(alphaS)-alpha-[[苄氧羰基]氨基]-2-萘丙酸 | 65365-16-4

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (alphaS)-alpha-[[苄氧羰基]氨基]-2-萘丙酸
• 中文别名: (S)-N-苄氧羰基--beta-萘基丙氨酸；(ALPHAS)-ALPHA-[[苄氧羰基]氨基]-2-萘丙酸
• 英文名称: N-benzyloxycarbonyl-L-2-naphthylalanine
• 英文别名: Z-Nal-OH；N-Cbz-L-(2-naphthyl)alanine；L-N-benzyloxycarbonyl-3-(2-naphthyl)alanine；(S)-N-Cbz-2-naphthylalanine；N-benzyloxycarbonyl-β-(2-naphthyl)-L-alanine；N-(benzyloxycarbonyl)-3-(2-naphthyl)-L-alanine；Z-L-(2-naphthyl)-alanine；Z-2-Nal-OH；(2S)-3-naphthalen-2-yl-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 65365-16-4
• 化学式: C₂₁H₁₉NO₄
• 分子量: 349.386
• InChiKey: XBRPIBMAJOTVHG-IBGZPJMESA-N

物化性质

• 沸点：
  591.4±50.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-2-Nal-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-2-Nal-OH
CAS number: 65365-16-4

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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, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C21H19NO4
Molecular weight: 349.4

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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：

  (alphaS)-alpha-[[苄氧羰基]氨基]-2-萘丙酸 在 4-二甲氨基吡啶 、 氢氧化钾 、 四丁基硫酸氢铵 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 benzyl (2S)-1-[(2S)-2-[[(2S)-2-[(3S,4R)-3-hydroxy-5-methyl-4-[[(2S,3R)-3-[(2S)-2-[methyl(phenylmethoxycarbonyl)amino]-3-naphthalen-2-ylpropanoyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]hexanoyl]oxy-3-methylbutanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  玉兰素B类似物的全合成及生物学评价

  摘要：

  丹丹素A和B是一类海洋天然环二肽，其结构和生物活性与二羟肌酐密切相关。合成的坦丹更容易获得，从而加快了该抗肿瘤，抗病毒和免疫抑制化合物家族新的大环衍生物的制备。通过将大内酰胺化位点从Nst 1和Thr 6更改为Pro 4和N，O -Me 2 Tyr 5来优化先前报道的合成坦丹林的合成路线残留物导致反应产率的显着提高。使用这种新的合成方法，制备了tamandarin B的四个新的大环类似物，并评估了其抗癌活性。这些结果提供了进一步的见解，其坦丹林和双精胺的结构活性关系。

  DOI：

  10.1021/jo070412r
• 作为产物：
  描述：

  L-naphthylalanine methyl ester hydrochloride 在 sodium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 1.0h， 生成 (alphaS)-alpha-[[苄氧羰基]氨基]-2-萘丙酸
  参考文献：
  名称：

  肽脯氨酸硼酸作为蛋白酶体抑制剂的合成及生物活性

  摘要：

  基于脯氨酸硼酸作为药效基团在激酶抑制剂中的应用以及我们先前的研究结果，以脯氨酸硼酸为战斗部，使用了两个系列的肽脯氨酸硼酸，二肽脯氨酸硼酸（I）和三肽设计并合成了脯氨酸硼酸（II）。首先评估所有合成的化合物对MGC803细胞的生物学活性，然后选择最佳的化合物II-7来测试其在六种人类肿瘤细胞系上的抗肿瘤谱以及对三个亚基的蛋白酶体抑制作用。结果表明，系列II具有比系列I更好的生物学活性。化合物II-7在细胞和蛋白酶体模型中不仅表现出优异的生物学活性（IC 50值为nM），而且亚单位选择性也好得多。因此，脯氨酸硼酸作为战斗部在蛋白酶体抑制剂的设计中是合理的。

