3-{[4-({4-[(4-Amino-1-methyl-1H-imidazole-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carbonyl}-amino)-1-methyl-1H-imidazole-2-carbonyl]-amino}-propionic acid ethyl ester | 548784-02-7

• 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: 3-{[4-({4-[(4-Amino-1-methyl-1H-imidazole-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carbonyl}-amino)-1-methyl-1H-imidazole-2-carbonyl]-amino}-propionic acid ethyl ester
• CAS: 548784-02-7
• 化学式: C₂₀H₂₆N₁₀O₅
• 分子量: 486.49
• InChiKey: DSTRTOBJUMSHKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  193.08
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-{[4-({4-[(4-Amino-1-methyl-1H-imidazole-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carbonyl}-amino)-1-methyl-1H-imidazole-2-carbonyl]-amino}-propionic acid ethyl ester 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-[[1-Methyl-4-[[1-methyl-4-[[1-methyl-4-[4-[[1-methyl-4-[[1-methyl-4-[(1-methylpyrrole-2-carbonyl)amino]pyrrole-2-carbonyl]amino]pyrrole-2-carbonyl]amino]butanoylamino]imidazole-2-carbonyl]amino]imidazole-2-carbonyl]amino]imidazole-2-carbonyl]amino]propanoic acid
  参考文献：
  名称：

  Synthesis and Photoinduced DNA Cleaving Activity of Hairpin Polyamide–Chlorobenzenesulfonyl Conjugate¶

  摘要：

  A hairpin polyamide-chlorobenzenesulfonyl conjugate was synthesized in solution by a haloform reaction and the dicyclohexvlcarbodiimide/1-hydroxybenzotriazole (DCC/HOBT) coupling reaction. Its ability to cleave DNA was investigated with supercoiled DNA (pBluescript SK), and the DNA cleaving efficiency of chlorobenzenesulfonyl group was enhanced by the hairpin polyamide under UV irradiation (365 nm).

  DOI：

  10.1562/0031-8655(2003)078<0175:sapdca>2.0.co;2
• 作为产物：
  描述：

  3-({1-Methyl-4-[(1-methyl-4-nitro-1H-imidazole-2-carbonyl)-amino]-1H-imidazole-2-carbonyl}-amino)-propionic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 3-{[4-({4-[(4-Amino-1-methyl-1H-imidazole-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carbonyl}-amino)-1-methyl-1H-imidazole-2-carbonyl]-amino}-propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Photoinduced DNA Cleaving Activity of Hairpin Polyamide–Chlorobenzenesulfonyl Conjugate¶

  摘要：

  A hairpin polyamide-chlorobenzenesulfonyl conjugate was synthesized in solution by a haloform reaction and the dicyclohexvlcarbodiimide/1-hydroxybenzotriazole (DCC/HOBT) coupling reaction. Its ability to cleave DNA was investigated with supercoiled DNA (pBluescript SK), and the DNA cleaving efficiency of chlorobenzenesulfonyl group was enhanced by the hairpin polyamide under UV irradiation (365 nm).

  DOI：

  10.1562/0031-8655(2003)078<0175:sapdca>2.0.co;2

文献信息

• Analysis of Noncovalent Complexes between Human Telomeric DNA and Polyamides ContainingN-Methylpyrrole andN-Methylimidazole by Using Electrospray Ionization Mass Spectrometry
  作者：Jiang Zhou、Gu Yuan

  DOI：10.1002/chem.200400803

  日期：2005.2.4

  Electrospray ionization mass spectrometry (ESI-MS) was used to investigate noncovalent complexes formed between four novel polyamides containing N-methylpyrrole (Py) and N-methylimidazole (Im), and human telomeric DNA. Of the four polyamides investigated, PyPyPygammaImImImbetaDp (3) had the highest binding affinity towards the duplex d(TTAGGGTTAGGG/CCCTAACCCTAA) (D1). Results of competition analysis

  电喷雾电离质谱（ESI-MS）用于研究包含N-甲基吡咯（Py）和N-甲基咪唑（Im）的四种新型聚酰胺与人类端粒DNA之间形成的非共价复合物。在研究的四种聚酰胺中，PyPyPygammaImImImbetaDp（3）对双链体d（TTAGGGTTAGGG / CCCTAACCCTAA）（D1）的结合亲和力最高。竞争分析结果表明，聚酰胺与D1的结合亲和力依次为PyPyPygammaImImImbetaDp（3）> PyPyPyPygammaPyImImPybetaDp（4）> PyPyPyPybetaImImImbetaDp（2）>> ImImImbetaDp（2）。MS / MS光谱证实，D1和发夹形聚酰胺之间的结合比三环聚酰胺更稳定。相反，在单链d（TTAGGGTTAGGG）（D2）的情况下，结合顺序变为ImImImbetaDp（1）>