• 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-(dimethylamino)-2-methyl-4(1H)-quinolinone
• 英文别名: 6-dimethylamino-2-methyl-4(1H)-quinolinone；6-dimethylamino-2-methylquinolinone；6-(Dimethylamino)-2-methylquinolin-4-ol；6-(dimethylamino)-2-methyl-1H-quinolin-4-one
• CAS: 501653-44-7；91566-30-2
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: XAWXYXWRJBIQPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  362.4±42.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(dimethylamino)-2-methyl-4(1H)-quinolinone 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 4-Chlor-6-dimethylaminochinaldin
  参考文献：
  名称：

  新型 4-氨基喹啉：结核分枝杆菌烯酰基载体蛋白还原酶的合成、抑制、抗结核活性、SAR 和临床前评价

  摘要：

  在此合成了一系列 4-氨基喹啉，试图优化和研究与 LABIO-17 生物活性相关的结构特征，LABIO-17 是结核分枝杆菌 NADH依赖性烯酰基-酰基载体蛋白还原酶 ( Mt InhA) 抑制剂，先前由虚拟-配体筛选方法。构效关系导致了新型亚微摩尔Mt InhA 抑制剂和强效抗结核药物的产生。与 LABIO-17 相比，先导化合物作为酶抑制剂的效力高 87 倍，对结核分枝杆菌H37Rv 菌株的效力高 32 倍。这些分子对多重耐药菌株也有活性，对哺乳动物细胞没有明显毒性，并显示出良好的体外ADME 概况。此外，这些化合物在结核病 (TB) 感染的细胞内模型中具有活性，没有表现出遗传毒性信号、令人满意的吸收参数并且没有体内急性毒性。最后，用选定的 4-氨基喹啉治疗两周在结核病小鼠模型中产生抑菌作用。总而言之，这些发现表明该化学类别可能为未来开发药物敏感和耐药的结核病治疗提供候选药物。

  DOI：

  10.1016/j.ejmech.2022.114908
• 作为产物：
  描述：

  3-(4-dimethylamino-anilino)-crotonic acid ethyl ester 在 二苯醚 、 联苯 作用下， 生成 6-(dimethylamino)-2-methyl-4(1H)-quinolinone
  参考文献：
  名称：

  Some Displacement Reactions of 4,7-Dichloro-1-methylquinolinium Ion

  摘要：

  DOI：

  10.1021/ja01564a038

文献信息

• 一种喹啉类生物硫醇荧光探针及其制备和应 用
  申请人：贺州学院

  公开号：CN107721922B

  公开（公告）日：2020-05-05

  本发明公开了一种新型喹啉类生物硫醇荧光探针及其制备方法和应用，所述新型喹啉类生物硫醇荧光探针为6‑二甲胺基‑2‑甲基‑4‑喹啉基‑2,4‑二硝基苯磺酸酯，结构式如式(1)：制备方法包括以下步骤：(1)N,N‑二甲基对苯二胺与乙酰乙酸乙酯发生缩合反应，得到6‑二甲胺基‑2‑甲基‑4(1H)‑喹啉酮；(2)步骤(1)所得的6‑二甲胺基‑2‑甲基‑4(1H)‑喹啉酮与2,4‑二硝基苯磺酰氯发生磺酰化反应，得到式(1)所示的化合物。本发明荧光探针分子对生物硫醇的检测表现出较高的选择性和灵敏度。
• 639. A search for new trypanocides. Part II. 4-Amino-6-dialkylaminoquinaldines
  作者：H. Bader

  DOI：10.1039/jr9560003293

  日期：——
• Potent DNA-directed alkylating agents: Synthesis and biological activity of phenyl N-mustard–quinoline conjugates having a urea or hydrazinecarboxamide linker
  作者：Rajesh Kakadiya、Huajin Dong、Amit Kumar、Dodia Narsinh、Xiuguo Zhang、Ting-Chao Chou、Te-Chang Lee、Anamik Shah、Tsann-Long Su

  DOI：10.1016/j.bmc.2010.01.061

  日期：2010.3

  A series of N-mustard-quinoline conjugates bearing a urea or hydrazinecarboxamide linker was synthesized for antitumor evaluation. The in vitro cytotoxicity studies revealed that compounds with hydrazinecarboxamide linkers were generally more cytotoxic than the corresponding urea counterparts in inhibiting human lymphoblastic leukemia and various solid tumor cell growths in culture. The therapeutic efficacy against human tumor xenografts in animal model was studied. It was shown that complete tumor remission in nude mice bearing human breast carcinoma MX-1 xenograft by 17a, i and 18c, d was achieved. In the present study, it was revealed that both linkers are able to lower the chemically reactive N-mustard pharmacophore and thus the newly synthesized conjugates possess a long half-life in rat plasma. Moreover, the new N-mustard derivatives are able to induce DNA cross-linking either by modified comet assay or by alkaline agarose gel shift assay. (C) 2010 Elsevier Ltd. All rights reserved.
• Quinoline-based fluorescent probe for ratiometric detection of hydrogen peroxide in aqueous solution
  作者：Yuan-Yu Qian、Lin Xue、De-Xin Hu、Guo-Ping Li、Hua Jiang

  DOI：10.1016/j.dyepig.2012.05.013

  日期：2012.11

  A novel quinoline-based fluorescent probe for detecting H2O2 is described. In aqueous solution, the probe exhibits fluorescence emission at 542 nm originating from the monocationic species. The reaction between the probe and H2O2 causes quenching of the emission at 542 nm and simultaneously yields a significant hypsochromic shift of the emission maximum to 480 nm due to the H2O2-triggered boronate cleavage process. Thus, a single-excitation, dual-emission ratiometric measurement with a large blue shift in emission (Delta lambda = 62 nm) and remarkable changes in the ratio (F-480 (nm)/F-542 (nm)) Of the emission intensity (R/R-0 up to 8.3-fold) can be established. Moreover, the probe can also afford high selectivity for detecting H2O2 over other biological reactive oxygen species. (C) 2012 Elsevier Ltd. All rights reserved.