芴甲氧羰基-3-(2-萘)-D-丙氨酸 | 138774-94-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 芴甲氧羰基-3-(2-萘)-D-丙氨酸
• 中文别名: N-芴甲氧羰基-3-(2-萘基)-D-丙氨酸；FMOC-D-3-(2-萘基)-丙氨酸；Fmoc-D-β-萘基苯丙氨酸；芴甲氧羰基-D-2-萘丙氨酸；Fmoc-3-(2-萘基)-D-丙氨酸；N-芴甲氧羰基-D-3-(2-萘基)-丙氨酸；Fmoc-D-2-萘丙氨酸；芴甲氧羰基-3-(2-萘基)-D-丙氨酸；Fmoc-2-D-Nal-OH；Fmoc-D-2-Nal-OH
• 英文名称: N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine
• 英文别名: Fmoc-D-(2)Nal-OH；Fmoc-D-Nal(2')-OH；Fmoc-3-(2'-naphthyl)-D-alanine；Fmoc-D-Nal-OH；Fmoc-D-Nal(2')；Fmoc-nal-OH；Fmoc-3-(2-naphthyl)-D-alanine；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-naphthalen-2-ylpropanoic acid
• CAS: 138774-94-4
• 化学式: C₂₈H₂₃NO₄
• mdl: MFCD00077044
• 分子量: 437.495
• InChiKey: JYUTZJVERLGMQZ-AREMUKBSSA-N

物化性质

• 熔点：
  191 °C
• 沸点：
  549.64°C (rough estimate)
• 密度：
  1.2227 (rough estimate)
• 溶解度：
  氯仿（少量，超声处理）、DMF（少量，超声处理）、DMSO（少量溶解）
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会发生分解，目前未发现有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.142
• 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
• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  29242990
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封，在2 ºC至-8 ºC下保存

SDS

Name:	(R)-N-FMOC-2-Naphthylalanine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	N-(9-Fluorenylmethoxycarbonyl)-2-Naphthyl-D-Alanine
CAS:	138774-94-4

Section 1 - Chemical Product MSDS Name:(R)-N-FMOC-2-Naphthylalanine 95% (98% E.E.) Material Safety Data Sheet
Synonym:N-(9-Fluorenylmethoxycarbonyl)-2-Naphthyl-D-Alanine

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
138774-94-4	(R)-N-FMOC-2-Naphthylalanine	95%	unlisted

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

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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.

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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.

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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.

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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.

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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.

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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# 138774-94-4: 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.

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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: 220.6 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: C28H23NO4
Molecular Weight: 437.49

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 138774-94-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-N-FMOC-2-Naphthylalanine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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

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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.

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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# 138774-94-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 138774-94-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 138774-94-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

Fmoc-3-(2-萘基)-D-丙氨酸是一种氨基酸衍生物，可用作医药中间体，用于构建棘白菌素B的母核。棘白菌素B是一种一线药物，主要用于治疗侵袭性真菌感染。此外，它还被用于制备西曲瑞克及其盐类化合物。西曲瑞克是一种注射用促性腺激素释放激素（GnRH）拮抗剂，常用于辅助生殖技术以帮助受孕，并在治疗某些对激素敏感的肿瘤方面也有显著效果，如子宫肌瘤、子宫内膜异位症和子宫内膜变薄。

反应信息

• 作为反应物：
  描述：

  芴甲氧羰基-3-(2-萘)-D-丙氨酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 、 mercury dichloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (4-{[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-[(R)-2-(N',N''-dicyclohexyl-guanidino)-3-naphthalen-2-yl-propionyl]-amino}-benzyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Nonpeptide bradykinin antagonist analogs based on a model of a Sterling-Winthrop nonpeptide bradykinin antagonist overlapped with cyclic hexapeptide bradykinin antagonist peptides

  摘要：

  A proposed overlap between cyclic hexapeptide Bradykinin antagonists and nonpeptide Bradykinin antagonists is discussed. Structural variations on both the peptides and nonpeptides support the proposed overlap based on an increase or decrease in the biological activities of the antagonists. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00328-4

文献信息

• Design and synthesis of a library of tertiary amides: Evaluation as mimetics of the melanocortins’ active core
  作者：Felikss Mutulis、Jana Kreicberga、Sviatlana Yahorava、Ilze Mutule、Larisa Borisova-Jan、Aleh Yahorau、Ruta Muceniece、Sandra Azena、Santa Veiksina、Ramona Petrovska

  DOI：10.1016/j.bmc.2007.06.003

  日期：2007.9.1

  acceptable results. According to this approach an efficient formation of Schiff bases was achieved in the presence of TiCl(4). Substances were isolated by reversed phase chromatography; in some cases isomers were additionally separated by chiral chromatography on Chirobiotic T. When tested on human recombinant melanocortin receptors all the tertiary amides showed some binding affinities; for the highest affinity

