(2E,4E)-5-phenyl-1-(pyridin-2-yl)penta-2,4-dien-1-one | 1292290-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,4E)-5-phenyl-1-(pyridin-2-yl)penta-2,4-dien-1-one
• 英文别名: (2E,4E)-5-phenyl-1-pyridin-2-ylpenta-2,4-dien-1-one
• CAS: 1292290-27-7
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: LGOMTVGNAFWQLC-JBZDOKMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-phenyl-1-(pyridin-2-yl)penta-2,4-dien-1-one 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 25.0h， 生成 (E)-3-methyl-4-(5-oxo-1-phenyl-5-( pyridin-2-yl)pent-1-en-3-yl)-1-phenyl-1H-pyrazol-5-yl acetate
  参考文献：
  名称：

  Enantioselective 1,4-Michael addition reaction of pyrazolin-5-one derivatives with 2-enoylpyridines catalyzed by Cinchona derived squaramides

  摘要：

  辛可宁衍生的方酰胺催化的吡唑啉-5-酮与2-烯酰吡啶的Michael加成反应，提供了带有两个杂环基团的手性分子，其对映异构体过量高达96%。

  DOI：

  10.1039/c8ob01588k
• 作为产物：
  描述：

  2-乙酰基吡啶 、 肉桂醛 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以18%的产率得到(2E,4E)-5-phenyl-1-(pyridin-2-yl)penta-2,4-dien-1-one
  参考文献：
  名称：

  N-杂环卡宾催化的均戊酸酯环化反应合成小β-内酯融合的环戊烷的非对映选择性

  摘要：

  据报道，NHC用2-烯丙基吡啶或2-烯丙基吡啶N-氧化物环氧化烯类，导致β-内酯小环戊烷的非对映选择性合成。该反应通过生成均烯酸酯等效中间体和...进行。

  DOI：

  10.1039/c5cc02960k

文献信息

• Highly Enantioselective Conjugate Addition of Malononitrile to 2-Enoylpyridines with Bifunctional Organocatalyst
  作者：Nagaraju Molleti、Nirmal K. Rana、Vinod K. Singh

  DOI：10.1021/ol3015607

  日期：2012.9.7

  An efficient enantioselective conjugate addition of malononitrile to a range of β-substituted 2-enoylpyridines catalyzed by cinchona alkaloid-based bifunctional urea catalysts has been developed. Both enantiomers of the products could be achieved with the same level of enantioselectivity by using pseudoenantiomeric catalysts in up to 97% ee and in excellent yields. One of the enantioenriched products

  已经开发了将丙二腈有效地对映选择性共轭加成到由金鸡纳生物碱基双功能尿素催化剂催化的一系列β-取代的2-烯丙基吡啶上。通过使用假对映异构体催化剂以高达97％ee的产率和优异的收率，可以在相同的对映体选择性水平下获得两种产品的两种对映体。对映体富集的产物之一已被转化为高度官能化的哌啶酮衍生物。
• Preparation of azachalcone derivatives via l-proline/ Et3N-catalyzed aldol condensation and study of their antioxidant potential
  作者：Nur Rohman、Bayu Ardiansah、Antonius Herry Cahyana、Nurhayati

  DOI：10.1016/j.mex.2023.102427

  日期：2023.12
• Synthesis, Characterization, Antioxidant, and Anticancer Activity against Colon Cancer Cells of Some Cinnamaldehyde-Based Chalcone Derivatives
  作者：Mohamed A. El-Atawy、Demiana H. Hanna、Ali H. Bashal、Hoda A. Ahmed、Eida M. Alshammari、Ezzat A. Hamed、Abdullah R. Aljohani、Alaa Z. Omar

  DOI：10.3390/biom14020216

  日期：——

  The purpose of the current investigation was to produce cinammaldehyde-based chalcone derivatives (3a–k) to evaluate their potential effectiveness as antioxidant and inhibitory agents versus human Caco-2 cancer cells. The findings obtained using the DPPH assay showed that compound 3e had the highest effective antioxidant activity with the best IC50 value compared with the other compounds. Moreover, the cytotoxic findings revealed that compound 3e was the best compound for inhibiting Caco-2 development in contrast to all other produced derivatives, with the lowest IC50 concentration (32.19 ± 3.92 µM), and it also had no detrimental effects on healthy human lung cells (wi38 cells). Exposure of Caco-2 cells with this IC50 value of compound 3e resulted in a substantial rise in the number of early and late cells that are apoptotic with a significant comet nucleus when compared with control cells employing the annexin V/PI and comet evaluations, respectively. Furthermore, qRT-PCR and ELISA examinations indicated that compound 3e significantly altered the expression of genes and their relative proteins related to apoptosis in the treated Caco-2 cells, thus significantly inhibiting Caco-2 growth through activating Caspase-3 via an intrinsic apoptotic pathway. As a result, compound 3e could serve as an effective therapy for human colon cancer.