Boc-L-3-溴苯丙氨酸 | 82278-73-7

• 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: Boc-L-3-溴苯丙氨酸
• 中文别名: N-Boc-3-溴-L-苯基丙氨酸；叔丁氧羰基-3-溴苯基-L-丙氨酸；N-BOC-L-3-溴苯丙氨酸
• 英文名称: (2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid
• 英文别名: (S)-3-(3-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid；(S)-3-(3-bromophenyl)-2-((tert-butoxycarbonyl)amino)propionic acid；N-tert-butoxycarbonyl-L-3-bromophenylalanine；(S)-N-boc-3-bromophenylalanine；(2S)-3-(3-bromophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 82278-73-7
• 化学式: C₁₄H₁₈BrNO₄
• 分子量: 344.205
• InChiKey: FBUDYESOPLBQIR-NSHDSACASA-N

物化性质

• 熔点：
  106.1°C
• 沸点：
  475.3±40.0 °C(Predicted)
• 密度：
  1.5311 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S24/25
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存储于0℃阴凉干燥处。

SDS

Name:	(S)-N-BOC-3-Bromophenylalanine, 95%, (98% E.E.) Material Safety Data Sheet
Synonym:	N-tert-Butoxycarbonyl-3-Bromophenyl-L-Alanine.
CAS:	82278-73-7

Section 1 - Chemical Product MSDS Name: (S)-N-BOC-3-Bromophenylalanine, 95%, (98% E.E.) Material Safety Data Sheet
Synonym: N-tert-Butoxycarbonyl-3-Bromophenyl-L-Alanine.

---

SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
82278-73-7	(S)-N-BOC-3-Bromophenylalanine	95%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW The toxicological properties of this material have not been fully investigated. Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

SECTION 4 - FIRST AID MEASURES
Eyes:
Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

---

SECTION 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

SECTION 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation.

---

SECTION 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

SECTION 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 82278-73-7: Personal Protective Equipment
Eyes:
Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES
Physical State: Solid
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 106.1 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C14H18BrNO4
Molecular Weight: 344.21

---

SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported

---

SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 82278-73-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-N-BOC-3-Bromophenylalanine - Not listed by ACGIH, IARC, or NTP.

---

SECTION 12 - ECOLOGICAL INFORMATION

---

SECTION 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations.

---

SECTION 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material.

---

SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases: S 24/25 Avoid contact with skin and eyes. WGK (Water Danger/Protection) CAS# 82278-73-7: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 82278-73-7 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 82278-73-7 is not listed on the TSCA inventory. It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 1/16/2002 Revision #2 Date: 10/05/2004 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

Boc-Phe(3-Br)-OH是一种含有三氟乙酰氧基和3-溴苯基的苯丙氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  Boc-L-3-溴苯丙氨酸 在 盐酸 、 4-二甲氨基吡啶 、 copper(l) iodide 、 甲酸 、 palladium 10% on activated carbon 、 sodium methansulfinate 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 L-脯氨酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.67h， 生成 立他司特
  参考文献：
  名称：

  [EN] LFA-1 INHIBITOR AND POLYMORPH THEREOF
  [FR] INHIBITEUR DE LFA-1 ET POLYMORPHE DE CELUI-CI

  摘要：

  公开了化合物的制备和纯化方法、其中间体、多晶型及相关化合物。还公开了该化合物的制剂以及在治疗LFA-1介导疾病中的用途。

  公开号：

  WO2014018748A1
• 作为产物：
  描述：

  3-溴肉桂酸 在 recombinant cyanobacterium Anabaena variabilis phenylalanine ammonia lyase 、 氨基甲酸铵 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.33h， 生成 Boc-L-3-溴苯丙氨酸
  参考文献：
  名称：

