1-(3-Carboxy-propyl)-2-hydroxy-3-methoxy-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester | 558450-59-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(3-Carboxy-propyl)-2-hydroxy-3-methoxy-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester
• 英文别名: 4-(2-Hydroxy-3-methoxy-2-methoxycarbonyl-5-oxopyrrol-1-yl)butanoic acid
• CAS: 558450-59-2
• 化学式: C₁₁H₁₅NO₇
• 分子量: 273.243
• InChiKey: OWGUTKKAXQSOPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3-Carboxy-propyl)-2-hydroxy-3-methoxy-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester 、 [5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]azanium;chloride 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以32%的产率得到1-(3-{5-[5-(3-Dimethylamino-propylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-ylcarbamoyl}-propyl)-2-hydroxy-3-methoxy-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Isochrysohermidin−Distamycin Hybrids

  摘要：

  The synthesis of the alkylating subunit of the DNA cross-linking agent, isochrysohermidin (2), and its subsequent incorporation into conjugates with distamycin A (1) are described. The DNA binding properties of these agents were compared to that of distamycin A, using a fluorescence intercalator displacement (FID) assay.

  DOI：

  10.1021/jo034326c
• 作为产物：
  描述：

  dimethyl 3-methoxypyrrole-2,5-dicarboxylic acid 在 lithium hydroxide 、 Rose Bengal resin 、 氧气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 27.0h， 生成 1-(3-Carboxy-propyl)-2-hydroxy-3-methoxy-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Isochrysohermidin−Distamycin Hybrids

  摘要：

  The synthesis of the alkylating subunit of the DNA cross-linking agent, isochrysohermidin (2), and its subsequent incorporation into conjugates with distamycin A (1) are described. The DNA binding properties of these agents were compared to that of distamycin A, using a fluorescence intercalator displacement (FID) assay.

  DOI：

  10.1021/jo034326c

文献信息

• Synthesis of Isochrysohermidin−Distamycin Hybrids
  作者：Bryan K. S. Yeung、Dale L. Boger

  DOI：10.1021/jo034326c

  日期：2003.6.1

  The synthesis of the alkylating subunit of the DNA cross-linking agent, isochrysohermidin (2), and its subsequent incorporation into conjugates with distamycin A (1) are described. The DNA binding properties of these agents were compared to that of distamycin A, using a fluorescence intercalator displacement (FID) assay.