L-4-氰基苯丙氨酸 | 167479-78-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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: L-4-氰基苯丙氨酸
• 中文别名: L-对氰基苯丙氨酸
• 英文名称: 4-cyano-L-phenylalanine
• 英文别名: L-4-cyanophenylalanine；(S)-4-Cyanophenylalanine；(2S)-2-azaniumyl-3-(4-cyanophenyl)propanoate
• CAS: 167479-78-9
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: KWIPUXXIFQQMKN-VIFPVBQESA-N

物化性质

• 沸点：
  394.1±37.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  6.1
• 海关编码：
  2926909090
• 危险性防范说明：
  P301+P330+P331,P312,P280,P302+P352,P304+P340
• 危险性描述：
  H302+H312+H332
• 储存条件：
  -15°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: L-(S)-4-Cyanophenylalanine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H312: Harmful in contact with skin
H332: Harmful if inhaled
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
P312: Call a POISON CENTER or doctor/physician if you feel unwell

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Section 3. Composition/information on ingredients.
Ingredient name: L-(S)-4-Cyanophenylalanine
CAS number: 167479-78-9

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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.
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: C10H10N2O2
Molecular weight: 190.2

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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
UN Number: UN3439 Class: 6.1 Packing group: III
Proper shipping name: NITRILES, TOXIC, SOLID, N.O.S. (L-(S)-4-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：

  L-4-氰基苯丙氨酸 在 盐酸 、 氨 、 sodium carbonate 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.75h， 生成
  参考文献：
  名称：

  使用tech 99m标记的高效GPIIb / IIIa受体拮抗剂进行血栓成像。化学和初步生物学研究。

  摘要：

  用发射伽马射线的放射性核素进行放射性标记的血小板特异性化合物可能特别适用于血栓的体内无创检测。描述了肽的合成，所述肽是血小板聚集的有效抑制剂，并且包含放射性核素-99m的螯合剂。设计目标化合物的目的是，可以在金属配位位置明确的位置制备稳定的氧V（V）物种。采用了一种策略，其中药效基团-Arg-Gly-Asp-（RGD）或RGD模拟物被限制在一个环中，该环是通过半胱氨酸残基与N端氯乙酰基的S-烷基化而形成的。通过用精氨酸模拟物S-（3-氨基丙基）半胱氨酸和4-ami基苯基丙氨酸替代精氨酸来增强结合亲和力。通过合成包含两个或更多个含有受体结合区的环的低聚物，可以获得进一步的增强。看到的结合亲和力的增加超过了药效团的简单化学计量增加的预期。所描述的最有效的化合物具有约0.03 microM的IC50，可抑制人的血小板凝集。用tech 99m标记两个更有效的肽（P280和P748），并在犬血栓形成模型中进行评估。这项工作中制备的99m

  DOI：

  10.1021/jm950112e
• 作为产物：
  描述：

  对氰基溴化苄 在 盐酸 、 lithium hydroxide 、 sodium hydroxide 、 sodium ethanolate 作用下， 反应 77.25h， 生成 L-4-氰基苯丙氨酸
  参考文献：
  名称：

  使用tech 99m标记的高效GPIIb / IIIa受体拮抗剂进行血栓成像。化学和初步生物学研究。

  摘要：

  用发射伽马射线的放射性核素进行放射性标记的血小板特异性化合物可能特别适用于血栓的体内无创检测。描述了肽的合成，所述肽是血小板聚集的有效抑制剂，并且包含放射性核素-99m的螯合剂。设计目标化合物的目的是，可以在金属配位位置明确的位置制备稳定的氧V（V）物种。采用了一种策略，其中药效基团-Arg-Gly-Asp-（RGD）或RGD模拟物被限制在一个环中，该环是通过半胱氨酸残基与N端氯乙酰基的S-烷基化而形成的。通过用精氨酸模拟物S-（3-氨基丙基）半胱氨酸和4-ami基苯基丙氨酸替代精氨酸来增强结合亲和力。通过合成包含两个或更多个含有受体结合区的环的低聚物，可以获得进一步的增强。看到的结合亲和力的增加超过了药效团的简单化学计量增加的预期。所描述的最有效的化合物具有约0.03 microM的IC50，可抑制人的血小板凝集。用tech 99m标记两个更有效的肽（P280和P748），并在犬血栓形成模型中进行评估。这项工作中制备的99m

  DOI：

  10.1021/jm950112e

文献信息

• [EN] BACKBONE-CYCLIZED PEPTIDOMIMETICS<br/>[FR] PEPTIDOMIMÉTIQUES À SQUELETTE CYCLISÉ
  申请人：POLYPHOR AG

  公开号：WO2016162127A1

  公开（公告）日：2016-10-13

  Novel backbone-cyclized peptidomimetics of the general formula cyclo[-P1-P2-P3-P4-P5-P6-P7-P8-T1-T2-] (I) wherein the single elements T or P are α-amino acid residues connected in either direction which, depending on their positions in the chain, are as defined in the description and the claims, and salts thereof, have the property to modulate the GLP-1 receptor. They can be used as medicaments to treat, prevent, or delay the onset of diseases, disorders or conditions in which modulation of the human GLP-1 receptor is beneficial, such as type 2 diabetes. These backbone-cyclized peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.

