(E)-1-(4-fluorophenyl)-3-(thiophen-2-yl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(4-fluorophenyl)-3-(thiophen-2-yl)prop-2-en-1-one
• 英文别名: (2E)-1-(4-fluorophenyl)-3-(thiophen-2-yl)prop-2-en-1-one；(E)-1-(4-fluorophenyl)-3-thiophen-2-ylprop-2-en-1-one
• 化学式: C₁₃H₉FOS
• mdl: MFCD00743735
• 分子量: 232.278
• InChiKey: IBVXMMKEECGSBJ-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-fluorophenyl)-3-(thiophen-2-yl)prop-2-en-1-one 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 2-(3-(4-flurophenyl)-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one
  参考文献：
  名称：

  Discovery and modification of sulfur-containing heterocyclic pyrazoline derivatives as potential novel class of β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors

  摘要：

  A series of sulfur-containing heterocyclic pyrazoline derivatives (C1-C18; D1-D9) have been synthesized and purified (all are new except one) to be screened for FabH inhibitory activity. Compound C14 showed the most potent biological activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis (MIC values: 1.56-3.13 mu g/mL), being comparable with the positive control, while D6 performed the best in the thiazolidinone series (MIC values: 3.13-6.25 mu g/mL). They also demonstrated strong broad-spectrum antimicrobial activity. Compounds C14 and D6 exhibited the most potent E. coli FabH inhibitory activity with IC50 of 4.6 and 8.4 mu M, respectively, comparable with the positive control DDCP (IC50 = 2.8 mu M). Docking simulation was performed to position compound C14 and D6 into the E. coli FabH structure active site to determine the probable binding model. The structurally modification of previous compounds and the attempt in innovative target have brought a positive progress. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.05.091
• 作为产物：
  描述：

  2-噻吩甲醛 、 4-氟苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以94%的产率得到(E)-1-(4-fluorophenyl)-3-(thiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  通过Ru（II）催化合成三取代和四取代的吡唑：分子内好氧氧化C–N偶联

  摘要：

  已经开发出了空前的钌（II）催化的分子内氧化C-N偶联方法，可以轻松合成各种具有合成挑战性的三取代和四取代的吡唑。在该转化中，将氧气用作氧化剂。该反应显示出优异的反应性，官能团耐受性和高产率。

  DOI：

  10.1021/ol3022353

文献信息

• Synthesis and Anti-Bacterial Activity of Some Heterocyclic Chalcone Derivatives Bearing Thiofuran, Furan, and Quinoline Moieties
  作者：Chang-Ji Zheng、Sheng-Ming Jiang、Zhen-Hua Chen、Bai-Jun Ye、Hu-Ri Piao

  DOI：10.1002/ardp.201100005

  日期：2011.10

  36 Novel heterocyclic chalcone derivatives were synthesized and tested for their anti‐bacterial activity. Some compounds presented good anti‐microbial activities against Gram‐positive bacteria (including the multidrug‐resistant clinical isolates). This class of compounds presented high potency against Streptococcus mutans, among which the derivatives F2 with an MIC of 2 µg/mL was as active as the standard

  合成了 36 种新型杂环查耳酮衍生物并测试了它们的抗菌活性。一些化合物对革兰氏阳性菌（包括耐多药临床分离株）具有良好的抗菌活性。这类化合物对变形链球菌表现出高效能，其中MIC为2 µg/mL的衍生物F2与标准药物（诺氟沙星）活性相同，但活性低于苯唑西林。所有化合物在 64 µg/mL 时均不抑制革兰氏阴性菌（大肠杆菌 CCARM 1924 或大肠杆菌 CCARM 1356）的生长。
• Synthesis and structural elucidation of pyrimido-[1,2-<i>a</i>]benzimidazoles and fused derivatives. i. dihydropyrimido[1,2-<i>a</i>]benzimidazoles
  作者：Dalai Abou El Ella、Edith Gößnitzer、Winfried Wendelin

  DOI：10.1002/jhet.5570330228

  日期：1996.3

  The condensation of 2-benzimidazolarnine (4, BIA) with α,β-unsaturated ketones 1 affords, according to Desenko, Orlov et al. [12,13], 1,4-dihydropyrimido[1,2-a]benzimidazoles (1,4-DHPBI, 5I). However, the described ring closure reactions could a priori also yield isomeric 1,2-DHPBI 8I or tautomers of DHPBIs 5I and 8I. An unequivocal proof for the postulated structures 5I was not presented. We prepared

