Boc-D-3-氰基苯丙氨酸 | 205445-56-3

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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: Boc-D-3-氰基苯丙氨酸
• 中文别名: 叔丁氧羰基-D-3-氰基苯丙氨酸；N-叔丁氧羰基-D-3-氰基苯丙氨酸
• 英文名称: Boc-D-3-cyanophenylalanine
• 英文别名: Boc-D-Phe(3-CN)-OH；(2R)-3-(3-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 205445-56-3
• 化学式: C₁₅H₁₈N₂O₄
• 分子量: 290.319
• InChiKey: FDQDHMZKOPOWFE-GFCCVEGCSA-N

物化性质

• 沸点：
  485.4±40.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险等级：
  6.1
• WGK Germany：
  3
• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-d-3-cyanophenylalanine
Synonyms:

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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: Boc-d-3-cyanophenylalanine
CAS number: 205445-56-3

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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: C15H18N2O4
Molecular weight: 290.3

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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
UN Number: UN3439 Class: 6.1 Packing group: III
Proper shipping name: NITRILES, TOXIC, SOLID, N.O.S. (Boc-d-3-cyanophenylalanine)

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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：

  Boc-D-3-氰基苯丙氨酸 在 N-甲基吗啉 、 三甲基氯硅烷 、 palladium 10% on activated carbon 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢溴酸 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 11.5h， 生成 methyl (13S,16R)-4,8,15-trioxo-16-((phenylmethyl)sulfonamido)-3,9,14-triaza-1,11(1,3),6(1,4)-tribenzenacycloheptadecaphane-13-carboxylate
  参考文献：
  名称：

  开发高效和选择性纤溶酶抑制剂的新策略

  摘要：

  开发了一种新的基于结构的策略，用于设计有效的和选择性的纤溶酶抑制剂。这些化合物可以通过复分解或铜催化的叠氮化物炔烃环加成结合标准肽偶联作用，在底物类似物抑制剂的P3和P2氨基酸残基之间环化来制备。最有效的双三唑衍生物10抑制纤溶酶和血浆激肽释放酶，其K i分别为0.77和2.4 nM，而它对相关的胰蛋白酶样丝氨酸蛋白酶，凝血酶，Xa因子或活化的蛋白C的活性较弱。那抑制剂10采用紧凑而坚固的结构，非常适合纤溶酶和血浆激肽释放酶的相对开放的活性位点，而其他酶环中存在的空间要求残基却拒绝了它。这些来自建模的结果证实了在酶动力学研究中发现的抑制剂10的选择性分布。此类化合物可能是有用的先导结构，可用于开发新的抗纤维蛋白溶解药物，用于通过心肺分流术或器官移植来减少出血并发症的心脏外科手术。

  DOI：

  10.1021/jm2011996
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 D-3-氰基苯丙氨酸 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 生成 Boc-D-3-氰基苯丙氨酸
  参考文献：
  名称：

  [EN] SERINE PROTEASE INHIBITORS
  [FR] INHIBITEURS DE LA SÉRINE PROTÉASE

  摘要：

  公开号：

  WO2012004678A3

文献信息

• [EN] NOVEL CLOSTRIDIUM DIFFICILE TOXIN INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE TOXINE DE CLOSTRIDIUM DIFFICILE
  申请人：VENENUM BIODESIGN LLC

  公开号：WO2017214359A1

  公开（公告）日：2017-12-14

  The present invention relates to benzodiazepine derivative compounds of formula (I), or pharmaceutically acceptable salts thereof. The present benzodiazepine compounds are useful Clostridium difficile inhibitors in the treatment of Clostridium difficile infection in humans. The present invention provides a pharmaceutical composition containing benzodiazepine compounds of formula (I) and a method of making as well as a method of using the same in treating patients infected with Clostridium difficile infection by administering the same. The compounds of the present invention may be used in combination with additional antibiotics or anti-toxin antibody drugs.

