(E)-3-(3-hydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one | 21164-27-2

• 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: (E)-3-(3-hydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one
• 英文别名: 3-(3-Hydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one；(E)-3-(3-hydroxyphenyl)-1-thiophen-2-ylprop-2-en-1-one
• CAS: 21164-27-2
• 化学式: C₁₃H₁₀O₂S
• mdl: MFCD08882938
• 分子量: 230.287
• InChiKey: CWGOIPMGZKNLCL-VOTSOKGWSA-N

物化性质

• 熔点：
  141.5-143 °C
• 沸点：
  426.3±45.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-hydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one 在 盐酸 、 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 3-[3-hydroxy-4-(piperidin-1-ylmethyl)phenyl]-1-(thiophen-2-yl)propan-1-one
  参考文献：
  名称：

  Syntheses and in Vitro Antiplasmodial Activity of Aminoalkylated Chalcones and Analogues

  摘要：

  A series of readily synthesized and inexpensive aminoalkylated chalcones and diarylpropane analogues (1-55) were synthesized and tested against chloroquinone-sensitive (D10 and NF54) and -resistant (Dd2 and K1) strains of Plasmodium falciparum. Hydrogenation of the enone to a diarylpropane moiety increased antiplasmodial bioactivity significantly. The influence of the structure of the amine moiety, A-ring substituents, propyl vs ethyl linker, and chloride salt formation on further enhancing antiplasmodial activity was investigated. Several compounds have IC50 values similar to or better than chloroquine (CQ). The most active compound (26) had an IC50 value of 0.01 mu M. No signs of resistance were detected, as can be expected from compounds with structures unrelated to CQ and other currently used antimalarial drugs. Toxicity tests (in vitro CHO cell assay) gave high SI indices.

  DOI：

  10.1021/acs.jnatprod.5b00114
• 作为产物：
  描述：

  2-乙酰基噻吩 、 间羟基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以77%的产率得到(E)-3-(3-hydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  新型双（4,5-二氢吡唑）衍生物的合成，抗菌研究和对接模拟

  摘要：

  通过在碱性介质中比沙可康烯与苯肼的环化反应合成了一系列新的双（3-噻吩基-4,5-二氢吡唑）。与合适的1，ω-dibromoalkanes在无水K的存在查耳酮的O-烷基化反应2 CO 3，无水丙酮和Bu 4 Ñ +我-作为PTC导致以良好的收率bischalcones的形成。所需的查尔酮是从2-乙酰基噻吩与3-羟基苯甲醛的Claisen-Schmidt缩合反应获得的。从其IR，1 H-NMR，13阐明了所制备化合物的结构C‐NMR和ESI‐MS光谱数据。使用串行管稀释法筛选了新合成的化合物对革兰氏阳性，革兰氏阴性细菌菌株和真菌菌株的抗菌效力。还进行了对接模拟，以可视化合成支架2（a – g）和3（a – g）在大肠杆菌活性位点的可能相互作用。

  DOI：

  10.1002/jhet.2835

文献信息

• Synthesis, Antimicrobial Studies, and Docking Simulations of New Bis(4,5-dihydropyrazole) Derivatives
  作者：Mohamad Yusuf、Amanpreet Kaur、Mohammad Abid

  DOI：10.1002/jhet.2835

  日期：2017.7

  were elucidated from their IR, 1H‐NMR, 13C‐NMR, and ESI‐MS spectral data. Newly synthesized compounds were screened for their antimicrobial potencies against Gram‐positive, Gram‐negative bacterial strains, and fungal strains using serial tube dilution method. Docking simulations have also been carried out to visualize the possible interaction of synthesized scaffold 2(a–g) and 3(a–g) at the active sites

  通过在碱性介质中比沙可康烯与苯肼的环化反应合成了一系列新的双（3-噻吩基-4,5-二氢吡唑）。与合适的1，ω-dibromoalkanes在无水K的存在查耳酮的O-烷基化反应2 CO 3，无水丙酮和Bu 4 Ñ +我-作为PTC导致以良好的收率bischalcones的形成。所需的查尔酮是从2-乙酰基噻吩与3-羟基苯甲醛的Claisen-Schmidt缩合反应获得的。从其IR，1 H-NMR，13阐明了所制备化合物的结构C‐NMR和ESI‐MS光谱数据。使用串行管稀释法筛选了新合成的化合物对革兰氏阳性，革兰氏阴性细菌菌株和真菌菌株的抗菌效力。还进行了对接模拟，以可视化合成支架2（a – g）和3（a – g）在大肠杆菌活性位点的可能相互作用。
• Heterocyclic chalcone compounds
  申请人：LASDON FOUNDATION INC

  公开号：US02754299A1

  公开（公告）日：1956-07-10
• Syntheses and in Vitro Antiplasmodial Activity of Aminoalkylated Chalcones and Analogues
  作者：Anke Wilhelm、Pravin Kendrekar、Anwar E. M. Noreljaleel、Efrem T. Abay、Susan L. Bonnet、Lubbe Wiesner、Carmen de Kock、Kenneth J. Swart、Jan Hendrik van der Westhuizen

  DOI：10.1021/acs.jnatprod.5b00114

  日期：2015.8.28

  A series of readily synthesized and inexpensive aminoalkylated chalcones and diarylpropane analogues (1-55) were synthesized and tested against chloroquinone-sensitive (D10 and NF54) and -resistant (Dd2 and K1) strains of Plasmodium falciparum. Hydrogenation of the enone to a diarylpropane moiety increased antiplasmodial bioactivity significantly. The influence of the structure of the amine moiety, A-ring substituents, propyl vs ethyl linker, and chloride salt formation on further enhancing antiplasmodial activity was investigated. Several compounds have IC50 values similar to or better than chloroquine (CQ). The most active compound (26) had an IC50 value of 0.01 mu M. No signs of resistance were detected, as can be expected from compounds with structures unrelated to CQ and other currently used antimalarial drugs. Toxicity tests (in vitro CHO cell assay) gave high SI indices.
• Thiophene and furan appended pyrazoline based fluorescent chemosensors for detection of Al3+ ion
  作者：Manjunath Rangasamy、Kannan Palaninathan

  DOI：10.1016/j.inoche.2019.01.038

  日期：2019.3

  Thiophene and furan appended pyrazoline receptors R1 and R2 were designed and synthesized for selective detection of Al3+ ion. Their photophysical properties were studied by UV-visible and fluorescence spectra. Surprisingly, both receptors R1 and R2 were displayed an excellent selective and sensitive response to Al3+ ion alone over other tested metal ions. Both the receptor R1 and R2 displays 1:1 stoichiometry for [R1-Al3+] and [R2-Al3+] complex and formed with an association constant of 1.84 x 10(4) M-1 and 1.92 x 10(4) M-1 respectively. The limit of detection were calculated for R1 and R2 since 8.92 x 10(-8) M and 1.04 x 10(-7) M by the fluorescence titration method. The thiophene based receptor R1 exhibited superior chemosensor characteristics such as high intensity absorption and emission at longer wavelength as compered that of furan based receptor R2.