methyl 4-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylate | 1401555-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylate
• 英文别名: methyl 4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-1H-pyrrole-2-carboxylate
• CAS: 1401555-59-6
• 化学式: C₁₂H₁₈N₂O₄
• 分子量: 254.286
• InChiKey: OPSRGUWNGBLNOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 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：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylate 在 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 为溶剂， 以86%的产率得到4-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase

  摘要：

  Two principal neurotransmitters are involved in the regulation of mammalian neuronal activity, namely, gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, and L-glutamic acid, an excitatory neurotransmitter. Low GABA levels in the brain have been implicated in epilepsy and several other neurological diseases. Because of GABA's poor ability to cross the blood-brain barrier (BBB), a successful strategy to raise brain GABA concentrations is the use of a compound that does cross the BBB and inhibits or inactivates GABA aminotransferase (GABA-AT), the enzyme responsible for GABA catabolism. Vigabatrin, a mechanism-based inactivator of GABA-AT, is currently a successful therapeutic for epilepsy, but has harmful side effects, leaving a need for improved GABA-AT inactivators. Here, we report the synthesis and evaluation of a series of heteroaromatic GABA analogues as substrates of GABA-AT, which will be used as the basis for the design of novel enzyme inactivators. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.009
• 作为产物：
  描述：

  甲基 4-醛基-1H-吡咯-2-甲酸酯 在 10% Pd/C 、 盐酸羟胺 、 氢气 、 potassium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 methyl 4-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase

  摘要：

  Two principal neurotransmitters are involved in the regulation of mammalian neuronal activity, namely, gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, and L-glutamic acid, an excitatory neurotransmitter. Low GABA levels in the brain have been implicated in epilepsy and several other neurological diseases. Because of GABA's poor ability to cross the blood-brain barrier (BBB), a successful strategy to raise brain GABA concentrations is the use of a compound that does cross the BBB and inhibits or inactivates GABA aminotransferase (GABA-AT), the enzyme responsible for GABA catabolism. Vigabatrin, a mechanism-based inactivator of GABA-AT, is currently a successful therapeutic for epilepsy, but has harmful side effects, leaving a need for improved GABA-AT inactivators. Here, we report the synthesis and evaluation of a series of heteroaromatic GABA analogues as substrates of GABA-AT, which will be used as the basis for the design of novel enzyme inactivators. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.009

文献信息

• [EN] SEQUENCE SELECTIVE PYRROLE AND IMIDAZOLE POLYAMIDE METALLOCOMPLEXES<br/>[FR] MÉTALLOCOMPLEXES POLYAMIDES DE PYRROLE ET IMIDAZOLE SELECTIFS VIS-A-VIS DE SEQUENCES
  申请人：UNIV WESTERN SYDNEY

  公开号：WO2005033077A1

  公开（公告）日：2005-04-14

  The present invention relates to sequence selective compounds for targeting therapeutic or diagnostic groups to polynucleotides. More particularly, the present invention relates to sequence selective targeting of metallocomplexes, such as metallodrugs and metallodiagnostics, to polynucleotides.

  本发明涉及用于将治疗或诊断组靶向到多核苷酸的序列选择性化合物。更具体地说，本发明涉及将金属配合物（如金属药物和金属诊断试剂）的序列选择性靶向到多核苷酸。
• SEQUENCE SELECTIVE PYRROLE AND IMIDAZOLE POLYAMIDE METALLOCOMPLEXES
  申请人：University of Western Sydney

  公开号：EP1678133A1

  公开（公告）日：2006-07-12
• EP1678133A4
  申请人：——

  公开号：EP1678133A4

  公开（公告）日：2008-06-18
• [EN] STAINING AND SORTING GENOMES AND CHROMOSOMES USING SEQUENCE-SPECIFIC POLYAMIDES<br/>[FR] COLORATION ET TRI DE GENOMES ET DE CHROMOSOMES AU MOYEN DE POLYAMIDES SPECIFIQUES DE SEQUENCES
  申请人：PHARMACIA CORP

  公开号：WO2003020877A2

  公开（公告）日：2003-03-13

  Genomic DNA of reproductive cells, including sperm and other cells important in reproduction, are stained and optionally sorted by targeting oligomeric polyamides capable of fluorescence to target DNA sequences and then sorting the cells, for example, by fluorescence activated cell sorting or other cell separation techniques.
• Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase
  作者：Dustin D. Hawker、Richard B. Silverman

  DOI：10.1016/j.bmc.2012.08.009

  日期：2012.10

  Two principal neurotransmitters are involved in the regulation of mammalian neuronal activity, namely, gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, and L-glutamic acid, an excitatory neurotransmitter. Low GABA levels in the brain have been implicated in epilepsy and several other neurological diseases. Because of GABA's poor ability to cross the blood-brain barrier (BBB), a successful strategy to raise brain GABA concentrations is the use of a compound that does cross the BBB and inhibits or inactivates GABA aminotransferase (GABA-AT), the enzyme responsible for GABA catabolism. Vigabatrin, a mechanism-based inactivator of GABA-AT, is currently a successful therapeutic for epilepsy, but has harmful side effects, leaving a need for improved GABA-AT inactivators. Here, we report the synthesis and evaluation of a series of heteroaromatic GABA analogues as substrates of GABA-AT, which will be used as the basis for the design of novel enzyme inactivators. (C) 2012 Elsevier Ltd. All rights reserved.