  本发明涉及式(I)的苯二氮卓衍生物化合物，或其药学上可接受的盐。目前的苯二氮卓衍生物在治疗人类的克罗斯特氏梭菌感染中是有用的抑制剂。本发明提供了一种含有式(I)的苯二氮卓化合物的药物组合物，以及制备该药物组合物的方法和使用该药物组合物治疗感染克罗斯特氏梭菌的患者的方法。本发明的化合物可以与额外的抗生素或抗毒素抗体药物结合使用。
• Synthesis and Evaluation of Vancomycin Aglycon Analogues That Bear Modifications in the N-Terminal <scp>d</scp>-Leucyl Amino Acid
  作者：Christine M. Crane、Dale L. Boger

  DOI：10.1021/jm801549b

  日期：2009.3.12

  The synthesis and biological evaluation of a series of vancomycin aglycon analogues bearing alternative residue 1 N-methyl-d-amino acids are described. The analogues were prepared to define whether H-bonding d-amino acids could improve the affinity for the model ligands N,N′-Ac2-l-Lys-d-Ala-d-Ala (2) and N,N′-Ac2-l-Lys-d-Ala-d-Lac (3) and improve antimicrobial activity against vancomycin-sensitive

  轴承替代残基1的一系列的万古霉素糖苷配基类似物的合成和生物学评价Ñ甲基d α-氨基酸中有描述。制备类似物以确定 H 键合d -氨基酸是否可以提高对模型配体N , N '-Ac 2 - l -Lys- d -Ala- d -Ala ( 2 ) 和N , N '-的亲和力Ac 2 - l -Lys- d -Ala- d -Lac ( 3) 并提高对万古霉素敏感或耐万古霉素细菌的抗菌活性。此外，一系列具有上的残留物1所附的亲核试剂（肼和胺）类似物的d α-氨基酸中描述检查它们与的C-末端酯反应的能力的是3，形成一个共价连接升-Lys- d -Ala 到天然产物类似物。
• Discovery of potent and selective β-homophenylalanine based dipeptidyl peptidase IV inhibitors
  作者：Jinyou Xu、Hyun O. Ok、Edward J. Gonzalez、Lawrence F. Colwell、Bahanu Habulihaz、Huaibing He、Barbara Leiting、Kathryn A. Lyons、Frank Marsilio、Reshma A. Patel、Joseph K. Wu、Nancy A. Thornberry、Ann E. Weber、Emma R. Parmee

  DOI：10.1016/j.bmcl.2004.06.099

  日期：2004.9

  equipotent thiazolidide 9. Extensive SAR studies on the phenyl ring of 9 led to the discovery of a novel series of potent and selective DP-IV inhibitors. Introduction of a fluorine at the 2-position proved to be crucial for the potency of this series. The 2,5-difluoro (22q) and 2,4,5-trifluoro (22t) analogues were potent inhibitors of DP-IV (IC(50)=270, 119nM, respectively).

  内部筛选铅β-氨基酰基脯氨酸8的修饰得到了等价的噻唑烷化物9。对9的苯环的广泛SAR研究导致发现了一系列新的有效的和选择性的DP-IV抑制剂。事实证明，在2位上引入氟对于该系列的效能至关重要。2,5-二氟（22q）和2,4,5-三氟（22t）类似物是DP-IV的有效抑制剂（分别为IC（50）= 270、119nM）。
• Compounds That Inhibit Replication Of Human Immunodeficiency Virus
  申请人：Balzarini Maria Rene Jan

  公开号：US20080076824A1

  公开（公告）日：2008-03-27

  The present invention relates to the discovery of a novel class of compounds that inhibit the replication of human immunodeficiency virus (HIV) and approaches to identify these compounds. More specifically, it has been found that enzymatically prepared alpha-hydroxyglycinamide and synthetically prepared alpha-hydroxyglycinamide inhibit the replication of HIV in human serum. Embodiments include methods to identify modified glycinamide compounds that inhibit HUV, methods to isolate and synthesize modified glycinamide compounds, and therapeutic compositions comprising these compounds.

  本发明涉及一种新型化合物类别的发现，该类化合物能够抑制人类免疫缺陷病毒（HIV）的复制，并提供了鉴定这些化合物的方法。具体来说，发现经酶法制备的α-羟基甘氨酰胺和人工合成的α-羟基甘氨酰胺能够抑制HIV在人血清中的复制。实施例包括鉴定抑制HUV的改性甘氨酰胺化合物的方法，分离和合成改性甘氨酰胺化合物的方法，以及包含这些化合物的治疗组合物。
• SERINE PROTEASE INHIBITORS
  申请人：Steinmetzer Torsten

  公开号：US20130267467A1

  公开（公告）日：2013-10-10

  The invention provides methods of making and using compounds of the formula shown, which are inhibitors of human plasmin and plasma kallikrein. (Formula I) The compounds are useful for the prevention of blood loss, and as components of fibrin adhesives.

  本发明提供了制备和使用式子I所示的化合物的方法，这些化合物是人体纤溶酶和血浆卡利肌酶的抑制剂。这些化合物可用于预防失血，并作为纤维蛋白黏合剂的组分。