1-(2-Benzofuranyl)-3-(4-chlorophenyl)-2-propen-1-one | 58583-71-4

• 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: 1-(2-Benzofuranyl)-3-(4-chlorophenyl)-2-propen-1-one
• 英文别名: 1-(1-benzofuran-2-yl)-3-(4-chlorophenyl)prop-2-en-1-one
• CAS: 58583-71-4
• 化学式: C₁₇H₁₁ClO₂
• 分子量: 282.726
• InChiKey: VVXDTELQFOBFFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-Benzofuranyl)-3-(4-chlorophenyl)-2-propen-1-one 、 nalidixic acid hydrazide 在 溶剂黄146 作用下， 120.0 ℃ 、1.0 MPa 条件下， 反应 0.23h， 以78%的产率得到3-[(3-benzo[b]furan-2-yl-5-(4-chlorophenyl)-4,5-dihydro-1H-1-pyrazolyl)carbonyl]-1-ethyl-7-methyl-1,4-dihydro[1,8]naphthyridin-4-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2010.05.035
• 作为产物：
  描述：

  2-乙酰基苯并呋喃 、 4-氯苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(2-Benzofuranyl)-3-(4-chlorophenyl)-2-propen-1-one
  参考文献：
  名称：

  新型血管松弛活性苯并呋喃-吡啶杂化物的合理设计，合成和二维QSAR研究

  摘要：

  3-芳基-1-（苯并呋喃-2-基）-2-丙烯-1-酮3a – c与丙二腈在足够量的相应醇中存在的烷氧基钠存在下，以区域选择性方式进行反应，得到2-烷氧基-4-芳基-6-（苯并呋喃-2-基）-3- pyridinecarbonitriles 4 - 37，其也通过处理ylidenemalononitriles获得图6a - q与2- acetylbenzofuran 1在醇钠的足够量的在相应的醇的存在。使用盐酸去甲肾上腺素标准技术预收缩的大鼠离体胸主动脉环，新的化学实体显示出显着的血管舒张特性。化合物11，16，21，24和30与盐酸胺碘酮在本研究中所使用的参考标准比较显示出显着的活性。CODESSA-Pro软件正在使用获得具有统计学意义的QSAR模型，该模型描述了新合成类似物的生物活性（N  = 31，n  = 5，R 2  = 0.846，R 2 cv OO = 0.765，R 2 cv

  DOI：

  10.1016/j.bmcl.2016.03.054

文献信息

• Design, synthesis and biological evaluation of novel pyrazolo-oxothiazolidine derivatives as antiproliferative agents against human lung cancer cell line A549
  作者：S. Yakaiah、P. Sagar Vijay Kumar、P. Baby Rani、K. Durga Prasad、P. Aparna

  DOI：10.1016/j.bmcl.2018.01.027

  日期：2018.2

  one-pot multicomponent reaction of novel pyrazolo-oxothiazolidine derivatives was achieved by condensation of 1-(benzofuran-2-yl)-3-(substituted-arylprop-2-en-1-ones, thiosemicarbazide and dialkyl acetylenedicarboxylates under the optimized reaction conditions. Synthesised compounds were evaluated for their antiproliferative activity against A549 human lung cancer cell line. Among all the tested compounds

  新型的吡唑并恶噻唑烷衍生物的一种有效的多组分反应是通过在1-苯并呋喃-2-基）-3-（取代的芳基丙-2-烯-1-酮，硫代氨基脲和二烷基乙酰二羧酸二酯上缩合而实现的。优化的反应条件。评估合成的化合物对A549人肺癌细胞的抗增殖活性。在所有测试化合物中，4a（IC 50 – 0.930μg/ mL），4e（IC 50 – 1.207μg/ mL），4f（ IC 50 – 0.808μg/ mL，4g（IC 50 – 1.078μg/ mL），4h（IC 50 – 0.967μg/ mL）和4j（IC与标准药物索拉非尼（IC 50 – 3.779μg/ mL）相比，50 – 2.445μg/ mL）表现出令人鼓舞的活性。分子对接研究表明，化合物4f对受体EGFR（PDB ID代码：1 M17）和VEGFR2（PDB ID代码：4AGD，4ASD）的催化位点具有最大的亲和力。这些新颖的吡唑并-氧杂
• An Efficient One Pot Multicomponent Synthesis of Dihydro Pyrazolyl Bisthiazole Derivatives as Potential Anticancer Agents and their Molecular Docking Studies
  作者：Anjaneyulu Varluvothu、Krishnaiah Vaarla、Rajesh Kumar Kesharwani、Panaganti Leelavathi

