2'-(4-nitrocinnamoyloxy)acetophenone | 335450-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(4-nitrocinnamoyloxy)acetophenone
• 英文别名: 2-Acetylphenyl (2E)-3-(4-nitrophenyl)-2-propenoate；(2-acetylphenyl) (E)-3-(4-nitrophenyl)prop-2-enoate
• CAS: 335450-43-6
• 化学式: C₁₇H₁₃NO₅
• 分子量: 311.294
• InChiKey: AFKGLXYDECDCDO-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  86.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2'-(4-nitrocinnamoyloxy)acetophenone 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 (2Z,4E)-3-hydroxy-1-(2-hydroxyphenyl)-5-(4-nitrophenyl)penta-2,4-dien-1-one
  参考文献：
  名称：

  1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2012.11.006
• 作为产物：
  描述：

  对硝基肉桂酸 、 2'-羟基苯乙酮 在 吡啶 、 三氯氧磷 作用下， 反应 4.0h， 生成 2'-(4-nitrocinnamoyloxy)acetophenone
  参考文献：
  名称：

  1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2012.11.006

文献信息

• Synthesis and structure elucidation of three series of nitro-2-styrylchromones using 1D and 2D NMR spectroscopy
  作者：Ana I. R. N. A. Barros、Artur M. S. Silva

  DOI：10.1002/mrc.2472

  日期：2009.10

  heterocyclic compounds which have shown significant biological activities. New nitro-2-styrylchromones have been synthesised by the Baker-Venkataraman method, and the structure elucidation was accomplished using extensive 1D (1H, 13C) and 2D NMR spectroscopic studies (COSY, HSQC and HMBC experiments).

  尽管2-苯乙烯基色酮本质上是稀缺的，但它们构成一组已显示出显着生物学活性的氧杂环化合物。通过Baker-Venkataraman方法合成了新的硝基-2-苯乙烯基色酮，并使用大量的1D（1H，13C）和2D NMR光谱研究（COSY，HSQC和HMBC实验）完成了结构阐明。