α-phenylstyrylacryl acid | 40136-21-8

• 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: α-phenylstyrylacryl acid
• 英文别名: 2,5-diphenylpenta-2,4-dienoic acid；α-Phenyl-cinnamylidenessigsaeure；2,5-Diphenyl-penta-2,4-diensaeure；1.4-Diphenyl-butadien-(1.3)-carbonsaeure-(1)；α.δ-Diphenyl-α.γ-butadien-α-carbonsaeure；α-Phenyl-β-styryl-acrylsaeure；α-Phenyl-cinnamalessigsaeure；Phenylcinnamenylacrylsaeure；alpha-Phenylcinnamylideneacetic acid
• CAS: 40136-21-8
• 化学式: C₁₇H₁₄O₂
• mdl: MFCD00092578
• 分子量: 250.297
• InChiKey: KBVJPYCDOSNQRI-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C
• 沸点：
  443.8±35.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  α-phenylstyrylacryl acid 在 氯化亚砜 、 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 反应 5.25h， 生成 N-p-chlorophenyl-α-phenylstyrylacrylohydroxamic acid
  参考文献：
  名称：

  α-苯基苯乙烯基丙烯酸异羟肟酸的合成，性质和热力学电离常数

  摘要：

  The synthesis and properties of eight new hydroxamic acids derived from alpha-phenylstyrylacrylic acids are described. These hydroxamic acids, which are crystalline compounds, were characterized by their ultraviolet, infrared, and NMR spectra. The purity was checked by HPLC and HPTLC. The nonaqueous titrations and alkaline hydrolysis are reported. Thermodynamic ionization constants at (25 and 35 +/- 0.1) degrees C are determined. Preliminary studies show that these acids form a chloroform-extractable violet complex with vanadium(V) in 6 M hydrochloric acid solutions.

  DOI：

  10.1021/je00018a013
• 作为产物：
  描述：

  sodium phenylacetate 、 肉桂醛 在 乙酸酐 作用下， 生成 α-phenylstyrylacryl acid
  参考文献：
  名称：

  Rebuffat, Gazzetta Chimica Italiana, 1885, vol. 15, p. 107

  摘要：

  DOI：

文献信息

• Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies
  作者：Eleni Pontiki、Dimitra Hadjipavlou-Litina、Konstantinos Litinas、George Geromichalos

  DOI：10.3390/molecules19079655

  日期：——

  Cinnamic acids have been identified as interesting compounds with antioxidant, anti-inflammatory and cytotoxic properties. In the present study, simple cinnamic acids were synthesized by Knoevenagel condensation reactions and evaluated for the above biological activities. Compound 4ii proved to be the most potent LOX inhibitor. Phenyl- substituted acids showed better inhibitory activity against soybean LOX, and it must be noted that compounds 4i and 3i with higher lipophilicity values resulted less active than compounds 2i and 1i. The compounds have shown very good activity in different antioxidant assays. The antitumor properties of these derivatives have been assessed by their 1/IC50 inhibitory values in the proliferation of HT-29, A-549, OAW-42, MDA-MB-231, HeLa and MRC-5 normal cell lines. The compounds presented low antitumor activity considering the IC50 values attained for the cell lines, with the exception of compound 4ii. Molecular docking studies were carried out on cinnamic acid derivative 4ii and were found to be in accordance with our experimental biological results.

  肉桂酸已被鉴定为具有抗氧化、抗炎和细胞毒性特性的有趣化合物。在本研究中，简单的肉桂酸通过Knoevenagel缩合反应合成，并评估了上述生物活性。化合物4ii证明是最强效的LOX抑制剂。苯基取代的酸显示出对大豆LOX更好的抑制活性，必须注意的是，相对于化合物2i和1i，具有更高亲脂性值的化合物4i和3i活性较低。这些化合物在不同的抗氧化测试中显示出非常好的活性。这些衍生物的抗癌特性已通过其在HT-29、A-549、OAW-42、MDA-MB-231、HeLa和MRC-5正常细胞系中的1/IC50抑制值进行评估。考虑到对细胞系的IC50值，除了化合物4ii外，这些化合物显示出较低的抗癌活性。对肉桂酸衍生物4ii进行了分子对接研究，发现其与我们实验生物结果一致。
• Neber; Foehr; Bauer, Justus Liebigs Annalen der Chemie, 1930, vol. 478, p. 197,214
  作者：Neber、Foehr、Bauer

  DOI：——

  日期：——
• Neber; Paeschke, Chemische Berichte, 1926, vol. 59, p. 2147
  作者：Neber、Paeschke

  DOI：——

  日期：——
• Staudinger; Schneider, Chemische Berichte, 1923, vol. 56, p. 706
  作者：Staudinger、Schneider

  DOI：——

  日期：——
• Posner; Rohde, Chemische Berichte, 1910, vol. 43, p. 2675
  作者：Posner、Rohde

  DOI：——

  日期：——