N-[(1,1-二甲基乙氧基)羰基]-L-丝氨酸 2,5-二氧代-1-吡咯烷基酯 | 39747-65-4

• 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
• 中文名称: N-[(1,1-二甲基乙氧基)羰基]-L-丝氨酸 2,5-二氧代-1-吡咯烷基酯
• 中文别名: N-[(1,1-二甲基乙氧基)羰基]-L-丝氨酸2,5-二氧代-1-吡咯烷基酯；叔丁氧羰基-丝氨酸琥珀酰亚胺酯
• 英文名称: succinimido (tert-butyloxycarbony) serinate
• 英文别名: Boc-Ser-OSu；2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-serinate；(2,5-dioxopyrrolidin-1-yl) (2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 39747-65-4
• 化学式: C₁₂H₁₈N₂O₇
• 分子量: 302.284
• InChiKey: GDEYGBZNQMBETA-ZETCQYMHSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 储存条件：
  -20°C，密封保存，并保持干燥。

反应信息

• 作为反应物：
  描述：

  N-[(1,1-二甲基乙氧基)羰基]-L-丝氨酸 2,5-二氧代-1-吡咯烷基酯 在 吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 N-<(tert-butyloxycarbonyl)-O-acetyl-serinyl>-S-acetylcysteamine
  参考文献：
  名称：

  Synthesis and radioprotective activity of new N-(amino acid)-S-acetylcysteamine and cystamine derivatives

  摘要：

  In order to evaluate the influence of an amino acid conjugation (Sar, Ser, Phe, Pro, Thz) on S-acetylcysteamine, cystamine, N-(amino acid)-S-acetylcysteamine (14-18) and N,N'-bis (amino acid) cystamine (24-28) derivatives have been synthesized and evaluated as potential radioprotectors. Their toxicity and radioprotective activity, as the dose reduction factor (DRF) have been determined (in vivo; ip) and compared with cysteamine and cystamine parent compounds: N-glycyl-S-acetylcysteamine trifluoroacetate 1 and N,N'-bis (glycyl)cystamine bis (trifluoroacetate) 2. Among these compounds, 14 (Sar), 15 (Ser), 15a [Ser (Ac)], 16 [Phe], 24 (Sar) had significant radioprotective activity.

  DOI：

  10.1016/0223-5234(92)90115-h
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 BOC-L-丝氨酸 在 N,N'-二环己基碳二亚胺 作用下， 生成 N-[(1,1-二甲基乙氧基)羰基]-L-丝氨酸 2,5-二氧代-1-吡咯烷基酯
  参考文献：
  名称：

  氯霉素氨基酸类似物对细菌核糖体的结合和作用

  摘要：

  抗生素氯霉素（CHL）以中等亲和力结合在细菌核糖体的肽基转移酶中心，并抑制肽键的形成。作为修饰和潜在改善该抑制剂性质的方法，我们探索了核糖体结合和许多CHL氨基酸类似物的抑制活性。L-组氨酸类似物以超过CHL十倍的亲和力与核糖体结合。一些新合成的类似物能够抑制蛋白质合成，并表现出不同于CHL的作用方式。然而，半合成CHL类似物的抑制特性与其亲和力不相关，并且一般而言，与原始抗生素相比，CHL的氨基酸类似物是不太有效的翻译抑制剂。与三个半合成类似物复合的嗜热栖热菌70S核糖体显示，CHL衍生物在肽基转移酶中心结合，在那里被测化合物的氨酰基部分与rRNA建立了特异相互作用。尽管仍然是效率低下的翻译抑制剂，但合成的化合物仍代表着有前途的化学支架，其靶向核糖体的肽基转移酶中心，并可能适合进一步研究。

  DOI：

  10.1016/j.jmb.2018.01.016

文献信息

• Aminoacyl prodrug derivatives and medicaments for treatment of thromboembolic disorders
  申请人：Lerchen Hans-Georg

  公开号：US20100292230A1

  公开（公告）日：2010-11-18

  The present application relates to prodrug derivatives of 5-chloro-N-((5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide, processes for their preparation, their use for the treatment and/or prophylaxis of diseases, and their use for the manufacture of medicaments for the treatment and/or prophylaxis of diseases, especially of thromboembolic disorders.

