N5-苄氧羰基-L-鸟氨酸甲酯盐酸盐 | 5874-75-9

• 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: N5-苄氧羰基-L-鸟氨酸甲酯盐酸盐
• 英文名称: methyl (2S)-2-amino-5-[[(benzyloxy)carbonyl]amino]pentanoate hydrochloride
• 英文别名: H-δ-Z-L-Orn-OMe*HCl；methyl N^δ-(benzyloxycarbonyl)-L-ornithinate hydrochloride；hydrochloride of the methyl ester of N^δ-benzyloxycarbonylornithine；N’-Cbz-L-ornithine methyl ester hydrochloride；H-Orn(Z)-OMe*HCl；Hydrochlorid d. Methylesters v. N^δ-Benzyloxycarbonylornithin；Nδ-benzyloxycarbonyl-L-ornithine methyl ester hydrochloride；N'-Cbz-L-ornithine methyl ester hydrochloride；Orn(Z)-OMe hydrochloride；L-Orn(Z)-OMe.HCl；N⁵-benzyloxycarbonyl-L-ornithine methyl ester; hydrochloride；N⁵-Benzyloxycarbonyl-L-ornithin-methylester; Hydrochlorid；methyl N-5-[(benzyloxy)carbonyl]-L-ornithinate hydrochloride；Nδ-Cbz-L-ornithine-OMe hydrochloride；HCl*H-Nδ-Z-Orn-OMe；H-Orn(Z)-ome hcl；methyl (2S)-2-amino-5-(phenylmethoxycarbonylamino)pentanoate;hydrochloride
• CAS: 5874-75-9
• 化学式: C₁₄H₂₀N₂O₄*ClH
• mdl: MFCD00077027
• 分子量: 316.785
• InChiKey: ZUJMKNWYEVTCNT-YDALLXLXSA-N

物化性质

• 熔点：
  138-141℃
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  90.6
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-Orn(z)-OMe HCl
Synonyms: Methyl N’-(Benzyloxycarbonyl)-L-ornithinate Hydrochloride

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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: H-Orn(z)-OMe HCl
CAS number: 5874-75-9

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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: C14H20N2O4.ClH
Molecular weight: 316.8

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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, hydrogen chloride.

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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：

  N5-苄氧羰基-L-鸟氨酸甲酯盐酸盐 在 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 生成 BOC-L-鸟氨酸甲酯
  参考文献：
  名称：

  Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors

  摘要：

  Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 mu M and 8.5 mu M against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with K-i = 11.5 +/- 0.25 mu M by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.033
• 作为产物：
  描述：

  Boc-Orn(Cbz)-OMe 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以100 %的产率得到N5-苄氧羰基-L-鸟氨酸甲酯盐酸盐
  参考文献：
  名称：

  基于蝶呤的小分子抑制剂，能够与蓖麻毒素 A 链活性位点的二级口袋结合。

  摘要：

  蓖麻毒素 A 链 (RTA) 在核糖体特定区域的腺嘌呤碱基脱嘌呤并导致死亡，其活性位点有两个相邻的特异性口袋。基于这一结构信息，人们进行了许多尝试来开发同时阻断两个口袋的小分子 RTA 抑制剂。然而，没有任何尝试成功。在本研究中，我们合成了带有三肽悬挂物的蝶呤-7-甲酰胺，发现其中之一同时与两个口袋相互作用，表现出良好的RTA抑制活性。对含有新型抑制剂的 RTA 晶体进行 X 射线晶体分析表明，Tyr80 的构象变化是抑制剂同时堵塞两个口袋的重要因素。

  DOI：

  10.1371/journal.pone.0277770
• 作为试剂：
  描述：

  氯化亚砜 、 甲醇 、 、 N'-Cbz-L-鸟氨酸 在 ice 、 氩 、 乙醚 、 N5-苄氧羰基-L-鸟氨酸甲酯盐酸盐 作用下， 以 甲基叔丁基醚 为溶剂， 反应 19.0h， 生成 N5-苄氧羰基-L-鸟氨酸甲酯盐酸盐
  参考文献：
  名称：

  Novel inhibitors of bone reabsorption and antagonists of vitronectin receptors

  摘要：

  本发明涉及公式I中的5元环杂环，其中E、F、G、W、Y和Z具有专利要求中给出的含义，以及它们的制备和用作药物的方法。这些新化合物用作vitronectin受体拮抗剂和骨吸收抑制剂。

  公开号：

  US20010021708A1

文献信息

• Heterocyclic Compound
  申请人：HASHIMOTO Kentaro

  公开号：US20110034469A1

  公开（公告）日：2011-02-10

  The present invention provides a compound represented by the formula wherein each symbol is as defined in the specification, or a salt thereof. The compound of the present invention shows a strong IAP antagonistic activity.