  DOI：

  10.1016/j.bmc.2017.05.049
• 作为试剂：
  描述：

  L-3-(2-萘基)-丙氨酸 、 sodium hydroxide 、 氯甲酸苄酯 在 乙醚 、 乙酸乙酯 、 水 、 Sodium sulfate-III 、 petroleum ether 、 (alphaS)-alpha-[[苄氧羰基]氨基]-2-萘丙酸 、 ( ii ) 、 四氢呋喃 作用下， 以 水 为溶剂， 反应 2.17h， 以to give 7.5 g of N-(benzyloxycarbonyl)-3-(2-naphthyl)-L-alanine of melting point 109°-111° C. (ii) A solution of 7.5 g of N-(benzyloxycarbonyl)-3-(2-naphthyl)-L-alanine in 20 ml of dry tetrahydrofuran的产率得到(alphaS)-alpha-[[苄氧羰基]氨基]-2-萘丙酸
  参考文献：
  名称：

  Amino acid derivatives

  摘要：

  式子为##STR1##的化合物及其药学上可接受的酸加盐可以抑制重要来源的蛋白酶，并可用作治疗或预防病毒感染的药物。它们可以按照通常已知的程序制造。

  公开号：

  US05446161A1

文献信息

• Optimization of Peptidomimetics as Selective Inhibitors for the β-Catenin/T-Cell Factor Protein–Protein Interaction
  作者：Zhen Wang、Min Zhang、Jin Wang、Haitao Ji

  DOI：10.1021/acs.jmedchem.9b00147

  日期：2019.4.11

  64 and 0.44 μM, respectively, and exhibit good selectivity for β-catenin/Tcf over β-catenin/E-cadherin and β-catenin/adenomatous polyposis coli (APC) PPIs. The 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2 H-tetrazolium (MTS) cell viability assays revealed that 56, the ethyl ester of 53, was more potent than 53 in inhibiting viability of most of the Wnt/β-catenin hyperactive

  β-catenin/ T细胞因子（Tcf）蛋白质-蛋白质相互作用（PPI）在β-catenin信号通路中起着至关重要的作用，而该信号通路在许多癌症和纤维化中均被过度激活。基于旨在靶向β-catenin的Tcf4 G13ANDE17结合位点的化合物1，进行了广泛的结构-活性关系研究。结果，发现化合物53和57分别破坏Ki-值为0.64和0.44μM的β-catenin/ Tcf PPI，并且相对于β-catenin/ E-cadherin和β-catenin/ E-cadherin表现出良好的选择性。 β-catenin/腺瘤性息肉病（APC）PPI。3-（4,5-二甲基噻唑-2-基）-5-（3-羧基甲氧基苯基）-2-（4-磺基苯基）-2 H-四唑（MTS）细胞活力测定显示56，53的乙酯，在抑制大多数Wnt /β-catenin过度活跃的癌细胞的生存力上，它比53更有效。进一步的基于细胞的研究表明56破坏了β-catenin/
• Synthesis and SAR Study of Novel Peptide Aldehydes as Inhibitors of 20S Proteasome
  作者：Yuheng Ma、Bo Xu、Yuan Fang、Zhenjun Yang、Jingrong Cui、Liangren Zhang、Lihe Zhang

  DOI：10.3390/molecules16097551

  日期：——

  (1) and 20S proteasomes, a new series of peptide aldehyde derivatives were designed and synthesized. Their ability to inhibit 20S proteasome was assayed. Among them, Cbz-Glu(OtBu)-Phe-Leucinal (3c), Cbz-Glu(OtBu)-Leu-Leucinal (3d), and Boc-Ser(OBzl)-Leu-Leucinal (3o) exhibited the most activity, which represented an order of magnitude enhancement compared with MG132 (2). The covalent docking protocol

  在分析MG101(1)和20S蛋白酶体晶体结构的基础上，设计合成了一系列新的肽醛衍生物。测定了它们抑制 20S 蛋白酶体的能力。其中，Cbz-Glu(OtBu)-Phe-Leucinal (3c)、Cbz-Glu(OtBu)-Leu-Leucinal (3d) 和 Boc-Ser(OBzl)-Leu-Leucinal (3o) 的活性最强，与 MG132 (2) 相比，这代表了一个数量级的增强。共价对接协议用于探索结合模式。讨论了肽醛抑制剂的构效关系。
• Synthesis and Conformation of Aromatic Cyclic Dipeptides. Cyclo(phenylalanyl)₂, Cyclo(1-naphthylalanyl)₂, and Cyclo(2-naphthylalanyl)₂
  作者：Syun Egusa、Jun Takagi、Masahiko Sisido、Yukio Imanishi