  本申请涉及5-氯-N-((5S)-2-氧代-3-[4-(3-氧代吗啡啉-4-基)苯基]-1,3-噁唑烷-5-基}甲基)噻吩-2-羧酰胺的前药衍生物，其制备方法，它们用于治疗和/或预防疾病，以及它们用于制造用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防血栓栓塞性疾病。
• Vinyl ester-based cyclic peptide proteasome inhibitors
  作者：Anna Baldisserotto、Mauro Marastoni、Stella Fiorini、Loretta Pretto、Valeria Ferretti、Riccardo Gavioli、Roberto Tomatis

  DOI：10.1016/j.bmcl.2008.02.016

  日期：2008.3

  The 20S proteasome is a multicatalytic protease complex responsible for the degradation of many proteins in mammalian cells. Specific inhibition of proteasome enzymatic subunits represents a topic of great interest for the development of new drug therapies. Following our previous development of a new class of peptide-based inhibitors bearing a C-terminal vinyl ester residue as a pharmacophoric unit

  20S蛋白酶体是一种多催化蛋白酶复合物，负责哺乳动物细胞中许多蛋白质的降解。蛋白酶体酶亚基的特异性抑制代表了对开发新药物疗法的极大兴趣。继我们先前开发的带有C端乙烯基酯残基的新型基于肽的抑制剂后，它们作为药效团单元能够与苏氨酸催化相互作用，我们在此报告了一系列新的乙烯基酯的合成和生物学性质环肽类似物。这些衍生物中的一些已显示在纳摩尔浓度下抑制蛋白酶体的胰凝乳蛋白酶样活性，并且发现它们的效力取决于四肽环状部分的大小。
• ABUSE RESISTANT LYSINE AMPHETAMINE COMPOUNDS
  申请人：Mickle Travis

  公开号：US20100105781A1

  公开（公告）日：2010-04-29

  The present invention describes compounds, compositions and methods of using the same comprising lysine covalently attached to amphetamine. These compounds and compositions are useful for reducing or preventing abuse and overdose of amphetamine. These compounds and compositions find particular use in providing an abuse-resistant alternative treatment for certain disorders, such as attention deficit hyperactivity disorder (ADHD), ADD, narcolepsy, and obesity. Oral bioavailability of amphetamine is maintained at therapeutically useful doses. At higher doses bioavailability is substantially reduced, thereby providing a method of reducing oral abuse liability. Further, compounds and compositions of the invention decrease the bioavailability of amphetamine by parenteral routes, such as intravenous or intranasal administration, further limiting their abuse liability.

  本发明描述了化合物、组合物及其使用方法，其中赖氨酸共价连接到苯丙胺。这些化合物和组合物有助于减少或预防苯丙胺的滥用和过量使用。这些化合物和组合物在提供某些疾病的耐受性治疗方面特别有用，如注意力缺陷多动障碍（ADHD）、ADD、嗜睡病和肥胖症。在治疗剂量下，苯丙胺的口服生物利用度得以维持。在更高剂量下，生物利用度显著降低，从而提供了一种减少口服滥用风险的方法。此外，本发明的化合物和组合物通过肌肉注射或鼻腔给药等非口服途径降低苯丙胺的生物利用度，进一步限制了它们的滥用风险。
• ABUSE-RESISTANT AMPHETAMINE PRODRUGS
  申请人：Mickle Travis

  公开号：US20090124831A1

  公开（公告）日：2009-05-14

  The invention describes compounds, compositions, and methods of using the same comprising a chemical moiety covalently attached to amphetamine. These compounds and compositions are useful for reducing or preventing abuse and overdose of amphetamine. These compounds and compositions find particular use in providing an abuse-resistant alternative treatment for certain disorders, such as attention deficit hyperactivity disorder (ADHD), ADD, narcolepsy, and obesity. Oral bioavailability of amphetamine is maintained at therapeutically useful doses. At higher doses bioavailability is substantially reduced, thereby providing a method of reducing oral abuse liability. Further, compounds and compositions of the invention decrease the bioavailability of amphetamine by parenteral routes, such as intravenous or intranasal administration, further limiting their abuse liability.

  本发明描述了一种将化学基团共价连接到安非他命的化合物、组合物和使用方法。这些化合物和组合物可用于减少或预防安非他命的滥用和过量。这些化合物和组合物特别适用于提供一种抗滥用替代治疗某些疾病，如注意力缺陷多动障碍（ADHD）、ADD、嗜睡症和肥胖症。在治疗剂量下，口服生物利用度保持在治疗上有用的水平。在较高剂量下，生物利用度显著降低，从而提供了一种降低口服滥用风险的方法。此外，本发明的化合物和组合物通过静脉或鼻腔给药等肌肉注射途径降低了安非他命的生物利用度，进一步限制了它们的滥用风险。
• New cyclic peptide proteasome inhibitors
  作者：Anna Baldisserotto、Mauro Marastoni、Riccardo Gavioli、Roberto Tomatis

  DOI：10.1016/j.bmcl.2009.02.046

  日期：2009.4

  Here we report the study of a new series of vinyl ester cyclopeptide analogues synthesized on the basis of our previous development of a class of cyclopeptides derived from our linear prototype inhibitors. In these compounds, the exocyclic pharmacophoric unit Leu-VE was linked to the gamma-carboxyl group of the glutamic acid residue at the C-terminal. The best analogues of the series have been shown to inhibit the caspase-like activity of the proteasome at nanomolar concentrations and have also demonstrated good resistance to proteolysis and a capacity to permeate the cell membrane. (C) 2009 Elsevier Ltd. All rights reserved.