1-[2-phenyl-2-oxoethyl]-4-methylquinolin-1-ium bromide | 136714-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-phenyl-2-oxoethyl]-4-methylquinolin-1-ium bromide
• 英文别名: 4-methyl-1-phenacyl-quinolinium bromide；2-(4-methylquinolin-1-ium-1-yl)-1-phenylethanone;bromide
• CAS: 136714-38-0
• 化学式: Br*C₁₈H₁₆NO
• 分子量: 342.235
• InChiKey: QXOQPNUCSQCQIK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[2-phenyl-2-oxoethyl]-4-methylquinolin-1-ium bromide 、 丁炔二酸二甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 dimethyl 1-benzoyl-5-methylpyrrolo[1,2-a]quinoline-2,3-dicarboxylate
  参考文献：
  名称：

  Cytotoxicity and Antimycobacterial Properties of Pyrrolo[1,2-a]quinoline Derivatives: Molecular Target Identification and Molecular Docking Studies

  摘要：

  一系列乙基1-(取代苯甲酰基)-5-甲基吡咯并[1,2-a]喹啉-3-羧酸酯4a-f和二甲基1-(取代苯甲酰基)-5-甲基吡咯并[1,2-a]喹啉-2,3-二羧酸酯4g-k已经合成，并通过雷萨祖林微孔板法（REMA）评估其对H37Rv（美国类型培养物收藏中心（ATCC）菌株25177）和结核分枝杆菌多药耐药（MDR）菌株的抗结核活性。这些化合物的分子靶标鉴定也通过计算方法进行。所有测试化合物对H37Rv表现出8-128 µg/mL范围内的抗结核（TB）活性。测试化合物二甲基-1-(4-氟苯甲酰基)-5-甲基吡咯并[1,2-a]喹啉-2,3-二羧酸酯4j在8和16 µg/mL浓度下分别显示出对H37Rv和结核分枝杆菌多药耐药菌株最有前景的抗TB活性。药代动力学性质的体外评估表明大多数化合物具有整体药物样性。还进行了对接研究，以调查这些化合物与靶蛋白的结合亲和力和相互作用。

  DOI：

  10.3390/antibiotics9050233
• 作为产物：
  描述：

  4-甲基喹啉 、 2-溴苯乙酮 以 neat (no solvent) 为溶剂， 反应 4.0h， 生成 1-[2-phenyl-2-oxoethyl]-4-methylquinolin-1-ium bromide
  参考文献：
  名称：

  Copper acetate monohydrate: a cheap but efficient oxidant for synthesizing multi-substituted indolizines from pyridinium ylides and electron deficient alkenes

  摘要：

  我们报道了一种高度实用的、一步合成多取代吲哚嗪的方法，该方法使用α-卤代羰基化合物、吡啶和缺电子烯烃，在醋酸铜一水合物和醋酸钠的DMF溶液中进行。在标准反应条件下，各种功能团（包括醛）都能耐受。我们提供了36个例子，吲哚嗪的产率从中等到高。此外，通过这种方法还能在克级规模上制备多取代吲哚嗪。

  DOI：

  10.1039/c2ra21213g

文献信息

• Substituted 1-benzoyl-3-cyano-pyrrolo [1,2-a] quinolines and analogs as activators of caspases and inducers of apoptosis
  申请人：Cai Xiong Sui

  公开号：US20050014759A1

  公开（公告）日：2005-01-20

  The present invention is directed to substituted 1-benzoyl-3-cyano-pyrrolo[1,2-a]quinolines and analogs thereof, represented by the general Formula I: wherein R 1 —R 8 , L, Q, dash line and Ar are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代的1-苯甲酰基-3-氰基-吡咯并[1,2-a]喹啉及其类似物，由通用式I表示： 其中R1-R8，L，Q，虚线和Ar在此定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生未受控制的异常细胞生长和扩散的细胞死亡。
• Synthesis and characterization of pyrrolo[1,2-a]quinoline derivatives for their larvicidal activity against Anopheles arabiensis
  作者：Vijayakumar Uppar、Sandeep Chandrashekharappa、Katharigatta N. Venugopala、Pran Kishore Deb、Supratik Kar、Osama I. Alwassil、Raquel M. Gleiser、Daniel Garcia、Bharti Odhav、Mahendra K. Mohan、Rashmi Venugopala、Basavaraj Padmashali

