(2-(甲基氨基)-2-氧代乙基)氨基甲酸苄酯 | 21855-72-1

• 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: (2-(甲基氨基)-2-氧代乙基)氨基甲酸苄酯
• 英文名称: Cbz-glycine-N-methylamide
• 英文别名: N-[benzyloxycarbonyl]-N'-methyl-glycinamide；Cbz-NHCH2C(O)NHMe；Benzyl (2-(methylamino)-2-oxoethyl)carbamate；benzyl N-[2-(methylamino)-2-oxoethyl]carbamate
• CAS: 21855-72-1
• 化学式: C₁₁H₁₄N₂O₃
• mdl: MFCD22383725
• 分子量: 222.244
• InChiKey: PPWVKWHLWPSSSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090
• 储存条件：
  存储条件：2-8°C，密封保存，确保干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Methyl Cbz-Glycinamide
Synonyms: Benzyl N-[(methylcarbamoyl)methyl]carbamate

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: N-Methyl Cbz-Glycinamide
CAS number: 21855-72-1

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H14N2O3
Molecular weight: 222.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (2-(甲基氨基)-2-氧代乙基)氨基甲酸苄酯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以97%的产率得到2-氨基-N-甲基乙酰胺
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.12.007
• 作为产物：
  描述：

  N-苄氧羰基甘氨酸 、 甲胺 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以64%的产率得到(2-(甲基氨基)-2-氧代乙基)氨基甲酸苄酯
  参考文献：
  名称：

  WO2006/103463

  摘要：

  公开号：

文献信息

• <i>N</i>-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesize <i>cis</i>-enamides through vinyl benziodoxolones
  作者：Daisuke Shimbo、Toshifumi Maruyama、Norihiro Tada、Akichika Itoh

  DOI：10.1039/d1ob00055a

  日期：——

  (cis-β-N-RO-amide-VBXs) from O-alkyl hydroxamic acids in the presence of an ethynyl benziodoxolone–acetonitrile complex (EBX–MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature. The reaction tolerated various O-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products

  本文报道了在乙炔基苯并恶唑啉酮-乙腈络合物（EBX-MeCN）存在下，由O-烷基异羟肟酸立体合成顺式-β- N-烷氧基酰胺乙烯基苯并恶唑烷（顺式-β - N -RO-酰胺-VBXs）。反应在温和的条件下进行，所述条件包括水性溶剂，温和的碱和室温。该反应容许各种衍生自羧酸的O-烷基异羟肟酸，例如氨基酸，药物和天然产物。还使用氧化氘作为氘源合成了乙烯基双氘化的顺式-β - N -MeO-酰胺-VBXs。缬氨酸衍生的顺式将-β - N - MeO-酰胺-VBX立体定向衍生为异羟肟酸衍生的顺式-酰胺，而不会失去立体选择性或降低氘/氢比。
• Sulfonyl amide inhibitors of calcium channel function
  申请人：Hangeland J. Jon

  公开号：US20050245535A1

  公开（公告）日：2005-11-03

  Compounds of formula I its stereoisomers, solvates, and salts, thereof, wherein: a, b, c, d, f, n, m and Ra are defined herein are are inhibitors of calcium channel function, and are useful in treating calcium channel-dependent disorders, including hypertension.

  化合物I的立体异构体、溶剂合物和盐类，其中：a、b、c、d、f、n、m和Ra的定义如下，是钙通道功能的抑制剂，并且在治疗依赖于钙通道的疾病，包括高血压方面具有用处。
• Aqueous solutions containing amino acids and peptides. Part 16.—Solute–solute interactions in solutions containing some N-acetyl-N′-methylamino acid amides
  作者：G. Michael Blackburn、Terence H. Lilley、Peter J. Milburn

  DOI：10.1039/f19858102191

  日期：——

  also obtained for the sparingly soluble substance N-acetylglycyl-L-alaninamide. The results obtained have been used to calculate the pairwise free energy and enthalpy coefficients for the homotactic and heterotactic interactions and these are compared with results obtained earlier on some analogous systems containing the primary amino acid amides. A group-additivity approach has been used to rationalise

