N-[(二甲基氨甲酰)甲基]氨基甲酸苄酯 | 167303-60-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物
• 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-[(二甲基氨甲酰)甲基]氨基甲酸苄酯
• 英文名称: N-Benzyloxycarbonylglycine dimethylamide
• 英文别名: Benzyl N-[(dimethylcarbamoyl)methyl]carbamate；benzyl N-[2-(dimethylamino)-2-oxoethyl]carbamate
• CAS: 167303-60-8
• 化学式: C₁₂H₁₆N₂O₃
• mdl: MFCD22421521
• 分子量: 236.271
• InChiKey: ZBXKXNUETNSWGE-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  406.2±38.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N-[(二甲基氨甲酰)甲基]氨基甲酸苄酯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 N,N-二甲基甘氨酰胺
  参考文献：
  名称：

  Pd催化的顺序小β-C（sp3）-H芳基化和小δ-C（sp2）-H键的分子内胺化作用，通过N，O-二配位基团合成喹啉酮

  摘要：

  2-喹啉酮衍生物的药理重要性是众所周知的。在这里，我们开发了一种通过钯催化的顺序小β-C（sp3）-H芳基化和选择性分子内C（sp2）-H / NH合成2-quinlinolinone衍生物的有效方案...

  DOI：

  10.1039/c6cc02865a
• 作为产物：
  描述：

  N-苄氧羰基甘氨酸 、 二甲胺 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.31h， 以75%的产率得到N-[(二甲基氨甲酰)甲基]氨基甲酸苄酯
  参考文献：
  名称：

  Application of Predictive QSAR Models to Database Mining:  Identification and Experimental Validation of Novel Anticonvulsant Compounds

  摘要：

  We have developed a drug discovery strategy that employs variable selection quantitative structure-activity relationship (QSAR) models for chemical database mining. The approach starts with the development of rigorously validated QSAR models obtained with the variable selection k nearest neighbor (kNN) method (or, in principle, with any other robust model-building technique). Model validation. is based on several statistical criteria, including the randomization of the target property (Y-randomization), independent assessment of the training set model's predictive power using external test sets, and the establishment of the model's applicability domain. All successful models are employed in database mining concurrently; in each case, only variables selected as a result of model building (termed descriptor pharmacophore) are used in chemical similarity searches comparing active compounds of the training set (queries) with those in chemical databases. Specific biological activity (characteristic of the training set compounds) of external database entries found to be within a predefined similarity threshold of the training set molecules is predicted on the basis of the validated QSAR models using the applicability domain criteria. Compounds judged to have high predicted activities by all or the majority of all models are considered as consensus hits. We report on the application of this computational strategy for the first time for the discovery of anticonvulsant agents in the Maybridge and National Cancer Institute (NCI) databases containing ca. 250 000 compounds combined. Forty-eight anticonvulsant agents of the functionalized amino acid (FAA) series were used to build kNN variable selection QSAR models. The 10 best models were applied to mining chemical databases, and 22 compounds were selected as consensus hits. Nine compounds were synthesized and tested at the NIH Epilepsy Branch, Rockville, MD using the same biological test that was employed to assess the anticonvulsant activity of the training set compounds; of these nine, four were exact database hits and five were derived from the hits by minor chemical modifications. Seven of these nine compounds were confirmed to be active, indicating an exceptionally high hit rate. The approach described in this report can be used as a general rational drug discovery tool.

  DOI：

  10.1021/jm030584q

文献信息

• Indole derivatives as 5-HT1-like agonists for use in migraine
  申请人：Pfizer Inc.

  公开号：US05607960A1

  公开（公告）日：1997-03-04

  The present invention relates to 3,5-disubstituted indole compounds which are selective agonists which act on 5-hdroxytryptamine receptors useful in the treatment of migraine.

  本发明涉及3,5-二取代吲哚化合物，它们是选择性激动剂，作用于对治疗偏头痛有用的5-羟色胺受体。
• An unexpected transformation of benzyl carbamates into α-azidobenzeneacetamides
  作者：Christoph Strässler、Heinz Heimgartner

  DOI：10.1002/hlca.19970800706

  日期：1997.11.3

  treatment of benzyl carbamates 5 (Z-protected secondary amines) with lithium diisopropylamide (LDA), diphenyl phosphorochloridate (DPPC1), and NaN3 yielded the corresponding ã-azidobenzeneacetamides 6 in 45–50% yield (Schemes 2 and 3). In the case of Z-protected diisopropylamine 5b, the phosphate 7 was isolated as a minor product. A reaction mechanism for this unexpected transformation is proposed in

  用二异丙基氨基锂（LDA），二氯磷酸二苯酯（DPPC1）和NaN 3连续处理氨基甲酸苄酯5（Z保护的仲胺），得到相应的-叠氮基苯乙酰胺6，产率为45-50％（方案2和3）。在Z保护的二异丙胺5b的情况下，磷酸盐7作为次要产物被分离。方案4中提出了这种意外转化的反应机理，关键步骤是苄基阴离子的闭环反应生成环氧乙烷中间体B。在粗略的实验中，证明了叠氮苯乙酰胺6通过使用膦介导的偶联（方案5），可以在二肽形成中用作2-苯基甘氨酸合成子。
• Synthesis, physical–chemical characterisation and biological evaluation of novel 2-amido-3-hydroxypyridin-4(1H)-ones: Iron chelators with the potential for treating Alzheimer’s disease
  作者：Alessandra Gaeta、Francisco Molina-Holgado、Xiao L. Kong、Sarah Salvage、Sarah Fakih、Paul T. Francis、Robert J. Williams、Robert C. Hider

  DOI：10.1016/j.bmc.2010.12.007

  日期：2011.2

  A novel class of 2-amido-3-hydroxypyridin-4-one iron chelators is described. These compounds have been designed to behave as suitable molecular probes which will improve our knowledge of the role of iron in neurodegenerative conditions. Neurodegenerative disorders, such as Alzheimer's disease (AD) and Parkinson disease (PD), can be considered as diverse pathological conditions sharing critical metabolic processes such as protein aggregation and oxidative stress. Interestingly, both these metabolic alterations seem to be associated with the involvement of metal ions, including iron. Iron chelation is therefore a potential therapeutic approach. The physico-chemical (pK(a) pFe(3+) and log P) and biological properties (inhibition of iron-containing enzymes) of these chelators have been investigated in order to obtain a suitable profile for the treatment of neurodegenerative conditions. Studies with neuronal cell cultures confirm that the new iron chelators are neuroprotective against beta-amyloid-induced toxicity. (C) 2010 Elsevier Ltd. All rights reserved.
• Structure–activity relationships of the peptide deformylase inhibitor BB-3497: modification of the P2′ and P3′ side chains
  作者：Stephen J. Davies、Andrew P. Ayscough、R.Paul Beckett、John M. Clements、Sheila Doel、Lisa M. Pratt、Zoë M. Spavold、S.Wayne Thomas、Mark Whittaker

  DOI：10.1016/s0960-894x(03)00533-x

  日期：2003.8

  Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to both the P2' and P3' side chains. Enzyme inhibition and antibacterial activity data revealed that a variety of substituents are tolerated at the P2' and P3' positions of the inhibitor backbone. The data from this study highlights the potential for modification at the P2' and P3' positions to optimise the physicochemical properties. (C) 2003 Elsevier Ltd. All rights reserved.
• INDOLE DERIVATIVES AS 5-HT1-LIKE AGONISTS FOR USE IN MIGRAINE
  申请人：Pfizer Limited

  公开号：EP0695301B1

  公开（公告）日：1996-10-30