N-叔丁氧羰基-N’-(4-甲氧基-2,3,6-三甲基苯磺酰基)精氨酸 | 102185-38-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 精氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-叔丁氧羰基-N’-(4-甲氧基-2,3,6-三甲基苯磺酰基)精氨酸
• 中文别名: NΑ叔丁氧羰酰基NΩ(4-甲氧基-2,3,6三甲基苯磺酰)精氨酸；N-叔丁氧羰基-N'-(4-甲氧基-2,3,6-三甲基苯磺酰基)精氨酸
• 英文名称: Nα-(t-butyloxycarbonyl)-Nω-(4-methoxy-2,3,6-trimethylbenzenesulphonyl)-L-arginine
• 英文别名: Boc-Arg(Mtr)-OH；boc-L-Arg(Mtr)-OH；(2S)-5-[amino-[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]methylidene]azaniumyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 102185-38-6
• 化学式: C₂₁H₃₄N₄O₇S
• mdl: MFCD00043097
• 分子量: 486.59
• InChiKey: CXZHJRGYWGPJSD-HNNXBMFYSA-N

物化性质

• 密度：
  1.29±0.1 g/cm3(Predicted)
• 溶解度：
  溶于水或1%醋酸

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  178
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2935 90 90
• 储存条件：
  -20°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Boc-arg(mtr)-oh
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Boc-arg(mtr)-oh
Ingredient name:
CAS number: 102185-38-6

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C21H34N4O7S
Molecular weight: 486.6

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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, sulfur 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：

  N-叔丁氧羰基-N’-(4-甲氧基-2,3,6-三甲基苯磺酰基)精氨酸 在 甲醇 、 sodium tetrahydroborate 、 正丁基锂 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 对甲苯磺酸 、 1-羟基苯并三唑一水物 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.75h， 生成 (2S,4R)-1-acetyl-N-((2S)-1-(benzo[d]thiazol-2-yl)-1-hydroxy-5-(3-((4-methoxy-2,3,6-trimethylphenyl)sulfonyl)guanidino)pentan-2-yl)-4-hydroxypyrrolidine-2-carboxamide
  参考文献：
  名称：

  Potent, Small-Molecule Inhibitors of Human Mast Cell Tryptase. Antiasthmatic Action of a Dipeptide-Based Transition-State Analogue Containing a Benzothiazole Ketone

  摘要：

  Inhibitors of human mast cell tryptase (EC 3.4.21.59) have therapeutic potential for treating allergic or inflammatory disorders. We have investigated transition-state mimetics possessing a heterocycle-activated ketone group and identified in particular benzothiazole ketone (2S)-6 (RWJ-56423) as a potent, reversible, low-molecular-weight tryptase inhibitor with a K-i value of 10 nM. A single-crystal X-ray analysis of the sulfate salt of (2S)-6 confirmed the stereochemistry. Analogues 12 and 15-17 are also potent tryptase inhibitors. Although RWJ-56423 potently inhibits trypsin (K-i = 8.1 nM), it is selective vs other serine proteases, such as kallikrein, plasmin, and thrombin. We obtained an X-ray structure of (2S)-6 complexed with bovine trypsin (1.9-Angstrom resolution), which depicts inter alia a hemiketal involving Ser-189, and hydrogen bonds with His-57 and Gln-192. Aerosol administration of 6 (2R,2S; RWJ-58643) to allergic sheep effectively antagonized antigen-induced asthmatic responses, with 70-75% blockade of the early response and complete ablation of the late response and airway hyperresponsiveness.

  DOI：

  10.1021/jm030050p

文献信息

• Microwave-assisted solution phase peptide synthesis in neat water
  作者：Amit Mahindra、Karthik Nooney、Shrikant Uraon、Krishna K. Sharma、Rahul Jain

  DOI：10.1039/c3ra43040e

  日期：——

  An environmentally benign protocol for solution phase peptide synthesis has been developed in neat water using TBTU/HOBt/DIEA as a coupling combination under microwave irradiation. Key features of this procedure are the replacement of commonly used toxic organic solvents like DMF and NMP, the use of lower amounts of reactants, compatibility with both N-α-Boc- and N-α-Fmoc-protected amino acids and all commonly used side-chain protective groups, short reaction time, and racemization-free synthesis in high yield and purity.