  在固相上制备了201种叔酰胺。将二胺偶联到活化的羧化王聚合物上，并使所得的聚合物取代的苄氧羰基保护的二胺与原甲酸三甲酯中的醛或酮反应，得到树脂连接的席夫碱。然后将偶联的树脂通过在4％的乙酸/原甲酸三甲酯中的氰基硼氢化钠还原为仲胺，然后在PyBroP和二异丙基乙胺的存在下用羧酸酰化。在清除剂（主要是1，2-乙二硫醇）存在下，通过三氟乙酸从树脂上裂解叔酰胺。当制备吲哚衍生物时，与连接体片段发生平行烷基化，得到2-（4-羟基苄基）-吲哚的衍生物作为副产物。在上述方法未给出可接受的结果的情况下，标题化合物的溶液合成或液相/固相混合制备被证明是有利的。根据这种方法，在TiCl（4）存在的情况下实现了席夫碱的有效形成。物质经反相色谱分离。在某些情况下，还可以通过在Chirobiotic T上进行手性色谱分离来分离异构体。在人重组黑皮质素受体上进行测试时，所有叔酰胺都表现出一定的结合亲和力。对于具有最高
• Human Somatostatin Receptor Specificity of Backbone-Cyclic Analogues Containing Novel Sulfur Building Units
  作者：Sharon Gazal、Garry Gelerman、Ofer Ziv、Olga Karpov、Pninit Litman、Moshe Bracha、Michel Afargan、Chaim Gilon

  DOI：10.1021/jm0100281

  日期：2002.4.1

  hormone but not of insulin release. We report the synthesis, bioactivity, and structure-activity relationship studies of compounds related to 1. In these analogues, the lactam bridge of 1 was replaced by a backbone disulfide bridge. We present a novel approach for conformational constraint of peptides by utilizing sulfur-containing building units for on-resin backbone cyclization. These disulfide backbone

  生长抑素14（somatostatin）及其临床可用的类似物奥曲肽，兰瑞肽和伐普肽是生长激素，胰岛素和胰高血糖素释放的有效抑制剂。最近，描述了一种具有体内内分泌选择性的新型骨干环生长抑素类似物c（GABA-Phe-Trp-（D）Trp-Lys-Thr-Phe-GlyC3-NH（2））（类似物1，PTR 3173）。这种长效八肽对人重组生长抑素受体（hsst）hsst2，hsst4和hsst5具有高亲和力。其新颖的结合特性可有效抑制体内生长激素，但不能抑制胰岛素释放。我们报告了与1相关的化合物的合成，生物活性和构效关系研究。在这些类似物中，1的内酰胺桥被骨架二硫键取代。我们提出了一种新的方法，通过利用含硫的建筑单元对树脂骨架骨架化肽的构象约束。如在各种酶混合物中测试的，这些1的二硫键主链环状类似物显示出显着的代谢稳定性。受体结合测定揭示了与它们的原型相比，这些类似物的不同的受体选择性特征。发
• Counterion exchange process for peptides
  申请人：Tovi Avi

  公开号：US20060148699A1

  公开（公告）日：2006-07-06

  The invention encompasses a process for purifying a peptide comprising loading a peptide onto a RP-HPLC column; washing the column with an aqueous solution of a pharmaceutically acceptable counterion salt; and eluting the peptide from the column with a solvent mixture of a organic solvent and an acid of the pharmaceutically acceptable counterion, wherein the aqueous solution has a pH of at least about 6.

  这项发明涵盖了一种纯化肽的过程，包括将肽加载到RP-HPLC柱上；用药用可接受的对离子盐的水溶液冲洗柱；并用含有有机溶剂和药用可接受的对离子的酸的溶剂混合物从柱中洗脱肽，其中水溶液的pH至少约为6。
• [EN] PEPTIDOMIMETICS FOR IMAGING THE GHRELIN RECEPTOR<br/>[FR] PEPTIDOMIMÉTIQUES POUR IMAGER LE RÉCEPTEUR DE LA GHRÉLINE
  申请人：LONDON HEALTH SCI CT RES INC

  公开号：WO2016191865A1

  公开（公告）日：2016-12-08

  ABSTRACT The present invention concerns compositions comprising and methods of identification and use of imaging agents. The imaging agents comprise a growth hormone secretagogues having a conjugated fluoride. The imaging agents of the present invention may be used for detection, diagnosis and/or staging of prostate or other forms of cancer, and may also be used for cardiac disease.

  摘要 本发明涉及包含成分的组合物，以及用于识别和使用成像剂的方法。这些成像剂包括具有共轭氟化物的生长激素分泌素。本发明的成像剂可用于前列腺或其他形式的癌症的检测、诊断和/或分期，也可用于心脏疾病。
• METHOD FOR INHIBITING INFLAMMATION and PRO-INFLAMMATORY CYTOKINE/CHEMOKINE EXPRESSION USING A GHRELIN ANALOGUE
  申请人：Ipsen Pharma S.A.S.

  公开号：US20160206700A1

  公开（公告）日：2016-07-21

  The present invention provides a method of ameliorating inflammation, inhibiting proinflammatory cytokine and/or chemokine expression and treating various diseases and/or conditions incidental to the onset of inflammation, in a subject in need of treatment for such conditions, by administering select analogues of native hGhrelin.

  本发明提供了一种改善炎症、抑制促炎细胞因子和/或趋化因子表达以及治疗与炎症发作相关的各种疾病和/或病况的方法，通过给予选择性的天然hGhrelin类似物来治疗需要治疗此类病况的受试者。