1-Benzyl-2-oxoquinoline-3-carbaldehyde | 114561-33-0

• 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: 1-Benzyl-2-oxoquinoline-3-carbaldehyde
• CAS: 114561-33-0
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: YRSPCRUWAKFSQP-UHFFFAOYSA-N

物化性质

• 沸点：
  443.0±45.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Benzyl-2-oxoquinoline-3-carbaldehyde 在 水 、 正丁胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 1-benzyl-3-((1E,4Z,6E)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trienyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis and anticancer activity of novel curcumin–quinolone hybrids

  摘要：

  A number of new curcumin-quinolone hybrids were synthesised from differently substituted 3-formyl-2-quinolones and vanillin and their in vitro cytotoxicity was determined on a panel of representative cell lines (A549, MCF7, SKOV3 and H460) using MTT assay. The most potent compound 14, was analysed for its mode of action using various cell biology experiments. SKOV3 cells treated with compound 14 showed distorted cell morphology under phase contrast imaging and induction of apoptosis was confirmed by Annexin V/PE assay. Further experiments on generation of reactive oxygen species (ROS) and cell cycle analysis revealed that these hybrids induce apoptosis by ROS generation and arrest cell cycle progression in S and G2/M phase. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.068
• 作为产物：
  描述：

  N-乙酰苯胺 在 水 、 potassium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1-Benzyl-2-oxoquinoline-3-carbaldehyde
  参考文献：
  名称：

  一系列新型的2-氧代喹啉基硫代半脲衍生物的合成，抗疟原虫和抗胰蛋白酶的评估

  摘要：

  本文报道了一系列衍生自2-氧代喹啉骨架的新型硫代半脲（TSC），并已使用标准光谱技术成功合成并表征了目标化合物。评价了合成分子对恶性疟原虫疟原虫（3D7株），布鲁氏锥虫布鲁氏原虫（427株）和HeLa细胞的体外生物学活性。在浓度为20μM时，所有化合物均显示适度或无活性，经常观察到存活率百分数> 50％。除化合物9o外，最终化合物均未对20μM的HeLa细胞表现出细胞毒性作用。

  DOI：

  10.17159/0379-4350/2018/v71a23

文献信息

• Construction of Halofunctionalized Indenes via a Cascade Prins‐Nazarov Cyclization Promoted by Dual Roles of BX ₃
  作者：Sabera Sultana、Yong Rok Lee

  DOI：10.1002/adsc.201901266

  日期：2020.2.21

  carboxaldehydes and boron trihalides (BX3, X=F, Cl, Br, I) is described. A diverse array of halofunctionalized indenes substituted with a heterocycle has been synthesized regioselectively with BX3 as a promotor for the carbocyclization and a source of X− for halogenation. This reaction proceeds via a formal halogenative [4+1] cycloaddition between arylalkynes and carboxaldehydes promoted by boron trihalides to generate

  描述了在特定类别的甲醛和三卤化硼（BX 3，X = F，Cl，Br，I）存在下，各种未活化的芳基炔烃向相应的1H-茚进行卤官能化的过程。用杂环取代的halofunctionalized茚的多样化已经BX区域选择性合成的3作为carbocyclization一个启动子和X的源-用于卤化。该反应通过由三卤化硼促进的芳基炔烃和甲醛之间的正式卤代[4 + 1]环加成反应进行，以生成卤代官能化的茚。卤代官能化的茚的有用性通过它们通过偶联，亲核取代和氧化转化为其他衍生物来证明。
• Synthesis, Antiplasmodial and Antitrypanosomal Evaluation of a Series of Novel 2-Oxoquinoline-based Thiosemicarbazone Derivatives
  作者：Oliver T. Darrel、Siyabonga T. Hulushe、Thanduxolo E. Mtshare、Richard M. Beteck、Michelle Isaacs、Dustin Laming、Heinrich C. Hoppe、Rui W.M. Krause、Setshaba D. Khanye

  DOI：10.17159/0379-4350/2018/v71a23

  日期：——

  Herein a series of novel thiosemicarbazones (TSCs) derived from 2-oxoquinoline scaffold is reported, and the target compounds have been successfully synthesized and characterized using standard spectroscopic techniques. The in vitro biological activities of synthesized molecules were evaluated against Plasmodium falciparum malaria parasites (strain 3D7), Trypanosoma brucei brucei parasites (strain

