(2-acetylphenyl) (E)-3-(4-chlorophenyl)prop-2-enoate | 205308-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-acetylphenyl) (E)-3-(4-chlorophenyl)prop-2-enoate
• CAS: 205308-00-5
• 化学式: C₁₇H₁₃ClO₃
• 分子量: 300.741
• InChiKey: CWSSWZMMOAGAOG-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-acetylphenyl) (E)-3-(4-chlorophenyl)prop-2-enoate 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 rel-2-[(3R,4R)-3-(4-chlorophenyl)-4,5-dihydro-3H-pyrazol-4-yl]-4H-chromen-4-one
  参考文献：
  名称：

  2-苯乙烯基色酮与重氮甲烷的1,3-偶极环加成反应合成4-芳基-3-（2-苯甲酰基）-2-吡唑啉

  摘要：

  首次报道的2-苯乙烯基色酮与重氮甲烷的1，3-偶极环加成反应得到4-芳基-3-（2-苯甲酰基）-2-吡唑啉。然而，还发现3-芳基-4-（2-苯甲酰基）-1-吡唑啉是该反应的次要产物。这两个系列的吡唑啉已得到充分表征。

  DOI：

  10.1002/jhet.5570350140
• 作为产物：
  描述：

  4-氯苯甲醛 在 哌啶 、 三氯氧磷 作用下， 以 吡啶 为溶剂， 生成 (2-acetylphenyl) (E)-3-(4-chlorophenyl)prop-2-enoate
  参考文献：
  名称：

  Discovery of a novel dual functional phenylpyrazole-styryl hybrid that induces apoptotic and autophagic cell death in bladder cancer cells

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115335

文献信息

• 1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors
  作者：Nicoletta Desideri、Rossella Fioravanti、Luca Proietti Monaco、Mariangela Biava、Matilde Yáñez、Francesco Ortuso、Stefano Alcaro

  DOI：10.1016/j.ejmech.2012.11.006

  日期：2013.1

  A series of (2E,4E)-1-(2-hydroxyphenyl)-5-phenylpenta-2,4-dien-1-ones (3a-r) and (2Z,4E)-3-hydroxy-1-(2-hydroxyphenyl)-5-phenylpenta-2,4-dien-1-ones (6a-l) were synthesized and evaluated in vitro as inhibitors of the two human Monoamine oxidase (hMAO) isoforms, MAO-A and MAO-B. Most of the compounds showed a selective MAO-B inhibitory activity in the nanomolar or low micromolar range. (2E,4E)-5-(4-Chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)penta-2,4-dien-1-one (3g) and (2E,4E)-5-(4-chlorophenyl)-1-(2,4-dihydroxyphenyl)penta-2,4-dien-1-one (3h) were the most potent hMAO-B inhibitors exhibiting IC50 of 4.51 nM and 1135 nM, respectively, coupled with high selectivity. Moreover, partial recovery of MAO-B activity was observed after repeated washing in the presence of isatin (reversible inhibitor) and compounds 3g and 3h suggesting a reversible inhibition of the enzyme. Molecular mechanics and quantum chemistry methods were used to elucidate the MAO recognition of the most active inhibitors 3g and 3h. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis of 4-Aryl-3-(2-chromonyl)-2-pyrazolines by the 1,3-dipolar cycloaddition of 2-styrylchromones with diazomethane
  作者：Diana C. G. A. Pinto、Artur M. S. Silva、Lúcia M. P. M. Almeida、José A. S. Cavaleiro、Albert Lévai、Tamás Patonay

  DOI：10.1002/jhet.5570350140

  日期：1998.1

  The first reported 1,3-dipolar cycloaddition of 2-styrylchromones with diazomethane afforded 4-aryl-3-(2-chromonyl)-2-pyrazolines. However, 3-aryl-4-(2-chromonyl)-1-pyrazolines have been also found as minor products of this reaction. These two series of pyrazolines have been fully characterized.

  首次报道的2-苯乙烯基色酮与重氮甲烷的1，3-偶极环加成反应得到4-芳基-3-（2-苯甲酰基）-2-吡唑啉。然而，还发现3-芳基-4-（2-苯甲酰基）-1-吡唑啉是该反应的次要产物。这两个系列的吡唑啉已得到充分表征。
• Discovery of a novel dual functional phenylpyrazole-styryl hybrid that induces apoptotic and autophagic cell death in bladder cancer cells
  作者：Sze Wei Leong、JingJing Wang、Kazuhide Shaun Okuda、Qi Su、Yanmin Zhang、Faridah Abas、Suet Lin Chia、Khatijah Yusoff

  DOI：10.1016/j.ejmech.2023.115335

  日期：2023.6