1-(1-Benzofuran-2-yl)-3-thiophen-2-ylprop-2-en-1-one | 139956-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 1-(1-Benzofuran-2-yl)-3-thiophen-2-ylprop-2-en-1-one
• CAS: 139956-05-1
• 化学式: C₁₅H₁₀O₂S
• 分子量: 254.309
• InChiKey: AWWKBIMUPROEFI-UHFFFAOYSA-N

物化性质

• 沸点：
  413.6±45.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-Benzofuran-2-yl)-3-thiophen-2-ylprop-2-en-1-one 在 溶剂黄146 、 potassium hydroxide 、 肼 作用下， 以 吡啶 、 乙醇 、 水 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Synthesis and in vitro cytotoxic evaluation of some novel hexahydroquinoline derivatives containing benzofuran moiety

  摘要：

  一系列新的乙基4-(2-(苯并呋喃-2-基)-4-取代-1,4,5,6,7,8-六氢喹啉-1-基)-苯甲酸酯3a–c通过Michael缩合反应合成，以苯并呋喃查尔酮1a–c和环己酮为原料，得到2-(2-苯并呋喃基)-4-取代-5,6,7,8-四氢-4-H-色烯2a–c，然后与乙基4-氨基苯甲酸酯反应。3a–c与不同的胺缩合得到相应的酰胺4a–e。另一方面，化合物3a–c与水合肼处理得到苯甲酰肼衍生物5a–c。化合物5a–c与不同的硫/异氰酸酯反应得到相应的硫代氨基脲和氨基脲衍生物6a–c。同时，化合物5a–c与氰乙酸乙酯和不同的β-二羰基化合物如乙酰丙酮、乙酰乙酸乙酯和二乙基丙二酸二乙酯反应，分别得到吡唑衍生物7a, b; 8a, b; 9a, b; 和10a–c。此外，5a–c与二硫化碳反应合成相应的噁二唑衍生物11a–c，而与不同的芳香醛缩合得到相应的席夫碱12a–d。对一些新合成的化合物进行对人肝细胞癌HepG-2细胞系的细胞毒性评价发现，测试的化合物对HepG-2细胞生长产生有希望的抑制作用，IC50值范围从11.9到19.3 µg/mL。

  DOI：

  10.1007/s11164-015-2122-2
• 作为产物：
  描述：

  水杨醛 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 1-(1-Benzofuran-2-yl)-3-thiophen-2-ylprop-2-en-1-one
  参考文献：
  名称：

  Synthesis, Characterization, and Anticancer Activity of New Benzofuran Substituted Chalcones

  摘要：

  苯并呋喃衍生物在药物化学中备受关注，由于其多样的药理特性，包括抗癌活性，已引起广泛关注。同样，香豆素类天然产物中常见的亚结构——川芎素，具有强大的抗癌性能。设计、合成和表征了一系列新型的川芎素，3-芳基-1-(5-溴-1-苯并呋喃-2-基)-2-丙酮丙酮（3a-f）。通过使用人类乳腺癌（MCF-7）和前列腺癌（PC-3）细胞株，确定了新合成的（3a-f）和先前合成的（3g-j）川芎素化合物的体外抗肿瘤活性。通过3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴化物（MTT）试验确定了所有化合物的抗肿瘤特性。对测试的川芎素化合物进行细胞存活率试验，并在处理24小时后计算了这些化合物的IC50值。我们的结果表明，测试的川芎素化合物对MCF-7和PC-3细胞株显示出抗肿瘤活性（p < 0.05）。

  DOI：

  10.1155/2016/7678486

文献信息

• 3-(Substituted Aryl)-1-benzofuranyl-2-propenones: Antimicrobial Properties of Some Chalcones-Type Compounds and their 2-Pyrazoline Derivatives
  作者：Demet Coskun、Misir Ahmedzade、Sevda Kirbag

  DOI：10.1155/2011/806854

  日期：——

  2-Acetylbenzofuran on condensation with furan-2-carboxaldehyde and pyrrole-2-carboxaldehyde in methanolic KOH solution yielded the corresponding benzofuran chalcones. These two compounds and nine benzofuran chalcones were synthesized before, were further reacted with hydrazine hydrate in ethanol which led to the formation of 2-pyrazoline derivatives. All the synthesized compounds were characterized by elemental analysis, melting point determination, infrared spectroscopy and nuclear magnetic resonance spectroscopy. Nine chalcone-type compounds and eleven 2-pyrazolines were evaluated for their biological activities against the six bacteria and the three yeast and it was seen that thirteen compounds showed activity. Four of them are chalcone-type compounds showed more or less activity.

  在甲醇性氢氧化钾溶液中，2-乙酰基苯并呋喃与呋喃-2-甲醛和吡咯-2-甲醛缩合，生成相应的苯并呋喃香豆素。这两种化合物和之前合成的九种苯并呋喃香豆素进一步与乙醇中的水合肼反应，形成2-吡唑啉衍生物。所有合成的化合物均通过元素分析、熔点测定、红外光谱和核磁共振光谱进行表征。对九种香豆素类化合物和十一种2-吡唑啉进行了对六种细菌和三种酵母的生物活性评估，发现十三种化合物表现出活性，其中四种是香豆素类化合物表现出不同程度的活性。
• Coşkun, Demet; Kirbaʇ, Sevda, Journal of the Chemical Society of Pakistan, 2015, vol. 37, # 4, p. 769 - 775
  作者：Coşkun, Demet、Kirbaʇ, Sevda

