N-苄氧羰基-4-氟苯丙氨酸 | 17543-58-7

• 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-苄氧羰基-4-氟苯丙氨酸
• 英文名称: (S)-2-(((benzyloxy)carbonyl)amino)-3-(4-fluorophenyl)propanoic acid
• 英文别名: 2S-2-benzyloxycarbonylamino-2-(4-fluorophenylmethyl)-acetic acid；(2S)-3-(4-fluorophenyl)-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 17543-58-7
• 化学式: C₁₇H₁₆FNO₄
• 分子量: 317.317
• InChiKey: YJSNXFAVHKHBPV-HNNXBMFYSA-N

物化性质

• 熔点：
  158-160℃ (ethyl acetate ligroine )
• 沸点：
  515.8±50.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-P-Fluoro-Phe-OH
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: Z-P-Fluoro-Phe-OH
CAS number: 17543-58-7

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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, refrigerated.
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: C17H16FNO4
Molecular weight: 317.3

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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, hydrogen fluoride.

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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-苄氧羰基-4-氟苯丙氨酸 在 甲酸 、 palladium 10% on activated carbon 作用下， 以 甲醇 为溶剂， 生成 L-4-氟苯丙氨酸
  参考文献：
  名称：

  含卤化氨基酸的 BIM-23052 新类似物的合成、体外生物活性、水解稳定性和对接

  摘要：

  一种有效的生长抑素类似物，BIM-23052 (DC-23-99) d -Phe-Phe-Phe- d -Trp-Lys-Thr-Phe-Thr-NH 2, 已在 nM 浓度下建立了体外生长激素抑制活性。它还具有对一些生长抑素受体的高亲和力的特点，这些受体主要分布在许多肿瘤细胞的细胞膜中。在此，我们报告了使用标准固相肽法 Fmoc/OtBu-strategy 合成一系列含有卤化 Phe 残基的 BIM-23052 类似物。在体外针对两种人类肿瘤细胞系（乳腺癌细胞系和肝细胞癌细胞系）以及人类非致瘤性上皮细胞系测试了这些化合物的细胞毒性作用。含有氟苯丙氨酸的类似物在 μM 范围内具有细胞毒性，因为含有 Phe (2-F) 的类似物对人肝细胞癌细胞系显示出更好的选择性。所提出的研究还表明，根据测试的细胞系，卤化 Phe 残基的积累不会增加细胞毒性。计算出的选择性指数揭示了母体化合物 BIM-23052

  DOI：

  10.1007/s00726-020-02915-3
• 作为产物：
  描述：

  DL-对氟苯丙氨酸 在 碳酸氢钠 、 sodium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 9.0h， 生成 N-苄氧羰基-4-氟苯丙氨酸
  参考文献：
  名称：

  含卤化氨基酸的 BIM-23052 新类似物的合成、体外生物活性、水解稳定性和对接

  摘要：

  一种有效的生长抑素类似物，BIM-23052 (DC-23-99) d -Phe-Phe-Phe- d -Trp-Lys-Thr-Phe-Thr-NH 2, 已在 nM 浓度下建立了体外生长激素抑制活性。它还具有对一些生长抑素受体的高亲和力的特点，这些受体主要分布在许多肿瘤细胞的细胞膜中。在此，我们报告了使用标准固相肽法 Fmoc/OtBu-strategy 合成一系列含有卤化 Phe 残基的 BIM-23052 类似物。在体外针对两种人类肿瘤细胞系（乳腺癌细胞系和肝细胞癌细胞系）以及人类非致瘤性上皮细胞系测试了这些化合物的细胞毒性作用。含有氟苯丙氨酸的类似物在 μM 范围内具有细胞毒性，因为含有 Phe (2-F) 的类似物对人肝细胞癌细胞系显示出更好的选择性。所提出的研究还表明，根据测试的细胞系，卤化 Phe 残基的积累不会增加细胞毒性。计算出的选择性指数揭示了母体化合物 BIM-23052

  DOI：

  10.1007/s00726-020-02915-3

文献信息

• Synthesis and structure–activity relationship of α-keto amides as enterovirus 71 3C protease inhibitors
  作者：Debin Zeng、Yuying Ma、Rui Zhang、Quandeng Nie、Zhengjie Cui、Yaxin Wang、Luqing Shang、Zheng Yin

  DOI：10.1016/j.bmcl.2016.02.039

  日期：2016.4

  α-Keto amide derivatives as enterovirus 71 (EV71) 3C protease (3Cpro) inhibitors have been synthesized and assayed for their biochemical and antiviral activities. structure–activity relationship (SAR) study indicated that small moieties were primarily tolerated at P1′ and the introduction of para-fluoro benzyl at P2 notably improved the potency of inhibitor. Inhibitors 8v, 8w and 8x exhibited satisfactory

  已经合成了作为肠病毒71（EV71）3C蛋白酶（3C pro）抑制剂的α-酮酰胺衍生物，并对其生化和抗病毒活性进行了测定。结构-活性关系（SAR）研究表明，在P1'处主要耐受小部分，在P2处引入对氟苄基可显着提高抑制剂的效力。抑制剂8v，8w和8x表现出令人满意的活性（IC 50分别 为1.32±0.26μM，1.88±0.35μM和1.52±0.31μM）和良好的CC 50值（CC 50  > 100μM）。α-酮酰胺可能是EV71 3C pro抑制剂的弹头的不错选择。
• [EN] PEPTIDOMIMETICS FOR THE TREATMENT OF CORONAVIRUS AND PICORNAVIRUS INFECTIONS<br/>[FR] PEPTIDOMIMÉTIQUES POUR LE TRAITEMENT D'INFECTIONS PAR CORONAVIRUS ET PICORNAVIRUS
  申请人：UNIV EMORY

