tert-butyl (S)-2,5-dihydro-2,5-dioxo-1-<(tert-butoxycarbonyl)methyl>-α-<(tert-butoxycarbonyl)amino>pyrrole-3-propanoate | 144347-44-4

• 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: tert-butyl (S)-2,5-dihydro-2,5-dioxo-1-<(tert-butoxycarbonyl)methyl>-α-<(tert-butoxycarbonyl)amino>pyrrole-3-propanoate
• 英文别名: tert-Butyl(S)-2,5-Dihydro-2,5-dioxo-1-[(tert-butoxycarbonyl)methyl]-α-[(tert-butoxycarbonyl)amino]pyrrole-3-propanoate；tert-butyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[1-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-2,5-dioxopyrrol-3-yl]propanoate
• CAS: 144347-44-4
• 化学式: C₂₂H₃₄N₂O₈
• 分子量: 454.521
• InChiKey: PPZYYRYZDNIKPK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2,5-dihydro-2,5-dioxo-1-<(tert-butoxycarbonyl)methyl>-α-<(tert-butoxycarbonyl)amino>pyrrole-3-propanoate 以0.11 g (68.8%)的产率得到(S)-2,5-Dihydro-2,5-dioxo-α-amino-1-(carboxymethyl)pyrrole-3-propanoic Acid
  参考文献：
  名称：

  Bioactive quisqualic acid analogs

  摘要：

  本发明提供一般公式如下的生物活性化合物：其中R为H，(C.sub.1 -C.sub.4)烷基，(C.sub.3 -C.sub.6)环烷基，(C.sub.3 -C.sub.6)环烷基(C.sub.1 -C.sub.4)烷基，烯丙基，(C.sub.6 -C.sub.10)芳基或(C.sub.1 -C.sub.4)烷基CO.sub.2 Y；Y为H，(C.sub.1 -C.sub.4)烷基或(C.sub.6 -C.sub.10)芳基；每个X分别为H，(C.sub.1 -C.sub.4)烷基，(C.sub.6 -C.sub.10)芳基，(C.sub.3 -C.sub.6)环烷基(C.sub.1 -C.sub.4)烷基，或(C.sub.3 -C.sub.6)环烷烷基；由-表示的键存在或不存在；及其药用盐，以及使用所述化合物刺激哺乳动物神经系统中的受体的方法。

  公开号：

  US05359087A1
• 作为产物：
  描述：

  1-O-tert-butyl 4-O-(2-sulfanylidenepyridin-1-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 为溶剂， 反应 6.75h， 生成 tert-butyl (S)-2,5-dihydro-2,5-dioxo-1-<(tert-butoxycarbonyl)methyl>-α-<(tert-butoxycarbonyl)amino>pyrrole-3-propanoate
  参考文献：
  名称：

  Quisqualic acid analogs: synthesis of .beta.-heterocyclic 2-aminopropanoic acid derivatives and their activity at a novel quisqualate-sensitized site

  摘要：

  Hippocampal CA1 pyramidal cell neurons are sensitized over 30-fold to depolarization by L-2-amino-4-phosphonobutanoic acid (L-AP4) following exposure to L-quisqualic acid. This phenomenon has been termed the QUIS effect. In the present study several novel L-quisqualic acid analogues have been synthesized and tested for their interaction with the different components of the QUIS-effect system. Replacement of the oxadiazolidinedione ring Of L-quisqualic acid with several other types of heterocyclic rings yielded the following quisqualic acid analogues: maleimide 2, N-methylmaleimide 3, N-(carboxymethyl)maleimide 4, succinimides 5A and 5B, and imidazolidinedione 6. None of these analogues were able to mimic the effects Of L-quisqualic acid and sensitize hippocampal CA1 neurons to depolarization by L-AP4. Also, unlike L-serine O-sulfate, L-homocysteinesulfinic acid, or L-alpha-aminoadipic acid, none of the analogues were able to preblock or reverse the QUIS effect. However, when the IC50 values for inhibition of the CA1 synaptic field potential of analogues 2-6 were determined both before and after hippocampal slices were exposed to L-quisqualic acid, the IC50 values of analogues 3 and 4 were found to decrease more than 7-fold. Thus, these two compounds behave like L-AP4 rather than L-quisqualic acid in this system in that they exhibit increased potencies in slices that have been pretreated with L-quisqualic acid even though they cannot themselves induce this sensitization. Compounds 3 and 4, therefore, represent the first non-phosphorus-containing compounds to which hippocampal neurons become sensitized following exposure to L-quisqualic acid. No change in the IC50 values was observed for 5A or 5B. Analogues 2 and 6, on the other hand, displayed a high potency for inhibition of the evoked field potential even prior to treatment of the slices with L-quisqualic acid.

