N-(4-cyanophenyl)-furan-2-yl-carboxamide | 332065-12-0

• 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: N-(4-cyanophenyl)-furan-2-yl-carboxamide
• 英文别名: N-(4-cyanophenyl)furamide；N-(4-cyanophenyl)furan-2-carboxamide
• CAS: 332065-12-0
• 化学式: C₁₂H₈N₂O₂
• mdl: MFCD01815679
• 分子量: 212.208
• InChiKey: MXCQGSKHIBMFMM-UHFFFAOYSA-N

物化性质

• 熔点：
  198.8-199.8 °C
• 沸点：
  289.4±20.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-cyanophenyl)-furan-2-yl-carboxamide 在 盐酸 、 氨 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以14%的产率得到N-(4-amidinophenyl)-furan-2-yl-carboxamide hydrochloride
  参考文献：
  名称：

  Novel pentamidine derivatives: Synthesis, anti-tumor properties and polynucleotide-binding activities

  摘要：

  Novel amidino-substituted conformationally restricted derivatives of pentamidine were synthesized and their antiproliferative activity against several human cancer cell lines determined. It was found that introduction of furandicarboxamide core moiety (9, 10) increases antiproliferative activity as well as selectivity against certain tumor cell lines in comparison with amidino-substituted furan-mono-carboxamide (5, 6). Unlike the furan series where iso-propyl substituted amidine (10) exhibits more potent overall antiproliferative activity and selectivity toward certain cell lines, the same was found for unsubstituted amidines in pyridine series. Amongst all tested compounds the compound 10 is the only one that possesses antiproliferative activity against SW 620 cell line (4 mu M). Spectroscopic studies of the interactions of prepared diamidines with double-stranded DNA and RNA polynucleotides show that all compounds preferentially bind into the minor groove of DNA, while most of them intercalate into RNA. The structure-dependant biological activity and the lack of DNA/RNA selective binding suggest that the mechanism of action of the here-presented compounds is controlled not only by the interactions with cellular nucleic acids, but also with other more specific protein targets. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.001
• 作为产物：
  描述：

  呋喃甲酰氯 、 对氨基苯腈 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以88%的产率得到N-(4-cyanophenyl)-furan-2-yl-carboxamide
  参考文献：
  名称：

  Novel pentamidine derivatives: Synthesis, anti-tumor properties and polynucleotide-binding activities

  摘要：

  Novel amidino-substituted conformationally restricted derivatives of pentamidine were synthesized and their antiproliferative activity against several human cancer cell lines determined. It was found that introduction of furandicarboxamide core moiety (9, 10) increases antiproliferative activity as well as selectivity against certain tumor cell lines in comparison with amidino-substituted furan-mono-carboxamide (5, 6). Unlike the furan series where iso-propyl substituted amidine (10) exhibits more potent overall antiproliferative activity and selectivity toward certain cell lines, the same was found for unsubstituted amidines in pyridine series. Amongst all tested compounds the compound 10 is the only one that possesses antiproliferative activity against SW 620 cell line (4 mu M). Spectroscopic studies of the interactions of prepared diamidines with double-stranded DNA and RNA polynucleotides show that all compounds preferentially bind into the minor groove of DNA, while most of them intercalate into RNA. The structure-dependant biological activity and the lack of DNA/RNA selective binding suggest that the mechanism of action of the here-presented compounds is controlled not only by the interactions with cellular nucleic acids, but also with other more specific protein targets. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.001

文献信息

• Facile Amide Bond Formation from Carboxylic Acids and Isocyanates
  作者：Kaname Sasaki、David Crich

  DOI：10.1021/ol200531k

  日期：2011.5.6

  A wide variety of carboxylic acids in the form of their salts condense with aryl isocyanates at room temperature with loss of carbon dioxide to give the corresponding amides in high yield. Application of the reaction to acyl isocyanates gives unsymmetric imides. The reaction is compatible with hydroxyl groups and both Fmoc and Boc protecting groups for amines and is applicable to aliphatic, aromatic, and heteroaromatic acids.
• Novel pentamidine derivatives: Synthesis, anti-tumor properties and polynucleotide-binding activities
  作者：Ivana Jarak、Marko Marjanović、Ivo Piantanida、Marijeta Kralj、Grace Karminski-Zamola

  DOI：10.1016/j.ejmech.2011.04.001

  日期：2011.7

  Novel amidino-substituted conformationally restricted derivatives of pentamidine were synthesized and their antiproliferative activity against several human cancer cell lines determined. It was found that introduction of furandicarboxamide core moiety (9, 10) increases antiproliferative activity as well as selectivity against certain tumor cell lines in comparison with amidino-substituted furan-mono-carboxamide (5, 6). Unlike the furan series where iso-propyl substituted amidine (10) exhibits more potent overall antiproliferative activity and selectivity toward certain cell lines, the same was found for unsubstituted amidines in pyridine series. Amongst all tested compounds the compound 10 is the only one that possesses antiproliferative activity against SW 620 cell line (4 mu M). Spectroscopic studies of the interactions of prepared diamidines with double-stranded DNA and RNA polynucleotides show that all compounds preferentially bind into the minor groove of DNA, while most of them intercalate into RNA. The structure-dependant biological activity and the lack of DNA/RNA selective binding suggest that the mechanism of action of the here-presented compounds is controlled not only by the interactions with cellular nucleic acids, but also with other more specific protein targets. (C) 2011 Elsevier Masson SAS. All rights reserved.