methyl E-3-(2-furyl)-2-phenylacrylate | 42307-47-1

• 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: methyl E-3-(2-furyl)-2-phenylacrylate
• 英文别名: (E)-2-phenyl-3-(2'-furyl)-propenoic acid methyl ester；methyl (2E)-3-(furan-2-yl)-2-phenylprop-2-enoate；methyl (E)-3-(furan-2-yl)-2-phenylprop-2-enoate
• CAS: 42307-47-1
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: JJJQIAJTTBHMEW-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl E-3-(2-furyl)-2-phenylacrylate 在 对苯醌 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 methyl E-3-{5-[5-N-(N-morpholinylamidino)benzimidazolyl-2-furyl]}-2-phenylacrylate
  参考文献：
  名称：

  Synthesis and antitumor evaluation of some new substituted amidino-benzimidazolyl-furyl-phenyl-acrylates and naphtho[2,1-b]furan-carboxylates

  摘要：

  The multistep synthesis of a series of substituted amidino-benzimidazolyl-furyl-phenyl-acrylic acid's esters and substituted amidino-benzimidazolyl-naphtho[2,1-b]furan-carboxylic acid's esters is described starting from corresponding 3-(2-furyl)-2-phenyl-acrylic acids. The new compounds were tested on the cytostatic activities against malignant cell lines: pancreatic carcinoma (MiaPaCa2), breast carcinoma (MCF7), cervical carcinoma (HeLa), laryngeal carcinoma (Hep2), colon carcinoma (HT 29), melanoma (HBL), and human fibroblasts cell line (WI38). All compounds inhibited the proliferation of tumor cell lines. Inhibitory effect of examined compounds depended on concentration, but without significant difference among the type of tumor cells. The compounds 2 and 5 exerted very low inhibitory effect on the growth of human fibroblasts. Unsubstituted derivative 8 has not inhibited any tested cell lines.

  DOI：

  10.1016/s0014-827x(03)00197-6
• 作为产物：
  描述：

  甲醇 、 3-(呋喃-2-基)-2-苯基丙-2-烯酸 在 硫酸 作用下， 生成 methyl E-3-(2-furyl)-2-phenylacrylate
  参考文献：
  名称：

  Maxim; Stancovici, Bulletin de la Societe Chimique de France, 1935, vol. <5> 2, p. 600,601

  摘要：

  DOI：

文献信息

• Synthesis, photochemical synthesis, DNA binding and antitumor evaluation of novel cyano- and amidino-substituted derivatives of naphtho-furans, naphtho-thiophenes, thieno-benzofurans, benzo-dithiophenes and their acyclic precursors
  作者：Kristina Starčević、Marijeta Kralj、Ivo Piantanida、Lidija Šuman、Krešimir Pavelić、Grace Karminski-Zamola

  DOI：10.1016/j.ejmech.2006.03.012

  日期：2006.8

  their thiophene analogues, all non-charged derivatives and amidino-phenyl-substituted analogues didn't show acceptable photoconversion. The significantly stronger antiproliferative activity of cyclic analogues could be correlated to the property of these molecules to intercalate into DNA. The acyclic molecules did not show any interaction with DNA, correlating with the inferior biological activity, except

  作为通过光诱导形成嵌入剂改善传统光动力疗法替代方法研究的一部分，我们合成了一系列新型杂环化合物及其无环前体。现在，我们就其光诱导环化的潜力，与DNA的相互作用以及体外对肿瘤细胞生长的抑制作用，报告其合成/表征的详细信息。在研究的化合物中，只有酰胺基-呋喃基取代的丙烯酸苯基酯可以有效地转化为相应的萘呋喃，而它们的噻吩类似物，所有不带电荷的衍生物和酰胺基-苯基取代的类似物均未显示出可接受的光转化。环状类似物明显更强的抗增殖活性可能与这些分子插入DNA中的特性有关。
• Conformations of E-2-phenyl-3(2′-furyl)propenoic acid and its methyl ester in various solvents—an NMR study
  作者：P. Forgó、K. Felföldi、I. Pálinkó

  DOI：10.1016/j.molstruc.2004.11.052

  日期：2005.6

  The conformations of E-2-phenyl-3(2'-furyl)propenoic acid and its methyl ester were investigated by NMR spectroscopy. Applying various solvents (methanol, chloroform and dimethyl sulfoxide) the possible conformers in solutions were studied by two-dimensional NOESY measurements. Irrespective to the solvents and whether the investigated moiety was the ester or the acid dimer, no conformational preferences

  E-2-苯基-3(2'-呋喃基)丙烯酸及其甲酯的构象通过核磁共振光谱进行了研究。应用各种溶剂（甲醇、氯仿和二甲亚砜），通过二维 NOESY 测量研究了溶液中可能的构象异构体。不考虑溶剂以及所研究的部分是酯还是酸二聚体，通过实验无法确定构象偏好。
• Maxim; Stancovici, Bulletin de la Societe Chimique de France, 1935, vol. <5> 2, p. 600,601
  作者：Maxim、Stancovici

  DOI：——

  日期：——
• Synthesis and antitumor evaluation of some new substituted amidino-benzimidazolyl-furyl-phenyl-acrylates and naphtho[2,1-b]furan-carboxylates
  作者：M. Hranjec、M. Grdiša、K. Pavelic、D.W. Boykin、G. Karminski-Zamola

  DOI：10.1016/s0014-827x(03)00197-6

  日期：2003.12

  The multistep synthesis of a series of substituted amidino-benzimidazolyl-furyl-phenyl-acrylic acid's esters and substituted amidino-benzimidazolyl-naphtho[2,1-b]furan-carboxylic acid's esters is described starting from corresponding 3-(2-furyl)-2-phenyl-acrylic acids. The new compounds were tested on the cytostatic activities against malignant cell lines: pancreatic carcinoma (MiaPaCa2), breast carcinoma (MCF7), cervical carcinoma (HeLa), laryngeal carcinoma (Hep2), colon carcinoma (HT 29), melanoma (HBL), and human fibroblasts cell line (WI38). All compounds inhibited the proliferation of tumor cell lines. Inhibitory effect of examined compounds depended on concentration, but without significant difference among the type of tumor cells. The compounds 2 and 5 exerted very low inhibitory effect on the growth of human fibroblasts. Unsubstituted derivative 8 has not inhibited any tested cell lines.