  本发明提供了一种由下式表示的化合物 其中，每个符号如说明书中所定义，或其盐。本发明的化合物表现出强烈的IAP拮抗活性。
• <i>t</i>-Amyloxycarbonyl as a New Protecting Group in Peptide Synthesis. I. The Synthesis and Properties of<i>N</i>-<i>t</i>-Amyloxycarbonylamino Acids and Related Compounds
  作者：Shumpei Sakakibara、Masaru Shin、Masahiko Fujino、Yasutsugu Shimonishi、Sumiko Inoue、Noriyoshi Inukai

  DOI：10.1246/bcsj.38.1522

  日期：1965.9

  that the t-amyloxycarbonyl group (AOC group) can be introduced quite readily into amino acid esters by using t-amyl chloroformate as a reagent, and that the AOC group can be cleaved as smoothly as the t-butoxycarbonyl group (BOC group) under acidic conditions. Since this reagent is much easier to prepare than any other reagents used for the introduction of the BOC group, the new procedure is considered

  已经表明，使用氯甲酸叔戊酯作为试剂，叔戊氧羰基（AOC 基团）可以很容易地引入氨基酸酯中，并且 AOC 基团可以像叔丁氧羰基一样顺利地裂解（ BOC 组）在酸性条件下。由于该试剂比用于引入 BOC 基团的任何其他试剂更容易制备，因此新方法被认为在复杂肽的实际合成中非常有用。3-甲基-3-戊氧基羰基氨基酸也按照在AOC-氨基酸情况下所用的相同程序制备。
• Inhibitors or bone reabsorption and antagonists of vitronectin receptors
  申请人：Hoechst Aktiengesellschaft

  公开号：US06218415B1

  公开（公告）日：2001-04-17

  Novel inhibitors of bone reabsorption and antagonists of vitronectin receptors The present invention relates to 5-membered ring heterocycles of the formula I, in which E, F, G, W, Y and Z have the meaning given in the patent claims, to their preparation and to their use as medicaments. The novel compounds are used as vitronectin receptor antagonists and as inhibitors of bone reabsorption.

  新型骨吸收抑制剂和维脱内钙受体拮抗剂本发明涉及公式I的5-成员环杂环化合物，其中E、F、G、W、Y和Z的含义如专利要求中所述，以及它们的制备和用作药物的用途。这些新型化合物被用作维脱内钙受体拮抗剂和骨吸收抑制剂。
• [EN] PREPARATION AND USE OF REACTIVE OXYGEN SPECIES SCAVENGER<br/>[FR] PRÉPARATION ET UTILISATION D'UN PIÉGEUR D'ESPÈCES RÉACTIVES DE L'OXYGÈNE
  申请人：XW LAB INC

  公开号：WO2019041361A1

  公开（公告）日：2019-03-07

  A compound of Formula (I), pharmaceutically acceptable salts thereof, and individual enantiomers or diastereomers thereof are disclosed. Compositions and methods useful for treatment or suppression of diseases, developmental delays and symptoms related to oxidative stress are also disclosed.

  公开了一种式（I）的化合物，其药用盐以及其个别对映体或二对映体。还公开了用于治疗或抑制疾病、发育延迟和与氧化应激有关症状的组合物和方法。
• Synthesis and biological activity of analogues of vanchrobactin, a siderophore from Vibrio anguillarum serotype O2
  作者：Raquel G. Soengas、Marta Larrosa、Miguel Balado、Jaime Rodríguez、Manuel L. Lemos、Carlos Jiménez

  DOI：10.1039/b719713f

  日期：——

  Several analogues of vanchrobactin, a catechol siderophore isolated from the bacterial fish pathogen Vibrio anguillarum serotype O2 strain RV22, have been synthesized. The biological evaluation of these novel compounds showed that most of them are active as siderophores, as determined by growth promotion assays using the producer strain, as well as V. anguillarum serotype O1, Salmonella enterica, and Erwinia

  已经合成了vanchrobactin的几种类似物，vanchorobactin是一种从细菌鱼病原体鳗弧菌血清型O2菌株RV22中分离出的邻苯二酚铁载体。这些新型化合物的生物学评估表明，通过使用生产菌株以及鳗弧菌血清型O1，沙门氏菌和菊花欧文氏菌的生长促进测定法确定，它们中的大多数都具有铁载体的活性。这些化合物还给出了阳性的铬天青S（CAS）测试。基于这些结果，我们能够推断出一些构效关系。此外，我们发现了具有铁载体活性的类似物，该类似物具有适当的功能（氨基），可用作“特洛伊木马策略”中使用的抗生素载体。