(2E)-1-(thiophen-2-yl)-3-[4-(trifluoromethyl) phenyl] prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-1-(thiophen-2-yl)-3-[4-(trifluoromethyl) phenyl] prop-2-en-1-one
• 英文别名: 1-Thiophen-2-yl-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one
• 化学式: C₁₄H₉F₃OS
• 分子量: 282.286
• InChiKey: FCEHZESLNMUDKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-1-(thiophen-2-yl)-3-[4-(trifluoromethyl) phenyl] prop-2-en-1-one 、 肼甲酰亚胺酰胺一氯化氢 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以62%的产率得到5-(4-trifluoromethylphenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride
  参考文献：
  名称：

  Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines

  摘要：

  3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides were efficiently prepared through a cyclocondensation of thiophenylchalcones with aminoguanidine hydrochloride under ultrasonic conditions in the presence of KOH and ethanol as a green solvent in short reaction times (15-35 min) and good yields (62-95%). All compounds produced were evaluated against the human Jurkat and RS4; 11 acute lymphoblastic leukemia cell lines of T- and B-cell origin, respectively, and the K562 myelogenous leukemia cell line. Six compounds presented half maximal inhibitory concentration (IC50) values around 15 mu mol L-1 and five compounds presented IC50 values around 40 mu mol L-1 for at least one of the three cell lines analyzed. One compound was not significantly cytotoxic, presenting IC50 value > 100 mu mol L- 1.

  DOI：

  10.5935/0103-5053.20160166
• 作为产物：
  描述：

  2-乙酰基噻吩 、 对三氟甲基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (2E)-1-(thiophen-2-yl)-3-[4-(trifluoromethyl) phenyl] prop-2-en-1-one
  参考文献：
  名称：

  合成4-4- [5-芳基-3-（噻吩-2-基）-4-5-二氢-1H-吡唑-1-基]苯磺酰胺类化合物对乙酰胆碱酯酶，碳酸酐酶I和II的合成，分子建模和生物学评估

  摘要：

  在这项研究中，合成了4- [5-芳基-3-（噻吩-2-基）-4,5-二氢-1 H-吡唑-1-基]苯磺酰胺，并对AChE，hCA I和AChE具有抑制作用。 hCA II进行了评估。朝向hCA I的化合物的K i值在24.2±4.6-49.8±12.8 n m的范围内，而朝向hCA II的K i值在37.3±9.0-65.3±16.7 n m的范围内。两种同工酶的乙酰唑酰胺的K i值分别为282.1±19.7 n m和103.60±27.6 n m。化合物抑制的AChE与ķ我在22.7±10.3-109.1±27.0 n中的范围米，而他克林具有ķi值为66.5±13.8 n m。还进行了M06-L / 6-31 + G（d，p）// AM1水平的电子结构计算和分子对接研究，以启发抑制机理并支持实验结果。通过分子特性计算获得的结果表明，这些化合物符合药物样特性。在这项研究中获得的实验和计算结果可能有助于设计针对hCA

  DOI：

  10.1111/cbdd.13149

文献信息

• Synthesis, Cyclooxygenase Inhibition, Anti-Inflammatory Evaluation, and Ulcerogenic Liability of New 1,3,5-Triarylpyrazoline Derivatives Possessing a Methanesulfonyl Pharmacophore
  作者：Khaled R. A. Abdellatif、Wael A. A. Fadaly、Amany A. Azouz

  DOI：10.1002/ardp.201600145

  日期：2016.10

  A new series of 1,3,5‐triarylpyrazolines 13a–l was synthesized and all prepared compounds were evaluated for their in vitro COX‐1/COX‐2 inhibitory activity and in vivo anti‐inflammatory activity. All test compounds were more selective for the COX‐2 isozyme and showed good in vivo anti‐inflammatory activity. Compound 13h was the most COX‐2 selective compound (COX‐2 selectivity index (SI) = 10.23) and

  合成了一系列新的 1,3,5-三芳基吡唑啉 13a-l，并评估了所有制备的化合物的体外 COX-1/COX-2 抑制活性和体内抗炎活性。所有测试化合物对 COX-2 同工酶的选择性更高，并显示出良好的体内抗炎活性。与塞来昔布（COX-2 SI = 9.29 和ED50 = 81.4 µmol/kg)。与阿司匹林 (UI = 2.33) 相比，所有筛选化合物的致溃疡性 (溃疡指数 (UI) = 0.33–1.33) 均低于塞来昔布 (UI = 0.33)。
• Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1,3,5-triarylpyrazoline and 1,5-diarylpyrazole derivatives as selective COX-2 inhibitors
  作者：Khaled R.A. Abdellatif、Eman K.A. Abdelall、Wael A.A. Fadaly、Gehan M. Kamel