  本文报道了一系列衍生自2-氧代喹啉骨架的新型硫代半脲（TSC），并已使用标准光谱技术成功合成并表征了目标化合物。评价了合成分子对恶性疟原虫疟原虫（3D7株），布鲁氏锥虫布鲁氏原虫（427株）和HeLa细胞的体外生物学活性。在浓度为20μM时，所有化合物均显示适度或无活性，经常观察到存活率百分数> 50％。除化合物9o外，最终化合物均未对20μM的HeLa细胞表现出细胞毒性作用。
• Novel quinoline–imidazolium adducts via the reaction of 2-oxoquinoline-3-carbaldehyde and quinoline-3-carbaldehydes with 1-butyl-3-methylimidazolium chloride [BMIM][Cl]
  作者：Kenneth K. Laali、Daniel Insuasty、Rodrigo Abonia、Braulio Insuasty、Scott D. Bunge

  DOI：10.1016/j.tetlet.2014.05.094

  日期：2014.7

  A library of hydroxyquinolin-3-ylmethylimidazolium adducts were prepared in high yields from the reaction of [BMIM][Cl] with various substituted quinoline-3-carbaldehydes and 2-oxoquinoline-3-carbaldehydes under mild conditions by using sodium acetate in MeCN under ultrasound irradiation. The use of sodium acetate and imidazolium chloride was crucial for the success of these C C bond forming reactions. Attempted coupling with thiazolium bromide led instead to quinoline-3-carboxylic acid. (C) 2014 Elsevier Ltd. All rights reserved.
• Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids
  作者：Daniel Insuasty、Oscar Vidal、Anthony Bernal、Edgar Marquez、Juan Guzman、Braulio Insuasty、Jairo Quiroga、Laura Svetaz、Susana Zacchino、Gloria Puerto、Rodrigo Abonia

  DOI：10.3390/antibiotics8040239

  日期：——

  a MIC value of 2 µg/mL (5 µM). In addition, hybrid 7h also demonstrated inhibition of Staphylococcus aureus at 20 µg/mL (47 µM). Hybrids 7a and 7b were the most potent against Mycobacterium tuberculosis H37Rv with MIC values of 20 and 10 µg/mL (46 and 24 µM), respectively. The 7b hybrid demonstrated high selectivity in killing S. aureus and M. tuberculosis H37Rv in comparison with mammalian cells (SI

  制备了八种基于喹啉的羟基咪唑杂合体 7a-h，并针对一组临床重要的真菌和细菌病原体（包括分枝杆菌）进行了体外评估。杂合化合物 7c-d 对新型隐球菌表现出显着的抗真菌活性，最低抑菌浓度 (MIC) 值为 15.6 µg/mL。针对其他机会性真菌，例如念珠菌属。和曲霉属，这些杂种的 MIC 值为 62.5 µg/mL。就其抗菌活性而言，所有合成杂合体均表现出对革兰氏阴性菌的抑制作用很小（MIC ≥50 µg/mL），然而，杂合体 7b 在 20 µg/mL 浓度下对肺炎克雷伯菌表现出 >50% 的抑制作用，在 50 µg/mL 浓度下则表现出完全抑制作用毫升。此外，这种杂合体被证明是一种有效的抗葡萄球菌分子，其 MIC 值为 2 µg/mL (5 µM)。此外，hybrid 7h 还表现出在 20 µg/mL (47 µM) 下对金黄色葡萄球菌的抑制作用。杂交种 7a 和 7b 对结核分枝杆菌
• Synthesis and anticancer activity of novel curcumin–quinolone hybrids
  作者：Saiharish Raghavan、Prasath Manogaran、Krishna Kumari Gadepalli Narasimha、Balasubramanian Kalpattu Kuppusami、Palanivelu Mariyappan、Anjana Gopalakrishnan、Ganesh Venkatraman

  DOI：10.1016/j.bmcl.2015.06.068

  日期：2015.9

  A number of new curcumin-quinolone hybrids were synthesised from differently substituted 3-formyl-2-quinolones and vanillin and their in vitro cytotoxicity was determined on a panel of representative cell lines (A549, MCF7, SKOV3 and H460) using MTT assay. The most potent compound 14, was analysed for its mode of action using various cell biology experiments. SKOV3 cells treated with compound 14 showed distorted cell morphology under phase contrast imaging and induction of apoptosis was confirmed by Annexin V/PE assay. Further experiments on generation of reactive oxygen species (ROS) and cell cycle analysis revealed that these hybrids induce apoptosis by ROS generation and arrest cell cycle progression in S and G2/M phase. (C) 2015 Elsevier Ltd. All rights reserved.