Boc-β-氰基-L-丙氨酸 | 45159-34-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 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: Boc-β-氰基-L-丙氨酸
• 中文别名: Β-氰基丙氨酸羟基；Boc-b-氰基苯胺
• 英文名称: (2S)-2-[(tert-butoxycarbonyl)amino]-3-cyanopropanoic acid
• 英文别名: Boc-Ala(CN)；L-N-Boc-β-cyanoalanine；N-α-(tert-butoxycarbonyl)-β-cyano-L-alanine；(S)-2-((tert-butoxycarbonyl)amino)-3-cyanopropanoic acid；(2S)-3-cyano-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-propanoic acid；2-(tert-butoxycarbonylamino)-3-cyanopropanoic acid；N-t-butoxycarbonyl-3-cyano-L-alanine；Boc-β-cyano-(L)-Ala-OH；(2S)-3-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 45159-34-0
• 化学式: C₉H₁₄N₂O₄
• 分子量: 214.221
• InChiKey: IVKMLPKBZQTAMQ-LURJTMIESA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  408.6±40.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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
• 危险品标志：
  Xi
• 安全说明：
  S36/37
• 危险类别码：
  R43
• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-beta-cyano-l-alanine
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-beta-cyano-l-alanine
CAS number: 45159-34-0

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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: C9H14N2O4
Molecular weight: 214.2

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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：

  Boc-β-氰基-L-丙氨酸 在 三乙胺 、 氯甲酸异丁酯 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以650 mg的产率得到tert-butyl [(2S)-1-cyano-3-hydroxypropan-2-yl]carbamate
  参考文献：
  名称：

  PARTIALLY SATURATED NITROGEN-CONTAINING HETEROCYCLIC COMPOUND

  摘要：

  公开号：

  EP2881384B1
• 作为产物：
  描述：

  BOC-L-天冬酰胺 在 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-β-氰基-L-丙氨酸
  参考文献：
  名称：

  氨基酸替代：间接合成含有硫天冬酰胺残基的肽的方法

  摘要：

  受保护的五肽Boc-Tan-Cys（PMB）-Pro-Leu-GlynH 2 1和相关的硫天冬酰胺基化合物是通过相应的β-氰基丙氨酰基前体经H 2 S / NH 3处理而间接制备的。硫天冬酰胺（Tan）衍生物的光学纯度通过两种不同的方法进行了评估。

  DOI：

  10.1016/s0040-4039(00)86771-4

文献信息

• Discovery of an Orally Active Series of Isoxazoline Glycoprotein IIb/IIIa Antagonists
  作者：Chu-Biao Xue、John Wityak、Thais M. Sielecki、Donald J. Pinto、Douglas G. Batt、Gary A. Cain、Michael Sworin、Arlene L. Rockwell、John J. Roderick、Shuaige Wang、Michael J. Orwat、William E. Frietze、Lori L. Bostrom、Jie Liu、C. Anne Higley、F. Wayne Rankin、A. Ewa Tobin、George Emmett、George K. Lalka、Jean Y. Sze、Susan V. Di Meo、Shaker A. Mousa、Martin J. Thoolen、Adrienne L. Racanelli、Elizabeth A. Hausner、Thomas M. Reilly、William F. DeGrado、Ruth R. Wexler、Richard E. Olson

  DOI：10.1021/jm960799i

  日期：1997.6.1

  Using isoxazoline XR299 (1a) as a starting point for the design of highly potent, long-duration GPIIb/IIIa antagonists, the effect of placing lipophilic substituents at positions alpha and beta to the carboxylate moiety was evaluated. Of the compounds studied, it was found that the n-butyl carbamate 24u exhibited superior potency and duration of ex vivo antiplatelet effects in dogs. Replacement of

  使用异恶唑啉XR299（1a）作为设计高效，长效GPIIb / IIIa拮抗剂的起点，评估了将亲脂性取代基置于羧酸酯部分的α和β处的效果。在所研究的化合物中，发现氨基甲酸正丁酯24u在狗中表现出优异的效力和离体抗血小板作用的持续时间。用可替代的碱性基团取代苯并胺丁-4-基部分，消除异恶唑啉立体中心，并改变异恶唑啉环的方向，导致效力和/或作用时间降低。
• [EN] CATHEPSIN C INHIBITORS<br/>[FR] INHIBITEURS DE CATHEPSINE C
  申请人：GLAXO GROUP LTD

  公开号：WO2011025799A1

  公开（公告）日：2011-03-03

  Disclosed are 3-aminopyrrolidines of Formula (I) having pharmacological activity, pharmaceutical compositions containing them, and methods for the treatment of diseases mediated by the cathepsin C enzyme such as chronic obstructive pulmonary disease.