  DOI：10.1016/j.bmcl.2015.11.105

  日期：2016.1

  Two new series of 1,3,5-triarylpyrazolines 10a-m and 1,5-diarylpyrazoles 14a-d were synthesized. All prepared compounds were evaluated for their in vitro COX-1/COX-2 inhibitory activity and the in vivo anti-inflammatory activity. All compounds were more selective for COX-2 isozyme and showed good in vivo anti-inflammatory activity. Compound 10k was the most COX-2 selective compound (S.I. = 5.91) and the most potent anti-inflammatory derivative (ED50 = 99 mu mol/kg) which is approximately five folds more potent than ibuprofen (ED50 = 499 mu mol/kg) and had half potency of celecoxib (ED50 = 47 mu mol/kg). All compounds were less ulcerogenic (Ulcer Indexes = 1.20-5.00) than ibuprofen (Ulcer Index = 20.25) and comparable to celecoxib (Ulcer Index = 2.90). (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis, molecular modeling, and biological evaluation of 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1<i>H</i>-pyrazol-1-yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes
  作者：Cem Yamali、Halise Inci Gul、Abdulilah Ece、Parham Taslimi、Ilhami Gulcin

  DOI：10.1111/cbdd.13149

  日期：2018.4

  In this study, 4‐[5‐aryl‐3‐(thiophen‐2‐yl)‐4,5‐dihydro‐1H‐pyrazol‐1‐yl] benzenesulfonamides were synthesized, and inhibition effects on AChE, hCA I, and hCA II were evaluated. Ki values of the compounds toward hCA I were in the range of 24.2 ± 4.6‐49.8 ± 12.8 nm, while they were in the range of 37.3 ± 9.0‐65.3 ± 16.7 nm toward hCA II. Ki values of the acetazolamide were 282.1 ± 19.7 nm and 103.60 ± 27

  在这项研究中，合成了4- [5-芳基-3-（噻吩-2-基）-4,5-二氢-1 H-吡唑-1-基]苯磺酰胺，并对AChE，hCA I和AChE具有抑制作用。 hCA II进行了评估。朝向hCA I的化合物的K i值在24.2±4.6-49.8±12.8 n m的范围内，而朝向hCA II的K i值在37.3±9.0-65.3±16.7 n m的范围内。两种同工酶的乙酰唑酰胺的K i值分别为282.1±19.7 n m和103.60±27.6 n m。化合物抑制的AChE与ķ我在22.7±10.3-109.1±27.0 n中的范围米，而他克林具有ķi值为66.5±13.8 n m。还进行了M06-L / 6-31 + G（d，p）// AM1水平的电子结构计算和分子对接研究，以启发抑制机理并支持实验结果。通过分子特性计算获得的结果表明，这些化合物符合药物样特性。在这项研究中获得的实验和计算结果可能有助于设计针对hCA
• Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1<i>H</i>-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
  作者：Eric F. S. dos Santos、Nathália M. Cury、Tainara A. do Nascimento、Cristiano Raminelli、Gleison A. Casagrande、Claudio M. P. Pereira、Euclésio Simionatto、José A. Yunes、Lucas Pizzuti

  DOI：10.5935/0103-5053.20160166

  日期：——

  3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides were efficiently prepared through a cyclocondensation of thiophenylchalcones with aminoguanidine hydrochloride under ultrasonic conditions in the presence of KOH and ethanol as a green solvent in short reaction times (15-35 min) and good yields (62-95%). All compounds produced were evaluated against the human Jurkat and RS4; 11 acute lymphoblastic leukemia cell lines of T- and B-cell origin, respectively, and the K562 myelogenous leukemia cell line. Six compounds presented half maximal inhibitory concentration (IC50) values around 15 mu mol L-1 and five compounds presented IC50 values around 40 mu mol L-1 for at least one of the three cell lines analyzed. One compound was not significantly cytotoxic, presenting IC50 value > 100 mu mol L- 1.