ethyl (3-hydroxypropyl)-4-nitropyrrole-2-carboxylate | 374694-40-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: ethyl (3-hydroxypropyl)-4-nitropyrrole-2-carboxylate
• 英文别名: Ethyl 1-(3-hydroxypropyl)-4-nitro-1H-pyrrole-2-carboxylate；ethyl 1-(3-hydroxypropyl)-4-nitropyrrole-2-carboxylate
• CAS: 374694-40-3
• 化学式: C₁₀H₁₄N₂O₅
• 分子量: 242.232
• InChiKey: XAZODZRAKXZLMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (3-hydroxypropyl)-4-nitropyrrole-2-carboxylate 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 70.0 ℃ 、2.07 MPa 条件下， 反应 7.0h， 生成 (3-hydroxypropyl)-4-[(tert-butoxycarbonyl)amino]pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Inhibition of major groove DNA binding bZIP proteins by positive patch polyamides

  摘要：

  Cell permeable synthetic ligands that bind to predetermined DNA sequences offer a chemical approach to gene regulation, provided inhibition of a broad range of DNA transcription factors can be achieved. DNA minor groove binding polyamides containing aminoalkyl substituents at the N-1 of a single pyrrole residue display inhibitory effects for a bZIP protein which binds exclusively in the DNA major groove. For major groove protein inhibition, specific protein-DNA contacts along the phosphate backbone were targeted with the positively charged dimethylamino substituent on the backbone of a minor groove binding polyamide hairpin. Remarkably, these polyamides bind DNA with enhanced affinity and uncompromised specificity when compared to polyamides with the aminoalkyl moiety at the C-terminus. By adding bZlP transcription factors to the class of protein-DNA complexes that can be disrupted by minor groove binding ligands, these results may increase the functional utility of polyamides as regulators of gene expression., (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00122-5
• 作为产物：
  描述：

  4-硝基吡咯-2-羧酸乙酯 、 3-碘丙醇 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以99%的产率得到ethyl (3-hydroxypropyl)-4-nitropyrrole-2-carboxylate
  参考文献：
  名称：

  Inhibition of major groove DNA binding bZIP proteins by positive patch polyamides

  摘要：

  Cell permeable synthetic ligands that bind to predetermined DNA sequences offer a chemical approach to gene regulation, provided inhibition of a broad range of DNA transcription factors can be achieved. DNA minor groove binding polyamides containing aminoalkyl substituents at the N-1 of a single pyrrole residue display inhibitory effects for a bZIP protein which binds exclusively in the DNA major groove. For major groove protein inhibition, specific protein-DNA contacts along the phosphate backbone were targeted with the positively charged dimethylamino substituent on the backbone of a minor groove binding polyamide hairpin. Remarkably, these polyamides bind DNA with enhanced affinity and uncompromised specificity when compared to polyamides with the aminoalkyl moiety at the C-terminus. By adding bZlP transcription factors to the class of protein-DNA complexes that can be disrupted by minor groove binding ligands, these results may increase the functional utility of polyamides as regulators of gene expression., (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00122-5

文献信息

• ANTIPATHOGENIC BENZAMIDE COMPOUNDS
  申请人：BURLI Roland W.

  公开号：US20080200465A1

  公开（公告）日：2008-08-21

  The present invention is related to methods of treating viral and protozoan infections in mammals using antipathogenic benzamide compounds having the formula wherein at least one of the R 1 groups is F, Cl, CN or CF 3 and R 2 , R 3 , Y, Z, m, and n are as defined herein.
• Inhibition of major groove DNA binding bZIP proteins by positive patch polyamides
  作者：Ryan E Bremer、Nicholas R Wurtz、Jason W Szewczyk、Peter B Dervan

  DOI：10.1016/s0968-0896(01)00122-5

  日期：2001.8

  Cell permeable synthetic ligands that bind to predetermined DNA sequences offer a chemical approach to gene regulation, provided inhibition of a broad range of DNA transcription factors can be achieved. DNA minor groove binding polyamides containing aminoalkyl substituents at the N-1 of a single pyrrole residue display inhibitory effects for a bZIP protein which binds exclusively in the DNA major groove. For major groove protein inhibition, specific protein-DNA contacts along the phosphate backbone were targeted with the positively charged dimethylamino substituent on the backbone of a minor groove binding polyamide hairpin. Remarkably, these polyamides bind DNA with enhanced affinity and uncompromised specificity when compared to polyamides with the aminoalkyl moiety at the C-terminus. By adding bZlP transcription factors to the class of protein-DNA complexes that can be disrupted by minor groove binding ligands, these results may increase the functional utility of polyamides as regulators of gene expression., (C) 2001 Elsevier Science Ltd. All rights reserved.