  公开号：WO2020247665A1

  公开（公告）日：2020-12-10

  Compounds, compositions and methods for preventing, treating or curing a coronavirus, picornavirus, and/or Hepeviridae virus infection in human subjects or other animal hosts. Specific viruses that can be treated include enteroviruses. In one embodiment, the compounds can be used to treat an infection with a severe acute respiratory syndrome virus, such as human coronavirus 229E, SARS, MERS, SARS-CoV-1 (OC43), and SARS-CoV- 2. In another embodiment, the methods are used to treat a patient co-infected with two or more of these viruses, or a combination of one or more of these viruses and norovirus.

  用于预防、治疗或治愈人类主体或其他动物宿主中的冠状病毒、小RNA病毒和/或肝炎病毒感染的化合物、组合物和方法。可治疗的特定病毒包括肠病毒。在一个实施例中，这些化合物可用于治疗严重急性呼吸综合征病毒感染，如人类冠状病毒229E、SARS、MERS、SARS-CoV-1（OC43）和SARS-CoV-2。在另一个实施例中，这些方法用于治疗患有两种或更多这些病毒的患者，或一种或多种这些病毒与诺如病毒的组合。
• Synthesis and evaluation of potent, highly-selective, 3-aryl-piperazinone inhibitors of protein geranylgeranyltransferase-I
  作者：Hairuo Peng、Dora Carrico、Van Thai、Michelle Blaskovich、Cynthia Bucher、Erin E. Pusateri、Said M. Sebti、Andrew D. Hamilton

  DOI：10.1039/b517572k

  日期：——

  A series of compounds based on the carboxyl-terminal CAAL sequence of PGGTase-I substrates was designed and synthesized. Using piperazin-2-one as a semi-rigid scaffold, we have introduced critical pharmacophores in a well-defined arrangement to mimic the CAAL sequence. High potency and exceptional selectivity were obtained for inhibition of PGGTase-I with structures such as 45 and 70. Potency of this series of GGTIs was dependent on the presence of an L-leucine residue with a free carboxyl terminus, as well as an S configuration of the 3-aryl group. The selectivity was significantly enhanced by 5-methyl substitution on the imidazole ring and fluorine substitution on the 3-aryl group. Modification of the 6-position of the piperazinone scaffold was found to be unfavorable. Compounds 44 and 69, the corresponding methyl esters of 45 and 70, were found to selectively block processing of Rap1A by PGGTase-I in whole cells with IC50 values of 0.4 µM and 0.7 µM respectively.

  基于PGGTase-I底物的羧端CAAL序列，设计并合成了一系列化合物。我们利用哌嗪-2-酮作为半刚性骨架，在明确有序的排列中引入了关键的药效团，以模拟CAAL序列。对于抑制PGGTase-I，如45和70结构所展现，其活性高且选择性极佳。这一系列GGTIs的活性依赖于具有自由羧端的L-亮氨酸残基以及3-芳基的S构型。通过咪唑环上的5-甲基取代和3-芳基上的氟取代，其选择性显著提升。发现对哌嗪酮骨架的6位进行修饰是不利的。化合物44和69，即45和70的相应甲酯，分别以0.4 µM和0.7 µM的IC50值选择性地阻断PGGTase-I对Rap1A的细胞内加工。
• Compounds for enzyme inhibition
  申请人：Zhou Han-Jie

  公开号：US20070105786A1

  公开（公告）日：2007-05-10

  Peptide-based compounds including heteroatom-containing, three-membered rings efficiently and selectively inhibit specific activities of N-terminal nucleophile (Ntn) hydrolases associated with the proteasome. The peptide-based compounds include an epoxide or aziridine, and functionalization at the N-terminus. Among other therapeutic utilities, the peptide-based compounds are expected to display anti-inflammatory properties and inhibition of cell proliferation. Oral administration of these peptide-based proteasome inhibitors is possible due to their bioavailability profiles

  基于肽的化合物，包括含杂原子的三元环，能够高效且选择性地抑制与蛋白酶体相关的N-末端亲核（Ntn）水解酶的特定活性。这些基于肽的化合物包括环氧化物或氮杂环丙烷，并在N-末端进行官能化。除了其他治疗用途外，预计这些基于肽的化合物将显示抗炎性能和抑制细胞增殖。由于它们的生物利用度特性，这些基于肽的蛋白酶体抑制剂可以通过口服给药进行。
• [EN] PEPTIDOMIMETICS FOR THE TREATMENT OF NOROVIRUS INFECTION<br/>[FR] PEPTIDOMIMÉTIQUES POUR LE TRAITEMENT D'UNE INFECTION À NOROVIRUS
  申请人：UNIV EMORY

  公开号：WO2017197377A1

  公开（公告）日：2017-11-16

  The present invention is directed to compounds, compositions and methods for preventing, treating or curing Norovirus infection in human subjects or other animal hosts.

  本发明涉及用于预防、治疗或治愈人类主体或其他动物宿主中的诺如病毒感染的化合物、组合物和方法。