  揭示了具有药理活性的式（I）的3-氨基吡咯烷，包含它们的药物组合物，以及用于治疗由cathepsin C酶介导的疾病（如慢性阻塞性肺病）的方法。
• [EN] ALBICIDIN DERIVATIVES, THEIR USE AND SYNTHESIS<br/>[FR] DÉRIVÉS D'ALBICIDINE, LEUR UTILISATION ET LEUR SYNTHÈSE
  申请人：TECH UNIVERSITÄT BERLIN

  公开号：WO2014125075A1

  公开（公告）日：2014-08-21

  The present invention relates to a antibiotically active compounds characterized by general formula (I), wherein X1, BB, BC, BD, BE and X2 are building blocks with D1, D2, D3, D4 or D5 being linkers which comprise carbon, sulphur, nitrogen, phosphor and/or oxygen atoms and which are covalently connecting the moities BA and BB, BB and BC, BC and BD, BD and BE and BE and BF, respectively, and wherein in particular the building block BC comprises an amino acid derivative. The invention relates further to said compounds for use in a method of treatment of diseases, in particular for use in a method of treatment of bacterial infections.

  本发明涉及一种抗生素活性化合物，其特征在于一般式（I），其中X1、BB、BC、BD、BE和X2是具有D1、D2、D3、D4或D5为连接物的构建块，该连接物包括碳、硫、氮、磷和/或氧原子，并以共价键连接BA和BB、BB和BC、BC和BD、BD和BE以及BE和BF的基团，特别是构建块BC包括氨基酸衍生物。该发明还涉及上述化合物用于治疗疾病的方法，特别是用于治疗细菌感染的方法。
• [EN] DIAZEPINOINDOLE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DERIVES DE DIAZEPINOINDOLE EN TANT QU'INHIBITEURS DE KINASE
  申请人：PFIZER

  公开号：WO2004063198A1

  公开（公告）日：2004-07-29

  Protein kinase, such as CHK-1, inhibiting tricyclic compounds of the following formula (wherein R2, R3 and R4 are as defined in the specification) pharmaceutical compositions containing effective amounts of said compounds or their salts are useful as a single agent or in combination with an anti-neoplastic agent or therapeutic radiation having an anti-neoplastic effect for treating diseases or conditions, such as cancers.

  蛋白激酶，如CHK-1，抑制以下式的三环化合物（其中R2、R3和R4如规范中定义）的药物组合物，含有所述化合物或其盐的有效量，可用作单一药剂或与抗肿瘤药剂或具有抗肿瘤效果的治疗放射剂结合，用于治疗疾病或病况，如癌症。
• Synthesis and Anti-Helicobacter pylori Activity of Pyloricidin Derivatives. I. Structure-activity Relationships on the Terminal Peptidic Moiety.
  作者：ATSUSHI HASUOKA、YUJI NISHIKIMI、YUTAKA NAKAYAMA、KEIJI KAMIYAMA、MASAFUMI NAKAO、KEN-ICHIRO MIYAGAWA、OSAMU NISHIMURA、MASAHIKO FUJINO

  DOI：10.7164/antibiotics.55.322

  日期：——

  The novel natural antibiotics pyloricidin A, B and C possess potent and highly selective antibacterial activity against Helicobacter pylori. In order to investigate the structure activity relationships for the terminal peptidic moiety, a series of pyloricidin B and pyloricidin C derivatives, bearing various amino acids in the moiety, were prepared and evaluated for their anti-H. pylori activity. The derivatives bearing α-D-, β- and γ-amino acids or peptidemimetics showed drastically decreased activity. On the other hand, the derivatives with α-L-amino acids were found to maintain the activity. Among the derivatives prepared in this work, the allylglycine derivative 2s showed the most potent anti-H. pylori activity, with an MIC value of less than 0.006μg/ml against H. pylori NCTC11637, which is 60-fold greater than the activity of the lead compound pyloricidin C.

  新型天然抗生素喷菌素A、B和C对幽门螺杆菌具有强效且高度选择性的抗菌活性。为了研究末端肽部分的结构-活性关系，制备了一系列含不同氨基酸的喷菌素B和喷菌素C衍生物，并评估了它们的抗幽门螺杆菌活性。含有α-D-、β-和γ-氨基酸或肽模拟物的衍生物显示出显著降低的活性。另一方面，含有α-L-氨基酸的衍生物被发现能保持活性。在本工作中制备的衍生物中，烯丙基甘氨酸衍生物2s表现出最强的抗幽门螺杆菌活性，对幽门螺杆菌NCTC11637的最低抑制浓度（MIC）值小于0.006μg/ml，比原始化合物喷菌素C的活性高出60倍。