  DOI：10.14233/ajchem.2022.23984

  日期：——

  A novel series of dihydropyrazolyl bisthiazoles were synthesized through simple reaction conditions via one pot multicomponent reaction of 2-bromo-1-(4-methyl-2-phenyl thiazol-5-yl)ethan-1-one, thiosemicarbazide and chalcones in the presence of sodium hydroxide in ethanol under reflux condition. The reaction generates two potential five membered heterocylic pharmacophores i.e. Hantzsch thiazole and dihydropyrazole in one step through simple operation, in shorter reaction time with high yields. The newly synthesized compounds were well characterized by IR, 1H, 13C NMR and mass spectral data. All the newly synthesized compounds were evaluated for their anticancer activity against human cancer cell lines and calculated their binding energy values with respect to 3ert protein. Some of the compounds exhibited excellent activity against MCF-7 cancer cell line and studied molecular interaction of probable target protein, human estrogen receptor alpha protein (3ert.pdb) using docking simulation.

  通过简单的反应条件合成了一系列新型二氢吡唑双噻唑 通过 2-溴-1-(4-甲基-2-苯基噻唑-5-基)乙-1-酮、硫代氨基甲酰肼和查耳酮在氢氧化钠存在下于乙醇中的一锅多组分反应，合成了一系列新型二氢吡唑基双噻唑、 回流条件下，在氢氧化钠存在下于乙醇中通过一锅多组分反应合成 2-溴-1-(4-甲基-2-苯基噻唑-5-基)乙-1-酮、硫代氨基甲酰肼和查耳酮。 该反应生成了两种潜在的五元杂环药性物质，即 Hantzsch 噻唑和二氢吡唑。 和二氢吡唑，反应时间短，产率高。 新合成的化合物通过红外光谱、1H、13C NMR 和质谱数据进行了表征。 数据。评估了所有新合成化合物对人类癌细胞株的抗癌活性，并计算了它们与癌细胞株的结合能。 细胞系的抗癌活性，并计算了它们与 3ert 蛋白的结合能值。其中一些 对 MCF-7 癌细胞系表现出卓越的活性。 利用对接模拟研究了可能的靶蛋白--人类雌激素受体 alpha 蛋白（3ert.pdb）的分子相互作用。
• Synthesis and antimicrobial evaluation of 1-(benzofuran-2-yl)-4-nitro-3-arylbutan-1-ones and 3-(benzofuran-2-yl)-4,5-dihydro-5-aryl-1-[4-(aryl)-1,3-thiazol-2-yl]-1H-pyrazoles
  作者：Bakr F. Abdel-Wahab、Hatem A. Abdel-Aziz、Essam M. Ahmed

  DOI：10.1016/j.ejmech.2008.09.029

  日期：2009.6

  2-Acetylbenzofuran 1 on treatment with substituted aldehydes affords the corresponding chalcones 2a-c. Treatment of the chalcones with nitromethane under Michael addition condition furnished the corresponding Michael adducts 3a-c. Cyclocondensation of the chalcones 2a and 2b with thiosemicarbazide under basic refluxing conditions gave 3-(benzofuran-2-yl)-5-(4-aryl)-4,5-dihydropyrazole-1-carbothioamides 4a,b. The pyrazolines 7a-d were synthesized by treating 4a,b with phenacyl bromides in refluxing ethanol. All the synthesized compounds were screened for their antibacterial and antifungal activities at 100 mu g concentration. Some of our compounds showed excellent antimicrobial activities than control drugs. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Jadhav; Choudhari; Patil, Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5443 - 5446
  作者：Jadhav、Choudhari、Patil、Shinde

  DOI：——

  日期：——
• Synthesis of Pyrazole–Oxothiazolidine Hybrids as Potential Anticancer Agents in [Bmim]OH Ionic Liquid Medium
  作者：M. Reddy Gorla、M. Sarma

  DOI：10.1134/s1070428022040157

  日期：2022.4