  研究了在25°C水溶液中某些N-乙酰基-N '甲基氨基酸酰胺之间发生相互作用的能量。对于N-乙酰-N'-甲基甘氨酰胺，N-乙酰-N'-甲基-L-丙氨酰胺和N-乙酰-N '物种，已获得单组分和两组分溶质系统的渗透系数和稀释焓。-甲基-L-亮氨酰胺。还获得了难溶物质N-乙酰基甘氨酰-L的稀释焓数据-丙氨酰胺。获得的结果已用于计算同规和杂规相互作用的成对自由能和焓系数，并将这些与先前在某些包含伯氨基酸酰胺的类似系统上获得的结果进行比较。群体可加性方法已用于合理化所获得的信息。对于大多数研究的系统来说，这可以很好地工作。
• <i>N</i>-(Benzyloxycarbonyl)glycine Esters and Amides as New Anticonvulsants
  作者：Muriel Geurts、Jacques H. Poupaert、Gerhard K. E. Scriba、Didier M. Lambert

  DOI：10.1021/jm970086f

  日期：1998.1.1

  neutral amino acid exhibiting weak anticonvulsant activities in vivo. Recently, studies have demonstrated that N-(benzyloxycarbonyl)glycine (1) antagonized seizures superior to glycine in addition to activity in the maximal electroshock (MES) test, a convulsive model where glycine is inactive. In the present study a series of ester and amide derivatives of 1 as well as esters of N-(3-phenylpropanoyl)glycine

  甘氨酸是一种小的中性氨基酸，在体内表现出弱的抗惊厥活性。最近，研究表明，在最大电击（MES）测试（一种甘氨酸失活的惊厥模型）中，N-（苄氧羰基）甘氨酸（1）对抗癫痫发作的作用优于甘氨酸。在本研究中，已经制备了一系列的1的酯和酰胺衍生物以及N-（3-苯基丙酰基）甘氨酸的酯（5）。在MES测试以及几种化学诱导的癫痫发作模型中对化合物进行了评估。在所研究的衍生物中，N-（苄氧基羰基）甘氨酸苄酰胺（16）是最有效的化合物，在MES试验中表现出与药物苯妥英相当的抗惊厥活性。腹腔注射后30分钟和3小时测定的中位有效剂量（ED50）为4.8和11.6 mg / kg 行政管理。化合物16还可以在不同的化学诱导模型（例如士的宁，3-巯基丙酸和戊四唑测试）中有效抑制强直性癫痫发作。此外，在150 mg / kg的剂量下，在转子试验中，此处研究的化合物未显示急性神经毒性。结论是，N-（苄氧基羰基）甘氨酸酰胺，特别是16种，是有效的抗惊厥药。
• HETERO RING DERIVATIVE
  申请人：Takahashi Fumie

  公开号：US20120165309A1

  公开（公告）日：2012-06-28

  [Object] A novel and excellent method for preventing or treating rejection in the transplantation of various organs, allergy diseases, autoimmune diseases, hematologic tumor, or the like, based on a PI3Kδ-selective inhibitory action and/or an IL-2 production inhibitory action, and/or a B cell proliferation inhibitory action (including an activation inhibitory action), is provided [Means for Solution] It was found that a 3-substituted triazine or 3-substituted pyrimidine derivative exhibits a PI3Kδ-selective inhibitory action, and/or an IL-2 production inhibitory action, and/or a B cell proliferation inhibitory action (including an activation inhibitory action), and can be an agent for preventing or treating rejection in the transplantation of various organs, allergy diseases (asthma, atopic dermatitis, etc.), autoimmune diseases (rheumatoid arthritis, psoriasis, ulcerative colitis, Crohn's disease, systemic lupus erythematosus, etc.), hematologic tumor (leukemia etc.), or the like, thereby completing the present invention.

  [目标]提供一种基于PI3Kδ选择性抑制作用和/或IL-2产生抑制作用和/或B细胞增殖抑制作用（包括激活抑制作用）的新颖优良方法，用于预防或治疗各种器官移植、过敏性疾病、自身免疫性疾病、血液肿瘤等的排斥反应。 [解决方案]发现3-取代-1,3,5-三嗪或3-取代嘧啶衍生物表现出PI3Kδ选择性抑制作用和/或IL-2产生抑制作用和/或B细胞增殖抑制作用（包括激活抑制作用），可以作为预防或治疗各种器官移植、过敏性疾病（哮喘、特应性皮炎等）、自身免疫性疾病（类风湿性关节炎、银屑病、溃疡性结肠炎、克罗恩病、系统性红斑狼疮等）、血液肿瘤（白血病等）等排斥反应的药物，从而完成了本发明。