ethyl 4-(1-methyl-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido) butanoate | 268727-20-4

• 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: ethyl 4-(1-methyl-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido) butanoate
• 英文别名: ethyl γ-[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxamido]butyrate；Ethyl 4-[[1-methyl-4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]pyrrole-2-carbonyl]amino]butanoate
• CAS: 268727-20-4
• 化学式: C₁₈H₂₃N₅O₆
• 分子量: 405.411
• InChiKey: WUFMCVZQUOJDPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-(1-methyl-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido) butanoate 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 Ethyl 4-[[1-methyl-4-[[1-methyl-4-[[1-methyl-4-[(1-methylpyrrole-2-carbonyl)amino]pyrrole-2-carbonyl]amino]pyrrole-2-carbonyl]amino]pyrrole-2-carbonyl]amino]butanoate
  参考文献：
  名称：

  A Convenient Method for the Synthesis of DNA-Recognizing Polyamides in Solution

  摘要：

  A convenient method for the synthesis of polyamides containing N-methylpyrrole (Py) and N-methylimidazole (Im) in solution has been developed. Most of the building blocks have been prepared by a haloform reaction in a simple way that column chromatography can be avoided. By use of the DCC/HOBT coupling reaction, the building blocks prepared have been effectively connected to construct a variety of subchains and polyamides without employing amino protection and deprotection. By use of the present method, an eight-ring polyamide, PyPyPyPy gamma PyImImPy beta Dp (gamma is gamma-aminobutyric acid, beta is beta-alanine, Dp is N,N-dimethylpropyldiamine), has been synthesized by the coupling of two four-ring subchains in one step.

  DOI：

  10.1021/jo000135n
• 作为产物：
  描述：

  1-甲基-4-硝基吡咯-2-羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 ethyl 4-(1-methyl-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido) butanoate
  参考文献：
  名称：

  Synthesis and biophysical studies of hairpin polyamides targeting the Brn-3b and GATA-3 transcriptional sites

  摘要：

  Hairpin polyamide analogs of distamycin A (1) were designed and synthesized to evaluate their ability to bind 5'-ATAGA-3' and 5'-AGATA-3' sequences which are important elements for controlling the function of the Brn-3b and GATA-3 transcriptional factors, respectively. The hairpin polyamides are composed of pyrrole and imidazole units linked together via a.-aminobutyrate (GABA) unit. Hairpins 2b (Py-Py-Im-gamma-Py-Py-Py) and 2c (Im-Py-Py-gamma-Py-Py-Py) were synthesized to target the respective Brn-3b and GATA-3 cognate sequences. Preliminary biophysical studies including thermal denaturation and circular dichroism were performed and the results ascertained the binding of hairpins 2a and 2b to their respective cognate DNA sequences.

  DOI：

  10.1515/hc.2010.002

文献信息

• DNA site-specific N3-adenine methylation targeted to estrogen receptor-positive cells
  作者：Rigel J. Kishton、Sean E. Miller、Heather Perry、Tera Lynch、Mayur Patel、Vinayak K. Gore、Giridhar R. Akkaraju、Sridhar Varadarajan

  DOI：10.1016/j.bmc.2011.07.026

  日期：2011.9

  A compound that can target cells expressing the estrogen receptor (ER), and produce predominantly 3-MeA adducts in those cells has been designed and synthesized. This compound produces mainly the 3-MeA adduct upon reaction with calf thymus DNA, and binds to the ER with a relative binding affinity of 51% (estradiol = 100%). The compound is toxic to ER-expressing MCF-7 breast cancer cells, and pretreatment with the ER antagonist fulvestrant abrogates the toxicity. Pre-treatment of MCF-7 cells with netropsin, which inhibits N3-adenine methylation by the compound, resulted in a threefold decrease in the toxicity. These results demonstrate the feasibility of this strategy for producing 3-MeA adducts in targeted cells. (C) 2011 Elsevier Ltd. All rights reserved.
• A Convenient Method for the Synthesis of DNA-Recognizing Polyamides in Solution
  作者：Junhua Xiao、Gu Yuan、Weiqiang Huang、Albert S. C. Chan、K.-L. Daniel Lee

  DOI：10.1021/jo000135n

  日期：2000.9.1

  A convenient method for the synthesis of polyamides containing N-methylpyrrole (Py) and N-methylimidazole (Im) in solution has been developed. Most of the building blocks have been prepared by a haloform reaction in a simple way that column chromatography can be avoided. By use of the DCC/HOBT coupling reaction, the building blocks prepared have been effectively connected to construct a variety of subchains and polyamides without employing amino protection and deprotection. By use of the present method, an eight-ring polyamide, PyPyPyPy gamma PyImImPy beta Dp (gamma is gamma-aminobutyric acid, beta is beta-alanine, Dp is N,N-dimethylpropyldiamine), has been synthesized by the coupling of two four-ring subchains in one step.
• Synthesis and biophysical studies of hairpin polyamides targeting the Brn-3b and GATA-3 transcriptional sites
  作者：Balaji Babu、Hilary Mackay、Abby Prast、Kristin Dittenhafer、Ryan Davis、Christopher Tronrud、Toni Rice、Sameer Chavda、Moses Lee

  DOI：10.1515/hc.2010.002

  日期：2010.1.1

  Hairpin polyamide analogs of distamycin A (1) were designed and synthesized to evaluate their ability to bind 5'-ATAGA-3' and 5'-AGATA-3' sequences which are important elements for controlling the function of the Brn-3b and GATA-3 transcriptional factors, respectively. The hairpin polyamides are composed of pyrrole and imidazole units linked together via a.-aminobutyrate (GABA) unit. Hairpins 2b (Py-Py-Im-gamma-Py-Py-Py) and 2c (Im-Py-Py-gamma-Py-Py-Py) were synthesized to target the respective Brn-3b and GATA-3 cognate sequences. Preliminary biophysical studies including thermal denaturation and circular dichroism were performed and the results ascertained the binding of hairpins 2a and 2b to their respective cognate DNA sequences.