  DOI：10.1007/s11224-020-01516-w

  日期：2020.8

  synthesized compounds 2a-k were screened for their larvicidal activity against Anopheles arabiensis using a standard World Health Organization larvicidal assay; compounds 2b and 2e at 8.12 and 9.2 μM exhibited the highest larval mortality at 78 and 89%, respectively, when compared with the negative control acetone, and it demonstrated less activity, which was similar to the positive control, temephos

  某些四氢吡啶并 [1,2-a] 喹啉和吡咯并喹啉同系物已显示出多种生物活性，例如抗微生物剂、作物保护剂、利尿剂、抗氧化剂、抗凝剂和抗疟疾活性。牢记这一观察，我们设想合成和表征一系列新型 1-(取代苯甲酰基)-5-甲基吡咯并[1,2-a]喹啉-3-羧酸乙酯和 1-(取代苯甲酰基)-5-二甲酯甲基吡咯并[1,2-a]喹啉-2,3-二羧酸酯(2a-k)。通过在室温下分别在丙酮中搅拌来匹啶与不同的苯甲酰溴，来获得来匹啶的季盐，例如 1-[2-(取代苯基)-2-氧乙基]-4-甲基喹啉-1-溴化鎓(1a-f)。然后分别用缺电子丙炔酸乙酯和二甲基丁二酸丁酯（1a-f）分别处理这些来比丁（1a-f）的季盐，在无水碳酸钾和二甲基甲酰胺(DMF)溶剂存在下，得到1-(取代苯甲酰基)-5-甲基吡咯并[1,2-a]喹啉-3-羧酸乙酯和1-(取代苯甲酰基)-5-甲基吡咯并[ 1,2-a]喹啉-2,3-二羧酸盐，分别为
• One-pot synthesis of indolizine via 1,3-dipolar cycloaddition using a sub-equivalent amount of K₂Cr₂O₇ as an efficient oxidant under base free conditions
  作者：Chao Wang、Huayou Hu、Juanfang Xu、Weiqiu Kan

  DOI：10.1039/c5ra06019b

  日期：——

  X = Cl or Br; EWG₁, EWG₂ = electron withdrow group, one-pot reaction, 29 examples, yields from moderate to high, gram scale-up potential confirmed.

  X = 氯或溴；EWG1，EWG2 = 电子吸引基团，一锅法反应，29个例子，产率从中等到高，克级放大潜力得到确认。
• Discovery of 1-benzoyl-3-cyanopyrrolo[1,2-a]quinolines as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 2: Structure–activity relationships of the 4-, 5-, 6-, 7- and 8-positions
  作者：William Kemnitzer、Jared Kuemmerle、Songchun Jiang、Nilantha Sirisoma、Shailaja Kasibhatla、Candace Crogan-Grundy、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2009.05.012

  日期：2009.7

  As a continuation of our efforts to discover and develop the apoptosis inducing 1-benzoyl-3-cyanopyrrolo[1,2-a] quinolines as potential anticancer agents, we explored substitutions at the 4-, 5-, 6-, 7- and 8-positions of pyrrolo[1,2-a] quinoline. SAR studies showed that substitution at the 6- position by a small group such as Cl resulted in potent compounds. Substitutions at the 5- and 8-positions were tolerated while substitutions at the 4- and 7- position led to inactive compounds. Several compounds, including 2c, 3a, 3b and 3f, were found to be highly active against human breast cancer cells T47D with EC50 values of 0.053-0.080 mu M, but much less active against human colon cancer cells HCT116 and hepatocellular carcinoma cancer cells SNU398 in the caspase activation assay. Compound 3f also was found to be highly active with a GI(50) value of 0.018 mu M against T47D cells in a growth inhibition assay. (C) 2009 Elsevier Ltd. All rights reserved.
• Regioselectivity in the reaction of azinium salts and ylides with tetracyanoethylene
  作者：A. M. Shestopalov、I. A. Aitov、Yu. A. Sharanin、V. P. Litvinov

  DOI：10.1007/bf00961312

  日期：1991.6

  The reactions of pyridinium, picolinium, and quinolinium salts and ylides with tetracyanoethylene have been found to be regioselective. Reaction of azinium salts with tetracyanoethylene in aqueous methanol affords azinium tricyanoethylenolates, but pyridinium ylides react differently, with the highly stereoselective formation of the Z-isomers of 3-aroyl-3-(R-1-pyridinio)-1,1,2-tricyano-2-propen-1-ides, which are 1,4-ylides with maximum charge separation.