  新型的骨架环化肽类似物的一般公式为cyclo[-P1-P2-P3-P4-P5-P6-P7-P8-T1-T2-]（I），其中单个元素T或P是α-氨基酸残基，以任一方向连接，根据它们在链中的位置，在描述和权利要求中定义，以及其盐，具有调节GLP-1受体的特性。它们可用作药物治疗、预防或延缓调节人类GLP-1受体有益的疾病、紊乱或病况，如2型糖尿病。这些骨架环化肽类似物可通过基于混合固相和溶液相合成策略的过程制造。
• Anti-angiogenic compounds
  申请人：Bradshaw W. Curt

  公开号：US20060205670A1

  公开（公告）日：2006-09-14

  The present invention provides AA targeting compounds which comprise AA targeting agent-linker conjugates which are linked to a combining site of an antibody. Various uses of the compounds are provided, including methods to treat disorders connected to abnormal angiogenesis.

  本发明提供了包括与抗体的结合位点连接的AA靶向剂-连接剂共轭物的AA靶向化合物。提供了化合物的各种用途，包括治疗与异常血管生成相关的疾病的方法。
• [EN] NOVEL HEPCIDIN MIMETICS AND USES THEREOF<br/>[FR] NOUVEAUX MIMÉTIQUES D'HEPCIDINE ET LEURS UTILISATIONS
  申请人：BAYER HEALTHCARE LLC

  公开号：WO2018128828A1

  公开（公告）日：2018-07-12

  The present invention relates to novel peptides acting as hepcidin mimetics, as well as analogues and derivatives thereof. The invention further relates to compositions comprising the peptides of the present invention, and to the use of the peptides in the prophylaxis and treatment of hepcidin-associated disorders, including prophylaxis and treatment of iron overload diseases such as hemochromatosis, iron-loading anemias such as thalassemia, and diseases being associated with ineffective or augmented erythropoiesis, as well as further related conditions and disorders described herein.

  本发明涉及作为赫普西定类似物的新型肽，以及其类似物和衍生物。该发明还涉及包含本发明肽的组合物，以及在预防和治疗赫普西定相关疾病中使用这些肽，包括预防和治疗铁过载疾病如血色病、铁负荷性贫血如地中海贫血，以及与效率低下或增强的红细胞生成相关的疾病，以及本文所述的进一步相关病症和疾病。
• [EN] AZASULFURYLPEPTIDE-BASED CD36 MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS CD36 À BASE D'AZASULFURYLPEPTIDES ET UTILISATIONS DE CEUX-CI
  申请人：RSEM LTD PARTNERSHIP

  公开号：WO2016029324A1

  公开（公告）日：2016-03-03

  Novel azasulfuryl-containing peptidomimetics capable of inhibiting CD36 activity are disclosed. Use of these azasulfuryl-containing peptidomimetics for the treatment of CD36-related diseases, disorders or conditions, including TLR2-mediated inflammatory disease, disorder or condition, and methods of obtaining such azasulfuryl-containing peptidomimetics, are also disclosed.

  揭示了能够抑制CD36活性的新型含氮硫酰基的肽类模拟物。还揭示了利用这些含氮硫酰基的肽类模拟物治疗与CD36相关的疾病、紊乱或状况，包括TLR2介导的炎症性疾病、紊乱或状况的用途，以及获取这种含氮硫酰基的肽类模拟物的方法。
• 12-EPI PLEUROMUTILINS
  申请人：NABRIVA THERAPEUTICS AG

  公开号：US20160332963A1

  公开（公告）日：2016-11-17

  A compound selected from 14-O-[((Alkyl-, cycloalkyl-, heterocycloalkyl-, heteoroaryl-, or aryl)-sulfanyl)-acetyl]-12-epi-mutilins, or 14-O-[((Alkyl-, cycloalkyl-, heterocycloalkyl-, heteoroaryl-, or aryl)-oxy)-acetyl]-12-epi-mutilins, wherein 12-epi-mutilin is characterized in that the mutilin ring at position 12 is substituted by two substituents, the first substituent at position 12 of the mutilin ring is a methyl group which methyl group has the inverse stereochemistry compared with the stereochemistry of the methyl group at position 12 of the naturally occurring pleuromutilin ring, the second substituent at position 12 of the mutilin ring is a hydrocarbon group comprising at least one nitrogen atom and all other substituents of the mutilin ring having the same stereochemistry compared with the stereochemistry of the substituents at the corresponding positions in the naturally occurring pleuromutilin ring; optionally in the form of a salt and/or solvate, wherein the naturally occurring pleuromutilin is of formula processes for the preparation of such compounds and their use as pharmaceuticals.

  从14-O-[((烷基、环烷基、杂环烷基、杂环芳基或芳基)-硫基)-乙酰基]-12-epi-木替林，或14-O-[((烷基、环烷基、杂环烷基、杂环芳基或芳基)-氧基)-乙酰基]-12-epi-木替林中选择的一种化合物，其中12-epi-木替林的特征在于木替林环在位置12被两个取代基取代，木替林环在位置12的第一个取代基是一个甲基基团，该甲基基团的立体化学与天然存在的普鲁木替林环在位置12的甲基基团的立体化学相反，木替林环在位置12的第二个取代基是一个含有至少一个氮原子的碳氢基团，木替林环的所有其他取代基与天然存在的普鲁木替林环中相应位置的取代基的立体化学相同；可选地以盐和/或溶剂的形式存在，其中天然存在的普鲁木替林的化学式为 制备这类化合物的方法以及它们作为药物的用途。