  DOI：10.1246/bcsj.59.2195

  日期：1986.7

  Cyclic dipeptides of aromatic amino acids, cyclo(l-phenylalanyl)2, cyclo(l-1-naphthylalanyl)2, and cyclo(l-2-naphthylalanyl)2 were synthesized and subjected to spectroscopic analyses using 1H NMR, absorption, circular dichroism (CD), fluorescence, and fluorescence-detected circular dichroism (FDCD). The 1H NMR data suggested that the 2,5-piperazinedione rings of the three cyclic dipeptides are in planar or nearly planar bowsplit boat-type conformation. The aromatic side groups of cyclo(1- and 2-naphthylalanyl)2’s were found to take asymmetric configurations, one naphthyl group being folded onto the 2,5-piperazinedione ring, the other being unfolded. Strong exciton couplet was observed in CD spectra of the three compounds. The signs of the exciton splitting were opposite in the two naphthyl cyclic dipeptides. Fluorescence spectra of the two naphthyl cyclic dipeptides showed no excimer emission. The absence of strong interchromophoric interaction in the lowest excited state was also suggested by the virtual coincidence of CD spectrum with FDCD spectrum. From the above spectroscopic data, probable conformations were proposed for the naphthyl cyclic dipeptides.

  合成了芳香族氨基酸的环二肽cyclo(l-苯丙氨酰)2、cyclo(l-1-萘丙氨酰)2和cyclo(l-2-萘丙氨酰)2，并利用1H NMR、吸收光谱、圆二色谱(CD)、荧光光谱和荧光检测圆二色谱(FDCD)进行了光谱分析。1H NMR数据显示，这三种环二肽的2,5-哌嗪二酮环处于平面或近似平面的弓形分叉船式构象。cyclo(1-和2-萘丙氨酰)2的芳香侧基被发现采取不对称构型，一个萘基团折叠在2,5-哌嗪二酮环上，另一个则展开。在这三种化合物的CD光谱中观察到了强耦合分裂。两种萘基环二肽的耦合分裂符号相反。两种萘基环二肽的荧光光谱中未显示环二聚体发射。最低激发态中缺乏强烈的色素间相互作用，这也通过CD光谱与FDCD光谱的几乎重合得以表明。根据上述光谱数据，为萘基环二肽提出了可能的构象。
• [EN] PEPTIDOMIMETIC INHIBITORS OF Β-CATENIN/TCF PROTEIN–PROTEIN INTERACTION<br/>[FR] INHIBITEURS PEPTIDOMIMÉTIQUES DE L'INTERACTION PROTÉINE-PROTÉINE B-CATÉNINE/TCF
  申请人：H LEE MOFFITT CANCER CT & RES

  公开号：WO2020118179A1

  公开（公告）日：2020-06-11

  Disclosed are inhibitors for the β-catenin/T-cell factor interaction. The inhibitors are selective for β-catenin/T-cell factor over β-catenin/phosphocadherin, and β- catenin/phosphoAPC interactions. Methods of using the disclosed compounds to treat cancer are also disclosed.

  披露了β-连环蛋白/ T细胞因子相互作用的抑制剂。这些抑制剂对β-连环蛋白/ T细胞因子相互作用具有选择性，而不影响β-连环蛋白/磷酸钙粘蛋白和β-连环蛋白/磷酸化APC相互作用。还披露了利用这些披露的化合物治疗癌症的方法。
• Proteasome regulation of NF-KB activity
  申请人：The President and Fellows of Harvard College

  公开号：US06660268B1

  公开（公告）日：2003-12-09

  Disclosed herein is a method for regulating the activity of NF-&kgr;B in an animal comprising contacting cells of the animal with certain proteasome inhibitors.

  本文揭示了一种调节动物体内NF-&kgr;B活性的方法，包括将动物的细胞与特定的蛋白酶体抑制剂接触。