3-[(2-aminophenyl)sulfanyl]-1-(1-benzofuran-2-yl)-3-[4-(dimethylamino) phenyl]propan-1-one | 30608-75-4

• 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: 3-[(2-aminophenyl)sulfanyl]-1-(1-benzofuran-2-yl)-3-[4-(dimethylamino) phenyl]propan-1-one
• 英文别名: Benzofuran-2-yl-(p-dimethylaminostyryl)keton；1--2-<4-dimethylamino-phenyl>-ethylen；1-benzofuran-2-yl-3-(4-dimethylamino-phenyl)-propenone；1-(1-Benzofuran-2-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one；1-(1-benzofuran-2-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
• CAS: 30608-75-4
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: OFDCMBASBRDMBL-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C(Solv: ethanol (64-17-5))
• 沸点：
  467.6±45.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(2-aminophenyl)sulfanyl]-1-(1-benzofuran-2-yl)-3-[4-(dimethylamino) phenyl]propan-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以78%的产率得到3-(benzofuran-2-yl)-5-(4-N,N-dimethylaminophenyl)-2-pyrazoline
  参考文献：
  名称：

  3-(Substituted Aryl)-1-benzofuranyl-2-propenones: Antimicrobial Properties of Some Chalcones-Type Compounds and their 2-Pyrazoline Derivatives

  摘要：

  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。

  DOI：

  10.1155/2011/806854
• 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 3-[(2-aminophenyl)sulfanyl]-1-(1-benzofuran-2-yl)-3-[4-(dimethylamino) phenyl]propan-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

• Design, synthesis, and antitubercular evaluation of novel series of 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs
  作者：Kuntal Manna、Yadvendra K. Agrawal

  DOI：10.1016/j.ejmech.2010.05.035

  日期：2010.9

  Twenty-eight newer 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs were synthesized by microwave irradiation method and evaluated for in-vitro and in-vivo antitubercular activity against multidrug-resistant M. tuberculosis stains. Structure activity relationship study was carried out and found NO2 (o) substituted 3-benzo-furan-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin was most potent antitubercular agent against M. tuberculosis, even better than standard drug isoniazid and comparable with rifampin. Other synthesized compounds 7j, 7f, 7a, 7e and 5d, 5f were found moderate to good activity in in-vitro model at lower IC50 values 85 mu M, 154 mu M, 157 mu M, 164 mu M, 170 mu M and 190 mu ML respectively. In in-vivo animal model compound 7j was drastically reduced the bacterial load in lung and spleen tissues at the dose of 25 mg/kg body weight. (C) 2010 Elsevier Masson SAS. All rights reserved.
• 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, 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）。
• 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。