4-[(4-methoxycarbonylamino-furan-2-carbonyl)-amino]-furan-2-carboxylic acid methyl ester | 1170719-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-[(4-methoxycarbonylamino-furan-2-carbonyl)-amino]-furan-2-carboxylic acid methyl ester
• 英文别名: methyl 4-(4-((methoxycarbonyl)amino)furan-2-carboxamido)furan-2-carboxylate
• CAS: 1170719-64-8
• 化学式: C₁₃H₁₂N₂O₇
• 分子量: 308.247
• InChiKey: PKEXOTWILGTHPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  120.01
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-[(4-methoxycarbonylamino-furan-2-carbonyl)-amino]-furan-2-carboxylic acid methyl ester 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 methyl (5-((5-((2-(1H-indol-3-yl)ethyl)carbamoyl)furan-3-yl)carbamoyl)furan-3-yl)carbamate
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of proximicins A, B and C

  摘要：

  A quick and efficient synthesis and the biological evaluation of promising antitumor-antibiotics proximicins A, B and C are reported. The characteristic repetitive unit of these molecules, the methyl 4-Boc-aminofuran-2-carboxylate 15, was prepared in three synthetic steps in good yield using an optimised copper-catalysed amidation method. The proximicins were evaluated for their antitumor activity using cellular methods. Proximicin B induced apoptosis in both Hodgkin's lymphoma and T-cell leukemia cell lines and proximicin C exhibited significantly high cytotoxicity against glioblastoma and breast carcinoma cells. The proximicins were also screened against Escherichia coli, Enterococcus faecalis and several strains of methicillin-and multidrug-resistant Staphylococcus aureus. Proximicin B showed noteworthy activity against antibiotic-resistant Gram-positive cocci. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.043
• 作为产物：
  描述：

  2-糠酸甲酯 在 盐酸 、 aluminum (III) chloride 、 copper(l) iodide 、 N-羟基-7-氮杂苯并三氮唑 、 溴 、 potassium carbonate 、 氯化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 lithium hydroxide 、 N,N'-二甲基乙二胺 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 53.0h， 生成 4-[(4-methoxycarbonylamino-furan-2-carbonyl)-amino]-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of proximicins A, B and C

  摘要：

  A quick and efficient synthesis and the biological evaluation of promising antitumor-antibiotics proximicins A, B and C are reported. The characteristic repetitive unit of these molecules, the methyl 4-Boc-aminofuran-2-carboxylate 15, was prepared in three synthetic steps in good yield using an optimised copper-catalysed amidation method. The proximicins were evaluated for their antitumor activity using cellular methods. Proximicin B induced apoptosis in both Hodgkin's lymphoma and T-cell leukemia cell lines and proximicin C exhibited significantly high cytotoxicity against glioblastoma and breast carcinoma cells. The proximicins were also screened against Escherichia coli, Enterococcus faecalis and several strains of methicillin-and multidrug-resistant Staphylococcus aureus. Proximicin B showed noteworthy activity against antibiotic-resistant Gram-positive cocci. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.043

文献信息

• Total Synthesis of Proximicin A−C and Synthesis of New Furan-Based DNA Binding Agents
  作者：Falko E. Wolter、Kathrin Schneider、Brian P. Davies、Elke R. Socher、Graeme Nicholson、Oliver Seitz、Roderich D. Süssmuth

  DOI：10.1021/ol901003p

  日期：2009.7.2

  The total synthesis of the natural occurring polyamides proximicin A−C (3−5) has been accomplished. A short and efficient synthesis of a thus far unknown 4-amino-2-furan carboxylic acid was developed. Furthermore, this unique heterocyclic γ-amino-acid was used for the synthesis of a new class of AT-selective DNA-binding agents derived from the natural products combining structural features of the proximicins

  天然存在的聚酰胺的总合成proximicin A-C（3 - 5）已经完成。开发了一种短而有效的迄今未知的4-氨基-2-呋喃羧酸的合成方法。此外，这种独特的杂环γ-氨基酸还用于合成由天然产物衍生的新型AT选择性DNA结合剂，这些结合了Proximicin的结构特征与已知的与DNA结合的天然产物netropsin的结构特征（1）和间他霉素（2）。