  在微波辐射下，使用TBTU/HOBt/DIEA作为耦合组合，在纯水中开发了一种环境友好的溶液相多肽合成方法。该方法的关键特点包括替代常见的毒性有机溶剂如DMF和NMP，使用更少的反应物，与N-α-Boc保护和N-α-Fmoc保护的氨基酸以及所有常用侧链保护基团兼容，反应时间短，且在高效和高纯度下实现无消旋合成。
• [EN] INHIBITORS OF GROWTH FACTOR ACTIVATION ENZYMES<br/>[FR] INHIBITEURS D'ENZYMES D'ACTIVATION DE FACTEUR DE CROISSANCE
  申请人：UNIV WASHINGTON

  公开号：WO2016144654A1

  公开（公告）日：2016-09-15

  The present invention generally relates to compounds that are useful for inhibiting one or more of hepatocyte growth factor activator, matriptase, hepsin, Factor Xa, or thrombin. The present invention also relates to various methods of using the inhibitor compounds including treating a malignancy, a pre-malignant condition, or cancer by administering an effective amount of the inhibitor to a subject in need thereof.

  本发明通常涉及对抑制肝细胞生长因子激活剂、麦曲丝蛋白、赫普星、Xa因子或凝血酶等的化合物有用的化合物。本发明还涉及使用抑制剂化合物的各种方法，包括通过向需要的受试者施用有效量的抑制剂来治疗恶性肿瘤、癌前病变或癌症。
• Compounds and Compositions as Channel Activating Protease Inhibitors
  申请人：Tully C. David

  公开号：US20070276002A1

  公开（公告）日：2007-11-29

  The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating channel activating proteases, and methods for using such compounds to treat, ameliorate or prevent a condition associated with a channel activating protease, including but not limited to prostasin, PRSS22, TMPRSS11 (e.g., TMPRSS11B, TMPRSS11E), TMPRSS2, TMPRSS3, TMPRSS4 (MTSP-2), matriptase (MTSP-1), CAP2, CAP3, trypsin, cathepsin A, or neutrophil elastase.

  该发明提供了化合物及其药物组合物，这些化合物用于调节通道激活蛋白酶，以及使用这些化合物来治疗、改善或预防与通道激活蛋白酶相关的疾病的方法，包括但不限于前列腺素、PRSS22、TMPRSS11（例如，TMPRSS11B，TMPRSS11E）、TMPRSS2、TMPRSS3、TMPRSS4（MTSP-2）、膜联蛋白（MTSP-1）、CAP2、CAP3、胰蛋白酶、组织蛋白酶A或中性粒细胞弹性蛋白酶。
• Unveiling RNA‐Binding Properties of Verapamil and Preparation of New Derivatives as Inhibitors of HIV‐1 Tat‐TAR Interaction
  作者：Céline Martin、Serena De Piccoli、Marc Gaysinski、Cécile Becquart、Stéphane Azoulay、Audrey Di Giorgio、Maria Duca

  DOI：10.1002/cplu.201900650

  日期：2020.1

  therapeutic applications since coding and non‐coding RNAs bear a pivotal role both in viral and bacterial infections as well as in human pathologies such as cancer. Here, we focused on the targeting of HIV‐1 TAR RNA as a promising target for the development of new anti‐HIV therapies but also as an ideal model to validate the discovery of original RNA ligands. First, we performed an initial screening of a

  由于编码和非编码RNA在病毒和细菌感染以及人类病理疾病（例如癌症）中都起着关键作用，因此现在已经确立了使用小分子靶向RNA的许多治疗应用前景非常广阔的策略。在这里，我们专注于将HIV-1 TAR RNA作为开发新的抗HIV疗法的有希望的目标，同时也是验证原始RNA配体发现的理想模型。首先，我们对抗TAR的化合物库进行了初步筛选，从而发现了市售的钙通道阻滞剂维拉帕米，作为开发新RNA配体的有前途的化学结构。一系列维拉帕米类似物的合成导致了有希望的结构活性关系，并导致了化合物2h的发现，维拉帕米与吲哚片段之间的结合物，作为一种有效且选择性的TAR结合物，能够抑制Tat / TAR相互作用，IC50为18.8 µM。这项工作为发现原始和选择性的RNA配体提供了库筛选的潜力，并说明了如何仍需要研究针对蛋白质靶标的现有药物进行RNA结合，这是小分子靶向RNA领域中的一种有前途的策略。
• Antithrombotic peptides and pseudopeptides
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US05332726A1

  公开（公告）日：1994-07-26

  This invention relates to novel peptide and pseudopeptide derivatives and analogs of aspartic acid which are useful as inhibitors of platelet aggregation and thrombus formation in mammalian blood, to pharmaceutical compositions including such compounds, and to their use in inhibiting thrombus formation and platelet aggregation in mammals.

  这项发明涉及新型肽和伪肽衍生物以及天冬氨酸的类似物，这些物质可用作哺乳动物血液中血小板聚集和血栓形成的抑制剂，还涉及包括这些化合物的药物组合物，以及它们在哺乳动物中抑制血栓形成和血小板聚集中的应用。