(E)-4-(4-n-butylphenyl)-4-oxo-2-butenoic acid | 41297-11-4

• 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: (E)-4-(4-n-butylphenyl)-4-oxo-2-butenoic acid
• 英文别名: 4-oxo-4-(4-butyl-phenyl)-trans-crotonic acid；4-Oxo-4-(4-butyl-phenyl)-trans-crotonsaeure；(2E)-4-(4-butylphenyl)-4-oxobut-2-enoic acid；(E)-4-(4-butylphenyl)-4-oxobut-2-enoic acid
• CAS: 41297-11-4
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: ZUTBWIHBDNGBDF-MDZDMXLPSA-N

物化性质

• 熔点：
  120 °C(Solvent: Benzene)
• 沸点：
  392.6±42.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(4-n-butylphenyl)-4-oxo-2-butenoic acid 在 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 (2E)-4-(4-butylphenyl)-4-oxo-N-phenyl-2-butenamide
  参考文献：
  名称：

  (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalcone–aroylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization

  摘要：

  Antiproliferative activity of twenty-nine (E)-4-aryl-4-oxo-2-butenoic acid amides against three human tumor cell lines (HeLa, FemX, and K562) is reported. Compounds showed antiproliferative activity in one-digit micromolar to submicromolar concentrations. The most active derivatives toward all the cell lines tested bear alkyl substituents on the aroyl moiety of the molecules. Fourteen compounds showed tubulin assembly inhibition at concentrations <20 mu M. The most potent inhibitor of tubulin assembly was unsubstituted compound 1, with IC50 = 2.9 mu M. Compound 23 had an oral LD50 in vivo of 45 mg/kg in mice. Cell cycle analysis on K562 cells showed that compounds 1, 2 and 23 caused accumulation of cells in the G2/M phase, but inhibition of microtubule polymerization is not the principal mode of action of the compounds. Nevertheless, they may be useful leads for the design of a new class of antitubulin agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.006
• 作为产物：
  描述：

  马来酸酐 、 丁苯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-4-(4-n-butylphenyl)-4-oxo-2-butenoic acid
  参考文献：
  名称：

  (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalcone–aroylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization

  摘要：

  Antiproliferative activity of twenty-nine (E)-4-aryl-4-oxo-2-butenoic acid amides against three human tumor cell lines (HeLa, FemX, and K562) is reported. Compounds showed antiproliferative activity in one-digit micromolar to submicromolar concentrations. The most active derivatives toward all the cell lines tested bear alkyl substituents on the aroyl moiety of the molecules. Fourteen compounds showed tubulin assembly inhibition at concentrations <20 mu M. The most potent inhibitor of tubulin assembly was unsubstituted compound 1, with IC50 = 2.9 mu M. Compound 23 had an oral LD50 in vivo of 45 mg/kg in mice. Cell cycle analysis on K562 cells showed that compounds 1, 2 and 23 caused accumulation of cells in the G2/M phase, but inhibition of microtubule polymerization is not the principal mode of action of the compounds. Nevertheless, they may be useful leads for the design of a new class of antitubulin agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.006

文献信息

• Lactone, 18. Mitt. Synthese lactonverbrückter 1,1-Diarylpropylamine
  作者：Jochen Lehmann、Axel Gossen

  DOI：10.1002/ardp.19883210803

  日期：——

  Die Synthese der 3‐Amino‐5,5‐diaryl‐4,5‐dihydro‐2(3H)‐furanone 6a–h durch Addition von Aminen an die β‐Aroylacrylsäuren 1–4 und anschließende Umsetzung von 5a–h mit Phenyllithium schließt die Lücke in der homologen Reihe lactonverbrückter Diarylalkylamine2–5).

  3-氨基-5,5-二芳基-4,5-二氢-2(3H)-呋喃酮6a-h通过将胺加成到β-芳基丙烯酸1-4和随后的5a-h反应合成与苯基锂总结了内酯桥连二芳基烷基胺的同源系列中的差距2-5）。
• 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic Acids Selectively Suppressed Proliferation of Neoplastic Human HeLa Cells. A SAR/QSAR Study
  作者：Branko J. Drakulić、Zorica D. Juranić、Tatjana P. Stanojković、Ivan O. Juranić

  DOI：10.1021/jm0502889

  日期：2005.8.1

  A series of twenty alkyl-, halo-, and methoxy-aryl-substituted 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids were synthesized. The new compounds, called CSAB, suppressed proliferation of human cervix carcinoma, HeLa cells, in vitro in a concentration range of 0.644 to 29.48 mu M/L. Two compounds exhibit antiproliferative activity in sub-micromolar concentrations (16, 19). Five compounds act in low micromolar concentrations (< 2 mu M/L). The most active compounds exert lower cytotoxicity toward healthy human peripheral blood mononuclear cells (PBMC and PBMC+PHA) (selectivity indexes > 10). A strong structure-activity relationship, using estimated log P values and BCUT descriptors, was observed.
• 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic Acids Suppressed Survival of Neoplastic Human HeLa Cells: A QSAR Study
  作者：Branko J. Drakulić、Zorica D. Juranić、Ivan O. Juranić

  DOI：10.1080/10426500590913294

  日期：2005.3.2
• LEHMANN, JOCHEN;GOSSEN, AXEL, ARCH. PHARM., 321,(1988) N 8, C. 443-445
  作者：LEHMANN, JOCHEN、GOSSEN, AXEL

  DOI：——

  日期：——