  使用氨基甲酸铵作为氨源，增强丙烯酸对映体纯的卤代苯丙氨酸的生物催化生产†

  摘要：

  利用蓝细菌苯丙氨酸氨裂合酶（PAL）和氨基甲酸铵反应缓冲液的新型组合，已开发出一种与工业相关的强化方法，用于生产对映纯的卤代苯丙氨酸。该工艺的STYs大于200 g L -1 d -1，ee≥98 ％，简化了催化剂/反应缓冲液的制备和后处理。

  DOI：

  10.1039/c6cy00855k

文献信息

• [EN] PHOSPHONIC ACID DERIVATES AND THEIR USE AS P2Y12 RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS D'ACIDE PHOSPHONIQUE ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DU RÉCEPTEUR P2Y12
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2009069100A1

  公开（公告）日：2009-06-04

  The invention relates to 2-phenyl-pyrimidine derivatives containing a phosphonic acid motif and their use as P2Y12 receptor antagonists in the treatment and/or prevention of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cerebrovascular diseases or conditions associated with platelet aggregation, including thrombosis in humans and other mammals. (I).

  这项发明涉及含有膦酸基团的2-苯基嘧啶衍生物，以及它们作为P2Y12受体拮抗剂在治疗和/或预防外周血管、内脏-、肝脏和肾脏血管、心血管和脑血管疾病或与血小板聚集有关的疾病或状况中的使用，包括人类和其他哺乳动物中的血栓形成。（I）。
• Interaction of Papain-like Cysteine Proteases with Dipeptide-Derived Nitriles
  作者：Reik Löser、Klaus Schilling、Elke Dimmig、Michael Gütschow

  DOI：10.1021/jm050686b

  日期：2005.12.1

  were introduced, and systematic fluorine, bromine, and phenyl scans for phenylalanine in the P2 position were performed. Moreover, the N-terminal protection was varied. Kinetic investigations were carried out with cathepsin L, S, and K as well as papain. Changes in the backbone structure of the parent N-(tert-butoxycarbonyl)-phenylalanyl-glycine-nitrile (16), such as the introduction of an R-configured

  制备一系列44个在P2位具有各种氨基酸和在P1位具有甘氨酸的二肽腈，并将其评估为半胱氨酸蛋白酶的抑制剂。关于P2-S2相互作用对酶抑制剂复合物形成的重要贡献，重点是将结构多样性引入P2侧链。引入了非蛋白氨基酸，并进行了系统的氟，溴和苯基扫描，以检测P2位置的苯丙氨酸。而且，N-末端保护是多种多样的。使用组织蛋白酶L，S和K以及木瓜蛋白酶进行动力学研究。母体N-（叔丁氧羰基）-苯丙氨酰基-甘氨酸-腈的骨架结构变化（16），例如将R构型的氨基酸或氮杂氨基酸引入P2以及P1氮的甲基化，会导致亲和力的急剧下降。示例性地，16的氰基被醛或甲基酮官能团取代。关于靶酶的底物特异性，讨论了构效关系。
• Design, synthesis and stepwise optimization of nitrile-based inhibitors of cathepsins B and L
  作者：Lorenzo Cianni、Fernanda Dos Reis Rocho、Vinícius Bonatto、Felipe Cardoso Prado Martins、Jerônimo Lameira、Andrei Leitão、Carlos A. Montanari、Anwar Shamim

  DOI：10.1016/j.bmc.2020.115827

  日期：2021.1

  Human cathepsin B (CatB) is an important biological target in cancer therapy. In this work, we performed a knowledge-based design approach and the synthesis of a new set of 19 peptide-like nitrile-based cathepsin inhibitors. Reported compounds were assayed against a panel of human cysteine proteases: CatB, CatL, CatK, and CatS. Three compounds (7h, 7i, and 7j) displayed nanomolar inhibition of CatB

