N-(4-硝基苯磺酰)-L-苯丙氨酸 | 64501-87-7

• 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: N-(4-硝基苯磺酰)-L-苯丙氨酸
• 中文别名: N-(4-硝基苯基亚磺酰基)-L-苯丙氨酸
• 英文名称: 2-(4-nitrophenylsulphonamido)-3-phenylpropanoic acid
• 英文别名: ((4-nitrophenyl)sulfonyl)phenylalanine；N-nosyl-L-phenylalanine；N-nosyl-L-phenylalanine-OH；Nα-(4-nitrobenzenesulfonyl)-L-phenylalanine；N-(4-Nitrophenylsulfonyl)-L-phenylalanine；(2S)-2-[(4-nitrophenyl)sulfonylamino]-3-phenylpropanoic acid
• CAS: 64501-87-7
• 化学式: C₁₅H₁₄N₂O₆S
• 分子量: 350.352
• InChiKey: JVHRPLXWZFPXIJ-AWEZNQCLSA-N

物化性质

• 熔点：
  169 °C
• 沸点：
  582.7±60.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  常温常压下稳定，远离氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 海关编码：
  2935009090
• 储存条件：
  存放在密封容器内，并置于阴凉、干燥处。储存时请远离氧化剂和热源，避免阳光直射。

SDS

N-(4-Nitrophenylsulfonyl)-L-phenylalanine
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: N-(4-Nitrophenylsulfonyl)-L-phenylalanine

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: N-(4-Nitrophenylsulfonyl)-L-phenylalanine
Percent: >98.0%(T)
CAS Number: 64501-87-7
Chemical Formula: C15H14N2O6S

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
N-(4-Nitrophenylsulfonyl)-L-phenylalanine

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Section 5. FIRE-FIGHTING MEASURES
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: White - Slightly pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:169°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents] No data available
N-(4-Nitrophenylsulfonyl)-L-phenylalanine

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulfur oxides
products:

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Section 11. TOXICOLOGICAL INFORMATION
No data available
Acute Toxicity:
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
No data available
Reproductive toxicity:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Not listed
UN-No:

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
N-(4-Nitrophenylsulfonyl)-L-phenylalanine

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

N-(4-硝基苯基磺酰基)-L-苯丙氨酸是一种苯丙氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  N-(4-硝基苯磺酰)-L-苯丙氨酸 在 sodium 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氨 为溶剂， 反应 0.75h， 生成 S-2-苄基氮杂环丙烷
  参考文献：
  名称：

  Deprotection of Sulfonyl Aziridines

  摘要：

  The deprotection of the chiral N-sulfonyl aziridines 1-3 has been studied under different desulfonylation conditions. Two methods for the efficient deprotection of 2-benzyl-, 2-phenyl-, and 2-carboxyl-N-sulfonylaziridines were found. The desulfonylation with lithium and a catalytic amount of di-tert-butyl biphenyl in THF at -78 degrees C led to the corresponding NH aziridines with yields up to 85%. Alternatively, the desulfonylation could be carried out with magnesium in methanol under ultrasonic conditions. The latter proved to be avery mild method and afforded the desulfonylated aziridines with yields up to 75%, even when the 2-phenyl substituted aziridine 2 was the studied substrate. Furthermore, in all the cases studied, no racemization was observed in the chiral center of the aziridines.

  DOI：

  10.1021/jo9815296
• 作为产物：
  描述：

  L-苯丙氨酸 、 对硝基苯磺酰氯 在 碳酸氢钠 作用下， 以 水 为溶剂， 以81 %的产率得到N-(4-硝基苯磺酰)-L-苯丙氨酸
  参考文献：
  名称：

  新型芳基磺酰胺衍生物作为 NLRP3 炎症小体抑制剂用于潜在的癌症治疗

  摘要：

  NLRP3 炎性体是先天免疫的重要组成部分，可感知多种病原体和宿主衍生的分子。然而，它的异常激活与包括癌症在内的多种疾病的发病机制有关。在这项研究中，我们设计并合成了一系列芳基磺酰胺衍生物 (ASDs) 来抑制 NLRP3 炎性体。其中，化合物6c、7n和10在纳摩尔浓度下特异性抑制 NLRP3 激活，而不影响 NLRC4 和 AIM2 炎性体的激活。此外，我们证明这些化合物可减少体内白细胞介素 1β (IL-1β) 的产生并减弱黑色素瘤的生长。此外，肝微粒体的代谢稳定性研究了6c、7n和10以及小鼠中最有趣的化合物6c的血浆暴露情况。因此，我们生成了有效的 NLRP3 炎症小体抑制剂，可以在未来的药物化学和药理学研究中考虑，旨在开发一种新的 NLRP3 炎症小体驱动的癌症治疗方法。

  DOI：

  10.1021/acs.jmedchem.3c00175

文献信息

• The dimethylsulfoxonium methylide as unique reagent for the simultaneous deprotection of amino and carboxyl function of N-Fmoc-α-amino acid and N-Fmoc-peptide esters
  作者：Mariagiovanna Spinella、Rosaria De Marco、Emilia L. Belsito、Antonella Leggio、Angelo Liguori

