1-(4-bromophenyl)-3-(2-chloroquinolin-3-yl)prop-2-en-1-one | 177841-09-7

• 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: 1-(4-bromophenyl)-3-(2-chloroquinolin-3-yl)prop-2-en-1-one
• 英文别名: 3-(2-chloroquinolin-3-yl)-1-(4-bromophenyl)prop-2-en-1-one
• CAS: 177841-09-7
• 化学式: C₁₈H₁₁BrClNO
• 分子量: 372.648
• InChiKey: NLWSEBZEXGMGHF-UHFFFAOYSA-N

物化性质

• 熔点：
  166-170 °C(Solv: methanol (67-56-1))
• 沸点：
  514.4±50.0 °C(Predicted)
• 密度：
  1.519±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-3-(2-chloroquinolin-3-yl)prop-2-en-1-one 在 盐酸羟胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2-chloro-3-[3-(4-bromophenyl)-4,5-dihydroisoxazol-5-yl]quinoline
  参考文献：
  名称：

  An efficient one-pot synthesis and photoinduced DNA cleavage studies of 2-chloro-3-(5-aryl-4,5-dihydroisoxazol-3-yl)quinolines

  摘要：

  4,5-Dihydroisoxazoles continue to attract considerable interest due to their wide spread biological activities. Here, we identify an efficient protocol for the preparation of 4,5-dihydroisoxazoles (2-isaxazolines) (4a-g) from quinolinyl chalcones. The nucleolytic activities of synthesized compounds were investigated by agarose gel electrophoresis. All these compounds were showed the remarkable DNA cleavage activity (concentration dependent) with pUC19 DNA at 365 nm UV light. The DNA cleavage activity was significantly enhanced by the presence of iminyl and carboxy radicals of DIQ. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.034
• 作为产物：
  描述：

  N-乙酰苯胺 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 1-(4-bromophenyl)-3-(2-chloroquinolin-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  带有吡唑啉和吡啶类似物的新型喹啉衍生物的合成和抑菌活性

  摘要：

  本研究符合某些含有（5-（2-氯喹啉-3-基）-3-（芳基）-4,5-二氢-1 H-吡唑-1-基）（吡啶-结合了不同的生物活性杂环（例如喹啉，吡唑啉和吡啶衍生物）的4-yl）methanenes（4a-o）部分。为了确定本文报道的化合物是基于IR，1 H NMR，13 C NMR和质谱数据，并筛选了相同的化合物对四种细菌（金黄色葡萄球菌，化脓性链球菌，大肠埃希氏菌，铜绿假单胞菌）和三种真菌（以氨苄青霉素和灰黄霉素为标准药物的白色念珠菌，黑曲霉，克拉维斯曲霉。使用MTT比色测定法（HeLa细胞系）进行细胞毒性研究。在筛选出的化合物中，4e，4f和4n表现出最强的抗菌活性，而化合物4d和4g表现出对真菌菌株最有活性。结果表明，化合物4o对所有微生物菌株均具有显着活性。从SAR研究的观点来看，观察到吸电子基团的存在显着增强了合成化合物的抗菌活性。另外，对HeLa细胞的MTT初步细胞毒性研究表明，有效的4e

  DOI：

  10.1007/s00044-016-1732-6

文献信息

• Synthesis and molecular docking studies of quinoline derivatives as HIV non-nucleoside reverse transcriptase inhibitors
  作者：Nivedita BHARDWAJ、Diksha CHOUDHARY、Akashdeep PATHANIA、Somesh BARANWAL、Pradeep KUMAR

  DOI：10.3906/kim-2004-14

  日期：——

  Quinoline moiety is an important scaffold in the field of drug discovery and drug development, with a wide range of pharmacological activities. Quinoline derivatives are potent inhibitors for reverse transcriptase, which is responsible for the conversion of single-stranded viral RNA into double-stranded viral DNA.In the present study, we have designed and synthesized 2 series, namely pyrazoline and pyrimidine containing quinoline derivatives as non nucleoside reverse transcriptase inhibitors (NNRTIs). Eleven compounds were synthesized and characterized by 1H and 13C NMR and mass spectrophotometry. The synthesized compounds were also docked on an HIV reverse transcriptase binding site (PDB: 4I2P); most of these compounds showed good binding interactions with the active domain of the receptor. Most of the compounds displayed a docking score higher than those of standard drugs. Among the synthesized quinoline derivatives, compound 4 exhibited the highest docking score (-10.675).