  人组织蛋白酶 B (CatB) 是癌症治疗中的重要生物学靶点。在这项工作中，我们采用了一种基于知识的设计方法，并合成了一组新的 19 种肽样腈基组织蛋白酶抑制剂。针对一组人半胱氨酸蛋白酶对报告的化合物进行了分析：CatB、CatL、CatK 和 CatS。三种化合物（7h、7i和7j）显示出对 CatB 的纳摩尔抑制以及对 CatK 和 CatL 的选择性。的选择性通过使用的组合来实现对位联苯环在P 3，卤代苯丙氨酸P 2和Thr-O-BZ组在P 1。同样地，化合物7I和7J在所研究的酶组中显示出选择性 CatB 抑制作用。我们还描述了一个成功的例子，用生物等排置换磺酰胺 [ 7e  →  6b ]的酰胺键，我们观察到 CatB 的亲和力和选择性增加，同时降低了化合物的亲脂性 (ilogP)。我们基于知识的设计方法和各自的结构-活性关系为治疗相关组织蛋白酶的特定配体-靶标相互作用提供了见解。
• [EN] THIOPENE-BASED TRICYCLIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME<br/>[FR] COMPOSÉS TRICYCLIQUES À BASE DE THIOPÈNE ET COMPOSITIONS PHARMACEUTIQUES RENFERMANT LESDITS COMPOSÉS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003084959A1

  公开（公告）日：2003-10-16

  Compounds having the formula (I), and pharmaceutically-acceptable salts, hydrates and prodrugs thereof, are useful as anti-inflammatory agents, in which R1, R2, and R3 are hydrogen, halogen, alkyl, or perfluoroalkyl; R4 is an optionally substituted alkyl or cycloalkyl group; X is a linker; A is an aryl, heteroaryl, heterocycle, cycloalkyl, or is absent; and R7 is a substituent on A as defined in the specification.

  具有公式(I)的化合物，以及其中所述化合物的药物可接受的盐、水合物和前药，作为抗炎剂是有用的，其中R1、R2和R3是氢、卤素、烷基或全氟烷基；R4是可选地取代的烷基或环烷基团；X是连接基；A是芳基、杂芳基、杂环、环烷基，或是缺失的；R7是如说明书中定义的A上的取代基。
• Chemical profiling of HIV-1 capsid-targeting antiviral PF74
  作者：Lei Wang、Mary C. Casey、Sanjeev Kumar V. Vernekar、Ha T. Do、Rajkumar Lalji Sahani、Karen A. Kirby、Haijuan Du、Atsuko Hachiya、Huanchun Zhang、Philip R. Tedbury、Jiashu Xie、Stefan G. Sarafianos、Zhengqiang Wang

  DOI：10.1016/j.ejmech.2020.112427

  日期：2020.8

  herein the design, synthesis, and evaluation of a large number of PF74 analogs aiming to provide a comprehensive chemical profiling of PF74 and advance the understanding on its detailed binding mechanism and pharmacophore. The analogs, containing structural variations mainly in the aniline domain and/or the indole domain, were assayed for their effect on stability of CA hexamers, antiviral activity,

  HIV-1 的衣壳蛋白 (CA) 通过组装成功能性衣壳核心、控制脱壳和进入核的动力学以及与各种宿主因子相互作用，在病毒复制周期的多个步骤中发挥重要作用。靶向 CA 是一种有吸引力但尚未开发的抗病毒方法。在所有已知的靶向 CA 的小分子化学型中，拟肽 PF74 特别有趣，因为它与一些重要宿主因子使用的相同口袋结合，从而产生非常理想的抗病毒表型。然而，PF74 的进一步开发需要了解其药效团并减轻其较差的代谢稳定性。我们在此报告设计、合成、和评估大量 PF74 类似物，旨在提供 PF74 的全面化学分析，并促进对其详细结合机制和药效团的理解。分析了主要在苯胺结构域和/或吲哚结构域中包含结构变异的类似物对 CA 六聚体稳定性、抗病毒活性和细胞毒性的影响。还测试了选定的类似物在肝微粒体中的代谢稳定性，单独或在 CYP3A 抑制剂存在的情况下。总的来说，我们的研究确定了重要的药效团元素并揭示了 PF74