  DOI：10.1016/j.tet.2012.12.052

  日期：2013.2

  The dimethylsulfoxonium methylide is described as a unique and useful reagent for the simultaneous deprotection of amino and carboxyl function of N-Fmoc-α-amino acid and N-Fmoc-peptide esters. The new methodology was applied successfully both to solution- and solid-phase peptide synthesis. The adopted methodology was extended successfully also to peptides containing amino acids bearing acid-sensitive

  二甲基亚砜基亚甲基被描述为用于同时脱去N -Fmoc-α-氨基酸和N -Fmoc-肽酯的氨基和羧基官能团的独特且有用的试剂。新方法已成功应用于溶液和固相肽合成。所采用的方法也成功地扩展到含有在侧链上带有酸敏感保护基的氨基酸的肽。此外，在N-Fmoc-二肽甲基酯与二甲基亚砜基甲基的脱保护反应中未观察到可测量的差向异构。
• HIV protease inhibitors based on amino acid derivatives
  申请人：——

  公开号：US20020151546A1

  公开（公告）日：2002-10-17

  A compound selected from the group consisting of a compound of formula I 1 a compound of formula II 2 and when the compound of formula I and II comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein R 1 , R 2 , Cx, n, R 3 , R 4 , R 5 , Y are as defined in the specification.

  从以下组中选择的化合物，其中化合物I的化合物，化合物II的化合物，以及当化合物I和II的化合物包括其氨基团的药用可接受铵盐，其中R1、R2、Cx、n、R3、R4、R5、Y的定义如规范中所述。
• Design and synthesis of potent hydroxamate inhibitors with increased selectivity within the gelatinase family
  作者：José María Zapico、Anna Puckowska、Kamila Filipiak、Claire Coderch、Beatriz de Pascual-Teresa、Ana Ramos

  DOI：10.1039/c4ob01516a

  日期：——

  Triazole-based inhibitors with high potency and selectivity for MMP-2 were obtained through a click chemistry approach.

  三唑基抑制剂通过点击化学方法获得，具有高效和选择性作用于MMP-2。
• Synthesis, characterization and in vitro antitrypanosomal activities of new carboxamides bearing quinoline moiety
  作者：David Izuchukwu Ugwu、Uchechukwu Chris Okoro、Narendra Kumar Mishra

  DOI：10.1371/journal.pone.0191234

  日期：——

  report herein the synthesis and antitrypanosomal activity of 24 new amide derivatives of 3-aminoquinoline, bearing substituted benzenesulphonamide. Nine of the new derivatives showed comparable antitrypanosomal activities at IC50 range of 1–6 nM (melarsoprol 5 nM). Compound 11n and 11v are more promising antitrypanosomal agents with IC50 1.0 nM than the rest of the reported derivatives. The novel compounds

  目前报道的抗胰锥虫药物的毒性和耐药性锥虫的出现突显了对开发新型抗锥虫药物的需求。我们在此报告了带有取代苯磺酰胺的3-氨基喹啉的24种新酰胺衍生物的合成和抗胰蛋白酶活性。九种新衍生物在IC 50范围为1-6 nM（美洛普罗5 nM）时显示出可比的抗锥虫活性。化合物11n和11v是较有希望的抗锥虫药物，比其余报道的衍生物具有IC 50 1.0 nM。新化合物显示出令人满意的预测物理化学性质，包括口服生物利用度，通透性和转运性质。
• Novel anti-inflammatory and analgesic agents: synthesis, molecular docking and <i>in vivo</i> studies
  作者：David Izuchukwu Ugwu、Uchechukwu Christopher Okoro、Pius Onyeoziri Ukoha、Astha Gupta、Sunday N. Okafor

  DOI：10.1080/14756366.2018.1426573

  日期：2018.1.1

  in vivo anti-inflammatory, analgesic and ulcerogenic activities. Molecular docking showed an excellent binding interaction of the synthesised compounds with the receptors, with 17c showing the highest binding energy (-12.50 kcal/mol). Compounds 17c and 17i inhibited carrageenan-induced rat paw oedema at 72, 76, and 80% and 64, 73, and 78% at 1 h, 2 h, and 3 h, respectively. In the analgesic activity

  合成了十二种带有苯并噻唑的苯磺酰胺和羧酰胺的新衍生物，并研究了它们的体内抗炎，镇痛和促溃疡活性。分子对接显示出合成化合物与受体的极佳结合相互作用，其中17c显示出最高的结合能（-12.50 kcal / mol）。化合物17c和17i分别在1 h，2 h和3 h抑制角叉菜胶诱导的大鼠爪水肿，分别为72％，76％和80％，64％，73％和78％。在镇痛活性实验中，化合物17c，17 g和17i在0.5小时后的ED50（µM / kg）为96、127和84。1小时后分别为102、134和72，2小时后分别为89、156和69 µM / kg，这与塞来昔布的156、72和70 µM / kg相当。活性最高的衍生物17c和17i的致溃疡指数分别为0.82和0.89，分别相当于塞来昔布的0.92。新衍生物的理化研究表明，它们不会出现口服生物利用度问题。