  喹啉部分是药物发现和药物开发领域中的重要支架，具有广泛的药理活性。喹啉衍生物是逆转录酶的强效抑制剂，这种酶负责将单链病毒RNA转化为双链病毒DNA。在本研究中，我们设计并合成了两系列具有喹啉骨架的吡唑啉和嘧啶衍生物，作为非核苷类逆转录酶抑制剂（NNRTIs）。我们合成了11种化合物并通过1H和13C核磁共振以及质谱光谱法进行了表征。这些合成的化合物还被对接到了HIV逆转录酶的结合位点（PDB: 4I2P）；这些化合物中的大多数与受体的活性域显示出良好的结合相互作用。大部分化合物的对接分数高于标准药物。在合成的喹啉衍生物中，化合物4显示出最高的对接分数（-10.675）。
• Synthesis, characterization, and biological applications of pyrazole moiety bearing osmium(IV) complexes
  作者：Bharat H. Pursuwani、Bhupesh S. Bhatt、Dilip B. Raval、Vasudev R. Thakkar、Jyoti Sharma、Chandramani Pathak、Mohan N. Patel

  DOI：10.1080/15257770.2021.1921795

  日期：2021.6.3

  Abstract Osmium (IV) complexes with pyrazole nucleus containing ligands were synthesized. Os(IV) compounds were characterized using ESI-MS, ICP-OES, IR spectroscopy, electronic spectroscopy, conductance, and magnetic measurements. Whereas, ligands were characterized by heteronuclear spectroscopy, (1H and 13C), IR spectroscopy, and elemental analysis. All the compounds were tested for their potential

  抽象的 合成了含有吡唑核配体的锇（IV）配合物。使用 ESI-MS、ICP-OES、红外光谱、电子光谱、电导和磁测量对 Os(IV) 化合物进行表征。而配体通过异核光谱（ 1 H 和13 C）、红外光谱和元素分析进行​​表征。通过吸收滴定、荧光光谱、粘度测量和对接研究测试了所有化合物与 HS-DNA 相互作用的潜力。使用荧光研究计算猝灭常数和斯特恩沃尔默常数值。研究了合成化合物的体外抑菌和细胞毒活性。所有合成的复合物的癌细胞系研究均在人肺癌细胞（A549）上进行。 Supplemental data for this article is available online at https://doi.org/10.1080/15257770.2021.1921795 .
• Efficient one pot and chemoselective synthesis of functionalized 3-bromo-4,5-dihydroisoxazole derivatives via 1,3-dipolar cycloaddition reactions of nitrile oxides
  作者：Abdolali Alizadeh、Atefeh Roosta、Reza Rezaiyehrad、Mohammadreza Halvagar

  DOI：10.1016/j.tet.2017.10.003

  日期：2017.11

  A novel, metal-free and chemoselective approach for the synthesis of 4,5-dihydroisoxazole derivatives has been developed by the reaction of readily accessible starting materials including 4-oxo-4H-chromene-3-carbaldehyde, 1-phenyl-2-(1,1,1-triphenyl-λ5-phosphanylidene)ethan-1-one and dibromoformaldoxime under mild conditions in the presence of KHCO3.

  通过易于获得的起始原料（包括4-氧代-4 H-色烯-3-甲醛，1-苯基-2-基）的反应，开发了一种新颖的，无金属且化学选择性的合成4,5-二氢异恶唑衍生物的方法（1,1,1-三苯基λ 5 -phosphanylidene）乙烷-1-酮在KHCO存在温和的条件下和二溴甲醛肟3。
• Benign methodology and improved synthesis of 5-(2-chloroquinolin-3-yl)-3-phenyl-4,5-dihydroisoxazoline using acetic acid aqueous solution under ultrasound irradiation
  作者：Vandana Tiwari、Ali Parvez、Jyotsna Meshram

  DOI：10.1016/j.ultsonch.2010.12.003

  日期：2011.9

  In the present paper, we have executed the synthesis of substituted 5-(2-chloroquinolin-3-yl)-3-pheny-14,5-dihydroisoxazolines via the reactions of substituted 3-(2-chloroquinolin-3-yl)-1-phenylprop-2-en-1-ones with hydroxylamine hydrochloride and sodium acetate in aqueous acetic acid solution in 72-90% yields at room temperature under ultrasound irradiation. This method provides several advantages such as operational simplicity, higher yield, safety and environment friendly protocol. The resulting substituted isoxazolines were characterized on the basis of H-1 NMR, C-13 NMR, IR, elemental analysis, and mass spectral data. (C) 2010 Elsevier B.V. All rights reserved.
• Efficient Continuous-Flow Synthesis and Evaluation of Anticancer Activity of Novel Quinoline–Pyrazoline Derivatives
  作者：K. Santhosh Kumar、V. Siddaiah、J. D. Lilakar、K. Sunanda、A. Ganesh

  DOI：10.1134/s1070428020110160

  日期：2020.11