  根据Desenko，Orlov等人的说法，2-苯并咪唑氮丙氨酸（4，BIA）与α，β-不饱和酮1的缩合反应。[12，13]，1，4-二氢嘧啶基[1，2- a ]苯并咪唑（1，4- DHPBI，5I）。然而，所描述的闭环反应也可以事先产生异构的1,2- DHPBI 8I或DHPBI 5I和8I的互变异构体。没有提出假定结构5I的明确证据。我们制备，如所描述的[12,13]，BIA -chalcone-和BIA -benzalacetone缩合物X和Y，5A，电子或8a，e，以及它们的盐酸盐。一维和二维高分辨率NMR分析表明，仅生成了异构体5a，e和盐5a，e ·HCl。在DMSO-d 6中，这些异构体仅以1,4-二氢互变异构体5a，eI和5a，eI ·HCl的形式存在。在三氟乙酸3,4-二氢互变异构体5α，EIII ·CF 3 COOH除了互变异构体的图5a，EI·CF 3 COOH（≈1：
• Synthesis of Tri- and Tetrasubstituted Pyrazoles via Ru(II) Catalysis: Intramolecular Aerobic Oxidative C–N Coupling
  作者：Jiantao Hu、Shi Chen、Yonghui Sun、Jing Yang、Yu Rao

  DOI：10.1021/ol3022353

  日期：2012.10.5

  An unprecedented ruthenium(II)-catalyzed intramolecular oxidative C–N coupling method has been developed for the facile synthesis of a variety of synthetically challenging tri- and tetrasubstituted pyrazoles. Dioxygen gas is employed as the oxidant in this transformation. The reaction demonstrates excellent reactivity, functional group tolerance, and high yields.

  已经开发出了空前的钌（II）催化的分子内氧化C-N偶联方法，可以轻松合成各种具有合成挑战性的三取代和四取代的吡唑。在该转化中，将氧气用作氧化剂。该反应显示出优异的反应性，官能团耐受性和高产率。
• One-pot synthesis of 4,6-diaryl-3-cyanopyridine-2(1H)-thiones and their transformation to substituted thieno[2,3-b;4,5-b]dipyridines and pyrido[3",2":4,5]thieno[3,2-d]pyrimidines
  作者：A. M. Shestopalov、K. G. Nikishin、A. V. Gromova、L. A. Rodinovskaya

  DOI：10.1023/b:rucb.0000011879.89900.1f

  日期：2003.10

  one step by the reaction of elemental sulfur, malononitrile, and 2-aryl-1-aroylethylenes in the presence of excess triethylamine. The products were used in one-pot syntheses of substituted thieno[2,3-b;4,5-b]dipyridines and pyrido[3",2":4,5]thieno[3,2-d]pyrimidines.

  摘要 4,6-二芳基-3-氰基吡啶-2(1H)-硫酮在过量三乙胺存在下，由元素硫、丙二腈和2-芳基-1-芳酰基乙烯反应一步合成。产物用于取代噻吩并[2,3-b;4,5-b]二吡啶和吡啶并[3",2":4,5]噻吩并[3,2-d]嘧啶的一锅合成。
• Synthesis, biological activities, and docking study of novel chalcone‐pleuromutilin derivatives
  作者：Chuan Xie、Siyu Zhang、Wei Zhang、Chunxia Wu、Can Yong、Yuhao Sun、Zhengxing Zeng、Qian Zhang、Zixin Huang、Tian Chen、Yuanyuan Zhang

  DOI：10.1111/cbdd.13692

  日期：2020.8

  discover novel antibiotics. The diterpene natural pleuromutilin is a prominent candidate for its special mode of action by inhibiting protein synthesis. In this study, a series of novel pleuromutilin derivatives with chalcone moiety was designed and synthesized, and their antibacterial activities were assessed in vitro. As suggested from the results, most of compounds exhibited potent activities against

  这些天，抗生素抗性问题变得越来越严重，解决该问题的可行解决方案是开发和发现新型抗生素。二萜天然截短侧耳素因其通过抑制蛋白质合成的特殊作用方式而成为重要候选者。在这项研究中，设计和合成了一系列具有查耳酮部分的截短侧耳素新衍生物，并在体外评估了它们的抗菌活性。结果表明，大多数化合物对两种耐甲氧西林的金黄色葡萄球菌均具有有效的活性。（MRSA）ATCC 33591和43300。随后对查尔酮结构，氮杂环衍生物进行了进一步修饰，然后进行了评估，并报道了其对测试菌株的有效活性。进行了初步的对接研究，以探索目标分子与结合位点之间的相互作用。