  DOI：

  10.1021/jm00102a014

文献信息

• Bioactive quisqualic acid analogs
  申请人：Regents of the University of Minnesota

  公开号：US05359087A1

  公开（公告）日：1994-10-25

  The present invention provides bioactive compounds of the general formula: ##STR1## wherein R is H, (C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.3 -C.sub.6)cycloalkyl(C.sub.1 -C.sub.4)alkyl, allyl, (C.sub.6 -C.sub.10)aryl or (C.sub.1 -C.sub.4)alkylCO.sub.2 Y; Y is H, (C.sub.1 -C.sub.4)alkyl or (C.sub.6 -C.sub.10)aryl; each X is individually H, (C.sub.1 -C.sub.4)alkyl, (C.sub.6 -C.sub.10)aryl, (C.sub.3 -C.sub.6)cycloalkyl(C.sub.1 -C.sub.4)alkyl, or (C.sub.3 -C.sub.6)cycloatkyl; the bond represented by--is present or is absent; and the pharmaceutically acceptable salts thereof, and methods for using said compounds to stimulate receptors in the mammalian nervous systems.

  本发明提供一般公式如下的生物活性化合物：其中R为H，(C.sub.1 -C.sub.4)烷基，(C.sub.3 -C.sub.6)环烷基，(C.sub.3 -C.sub.6)环烷基(C.sub.1 -C.sub.4)烷基，烯丙基，(C.sub.6 -C.sub.10)芳基或(C.sub.1 -C.sub.4)烷基CO.sub.2 Y；Y为H，(C.sub.1 -C.sub.4)烷基或(C.sub.6 -C.sub.10)芳基；每个X分别为H，(C.sub.1 -C.sub.4)烷基，(C.sub.6 -C.sub.10)芳基，(C.sub.3 -C.sub.6)环烷基(C.sub.1 -C.sub.4)烷基，或(C.sub.3 -C.sub.6)环烷烷基；由-表示的键存在或不存在；及其药用盐，以及使用所述化合物刺激哺乳动物神经系统中的受体的方法。
• US5359087A
  申请人：——

  公开号：US5359087A

  公开（公告）日：1994-10-25
• Quisqualic acid analogs: synthesis of .beta.-heterocyclic 2-aminopropanoic acid derivatives and their activity at a novel quisqualate-sensitized site
  作者：Nalin Subasinghe、Marvin Schulte、Robert J. Roon、James F. Koerner、Rodney L. Johnson

  DOI：10.1021/jm00102a014

  日期：1992.11

  Hippocampal CA1 pyramidal cell neurons are sensitized over 30-fold to depolarization by L-2-amino-4-phosphonobutanoic acid (L-AP4) following exposure to L-quisqualic acid. This phenomenon has been termed the QUIS effect. In the present study several novel L-quisqualic acid analogues have been synthesized and tested for their interaction with the different components of the QUIS-effect system. Replacement of the oxadiazolidinedione ring Of L-quisqualic acid with several other types of heterocyclic rings yielded the following quisqualic acid analogues: maleimide 2, N-methylmaleimide 3, N-(carboxymethyl)maleimide 4, succinimides 5A and 5B, and imidazolidinedione 6. None of these analogues were able to mimic the effects Of L-quisqualic acid and sensitize hippocampal CA1 neurons to depolarization by L-AP4. Also, unlike L-serine O-sulfate, L-homocysteinesulfinic acid, or L-alpha-aminoadipic acid, none of the analogues were able to preblock or reverse the QUIS effect. However, when the IC50 values for inhibition of the CA1 synaptic field potential of analogues 2-6 were determined both before and after hippocampal slices were exposed to L-quisqualic acid, the IC50 values of analogues 3 and 4 were found to decrease more than 7-fold. Thus, these two compounds behave like L-AP4 rather than L-quisqualic acid in this system in that they exhibit increased potencies in slices that have been pretreated with L-quisqualic acid even though they cannot themselves induce this sensitization. Compounds 3 and 4, therefore, represent the first non-phosphorus-containing compounds to which hippocampal neurons become sensitized following exposure to L-quisqualic acid. No change in the IC50 values was observed for 5A or 5B. Analogues 2 and 6, on the other hand, displayed a high potency for inhibition of the evoked field potential even prior to treatment of the slices with L-quisqualic acid.