(5-{5-[5-(2-Amino-ethylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-ylcarbamoyl}-1-methyl-1H-pyrrol-3-yl)-carbamic acid tert-butyl ester | 386704-69-4

• 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: (5-{5-[5-(2-Amino-ethylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-ylcarbamoyl}-1-methyl-1H-pyrrol-3-yl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[5-[[5-[[5-(2-aminoethylcarbamoyl)-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamate
• CAS: 386704-69-4
• 化学式: C₂₅H₃₄N₈O₅
• 分子量: 526.596
• InChiKey: KMFDLJHOAYUGTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5-{5-[5-(2-Amino-ethylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-ylcarbamoyl}-1-methyl-1H-pyrrol-3-yl)-carbamic acid tert-butyl ester 在 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 brostallicin
  参考文献：
  名称：

  Syntheses of brostallicin starting from distamycin A

  摘要：

  Two syntheses of brostallicin, a DNA minor groove binder now undergoing phase II studies, starting from distamycin A are described. One approach is based upon the selective hydrolysis via imide activation of the C-terminus amide. Besides employing traditional solution-phase synthesis, the convenient use of a polymer-supported reagent is also discussed. The other one is based upon the Curtius rearrangement of the C-terminus side chain of a convenient intermediate, easily prepared in two steps by straightforward functional group manipulation of distamycin A. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01733-1
• 作为产物：
  描述：

  tert-butyl 1-methyl-5-[({1-methyl-5-[({1-methyl-5-[(2-oxo-1-imidazolidinyl)carbonyl]-1H-pyrrol-3-yl}amino)carbonyl]-1H-pyrrol-3-yl}amino)carbonyl]-1H-pyrrol-3-ylcarbamate 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以54%的产率得到(5-{5-[5-(2-Amino-ethylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-ylcarbamoyl}-1-methyl-1H-pyrrol-3-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Syntheses of brostallicin starting from distamycin A

  摘要：

  Two syntheses of brostallicin, a DNA minor groove binder now undergoing phase II studies, starting from distamycin A are described. One approach is based upon the selective hydrolysis via imide activation of the C-terminus amide. Besides employing traditional solution-phase synthesis, the convenient use of a polymer-supported reagent is also discussed. The other one is based upon the Curtius rearrangement of the C-terminus side chain of a convenient intermediate, easily prepared in two steps by straightforward functional group manipulation of distamycin A. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01733-1

文献信息

• Syntheses of brostallicin starting from distamycin A
  作者：Italo Beria、Marcella Nesi

  DOI：10.1016/s0040-4039(02)01733-1

  日期：2002.10

  Two syntheses of brostallicin, a DNA minor groove binder now undergoing phase II studies, starting from distamycin A are described. One approach is based upon the selective hydrolysis via imide activation of the C-terminus amide. Besides employing traditional solution-phase synthesis, the convenient use of a polymer-supported reagent is also discussed. The other one is based upon the Curtius rearrangement of the C-terminus side chain of a convenient intermediate, easily prepared in two steps by straightforward functional group manipulation of distamycin A. (C) 2002 Elsevier Science Ltd. All rights reserved.