  DOI：——

  日期：——
• Synthesis and in vitro cytotoxic evaluation of some novel hexahydroquinoline derivatives containing benzofuran moiety
  作者：Eman M. Mohi El-Deen、Manal M. Anwar、Sherifa M. Hasabelnaby

  DOI：10.1007/s11164-015-2122-2

  日期：2016.3

  A series of new ethyl 4-(2-(benzofuran-2-yl)-4-substituted-1,4,5,6,7,8-hexahydroquinolin-1-yl)-benzoate 3a–c was synthesized by Michael condensation of benzofuran chalcones 1a–c and cyclohexanone to give 2-(2-benzofuranyl)-4-substituted-5,6,7,8-tetrahydro-4-H -chromene 2a–c, followed by reaction of the latter with ethyl 4-aminobenzoate. Condensation of 3a–c with different amines afforded the corresponding amides 4a–e. On the other hand, upon treatment compounds 3a–c with hydrazine hydrate gave the benzohydrazide derivatives 5a–c. The reaction of compounds 5a–c with different thio/isocyanate gave the corresponding thiosemicarbazide and semicarbazide derivatives 6a–c. Meanwhile compounds 5a–c were reacted with ethyl cyanoacetate and different β-dicarbonyl compounds such as acetyl acetone, ethyl acetoacetate, and diethyl malonate to afford pyrazolyl derivatives 7a, b; 8a, b; 9a, b; and 10a–c, respectively. Moreover, 5a–c were reacted with carbon disulfide to synthesize the corresponding oxadiazolyl derivatives 11a–c, while their condensation with different aromatic aldehydes gave the corresponding Schiff bases 12a–d. Cytotoxic evaluation of some of the newly synthesized compounds against human hepatocellular carcinoma cell lines (HepG-2) revealed that the tested compounds produce promising inhibitory effect against the growth of HepG-2 cells with IC50 values ranged from 11.9 to 19.3 µg/mL.

  一系列新的乙基4-(2-(苯并呋喃-2-基)-4-取代-1,4,5,6,7,8-六氢喹啉-1-基)-苯甲酸酯3a–c通过Michael缩合反应合成，以苯并呋喃查尔酮1a–c和环己酮为原料，得到2-(2-苯并呋喃基)-4-取代-5,6,7,8-四氢-4-H-色烯2a–c，然后与乙基4-氨基苯甲酸酯反应。3a–c与不同的胺缩合得到相应的酰胺4a–e。另一方面，化合物3a–c与水合肼处理得到苯甲酰肼衍生物5a–c。化合物5a–c与不同的硫/异氰酸酯反应得到相应的硫代氨基脲和氨基脲衍生物6a–c。同时，化合物5a–c与氰乙酸乙酯和不同的β-二羰基化合物如乙酰丙酮、乙酰乙酸乙酯和二乙基丙二酸二乙酯反应，分别得到吡唑衍生物7a, b; 8a, b; 9a, b; 和10a–c。此外，5a–c与二硫化碳反应合成相应的噁二唑衍生物11a–c，而与不同的芳香醛缩合得到相应的席夫碱12a–d。对一些新合成的化合物进行对人肝细胞癌HepG-2细胞系的细胞毒性评价发现，测试的化合物对HepG-2细胞生长产生有希望的抑制作用，IC50值范围从11.9到19.3 µg/mL。
• Synthesis, Characterization, and Anticancer Activity of New Benzofuran Substituted Chalcones
  作者：Demet Coşkun、Suat Tekin、Süleyman Sandal、Mehmet Fatih Coşkun

  DOI：10.1155/2016/7678486

  日期：——

  Benzofuran derivatives are of great interest in medicinal chemistry and have drawn considerable attention due to their diverse pharmacological profiles including anticancer activity. Similarly, chalcones, which are common substructures of numerous natural products belonging to the flavonoid class, feature strong anticancer properties. A novel series of chalcones, 3-aryl-1-(5-bromo-1-benzofuran-2-yl)-2-propanones propenones (3a–f), were designed, synthesized, and characterized.In vitroantitumor activities of the newly synthesized (3a–f) and previously synthesized (3g–j) chalcone compounds were determined by using human breast (MCF-7) and prostate (PC-3) cancer cell lines. Antitumor properties of all compounds were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Cell viability assay for the tested chalcone compounds was performed and thelog⁡IC50values of the compounds were calculated after 24-hour treatment. Our results indicate that the tested chalcone compounds show antitumor activity against MCF-7 and PC-3 cell lines (p<0.05).

  苯并呋喃衍生物在药物化学中备受关注，由于其多样的药理特性，包括抗癌活性，已引起广泛关注。同样，香豆素类天然产物中常见的亚结构——川芎素，具有强大的抗癌性能。设计、合成和表征了一系列新型的川芎素，3-芳基-1-(5-溴-1-苯并呋喃-2-基)-2-丙酮丙酮（3a-f）。通过使用人类乳腺癌（MCF-7）和前列腺癌（PC-3）细胞株，确定了新合成的（3a-f）和先前合成的（3g-j）川芎素化合物的体外抗肿瘤活性。通过3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴化物（MTT）试验确定了所有化合物的抗肿瘤特性。对测试的川芎素化合物进行细胞存活率试验，并在处理24小时后计算了这些化合物的IC50值。我们的结果表明，测试的川芎素化合物对MCF-7和PC-3细胞株显示出抗肿瘤活性（p < 0.05）。