3-(2-methoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-methoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one
• 英文别名: 3-(2-Methoxyphenyl)-1-thiophen-2-ylprop-2-en-1-one
• 化学式: C₁₄H₁₂O₂S
• 分子量: 244.314
• InChiKey: QRMITMXJSQXKJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-methoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one 在 sodium 、 四氯化锡 作用下， 以 硝基苯 、 苯 为溶剂， 反应 18.0h， 生成 (4R,5R)-ethyl 4-(2-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-carboxylate
  参考文献：
  名称：

  Synthesis of lignan conjugates via cyclopropanation: Antimicrobial and antioxidant studies

  摘要：

  Ethyl 2-(4-methoxyphenyl)-3-(thiophene-2-carbonyl)cyclopropanecarboxylates 2(a-f) and ethyl 4-aryl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-carboxylates 4(a-f) were synthesized by simple procedure. The synthesized new compounds were screened in vitro for their antimicrobial and antioxidant activities. The compounds 2b and 4f showed excellent antibacterial activity; while 2b and 4f showed remarkable antifungal properties. The results of antioxidant activity studies revealed that compounds 4b and 4f manifested profound antioxidant potential. The docking studies were done for the final compounds. The ADME result indicates that all these molecules possess pharmaceutical properties in the range of 95% of drugs. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.06.005
• 作为产物：
  描述：

  2-乙酰基噻吩 、 邻甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3-(2-methoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of lignan conjugates via cyclopropanation: Antimicrobial and antioxidant studies

  摘要：

  Ethyl 2-(4-methoxyphenyl)-3-(thiophene-2-carbonyl)cyclopropanecarboxylates 2(a-f) and ethyl 4-aryl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-carboxylates 4(a-f) were synthesized by simple procedure. The synthesized new compounds were screened in vitro for their antimicrobial and antioxidant activities. The compounds 2b and 4f showed excellent antibacterial activity; while 2b and 4f showed remarkable antifungal properties. The results of antioxidant activity studies revealed that compounds 4b and 4f manifested profound antioxidant potential. The docking studies were done for the final compounds. The ADME result indicates that all these molecules possess pharmaceutical properties in the range of 95% of drugs. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.06.005

文献信息

• 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.