BOC-L-焦谷氨酸乙酯 | 144978-12-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酸类衍生物
• 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-焦谷氨酸乙酯
• 中文别名: (S)-1-(叔丁氧羰基)-5-氧代吡咯烷-2-甲酸乙酯；(S)-1-Boc-5-氧代吡咯烷-2-甲酸乙酯；叔丁氧羰基-L-焦谷氨酸乙酯；N-Boc-L-焦谷氨酸乙酯；Boc-L-焦谷氨酸乙酯；N-(叔丁氧羰基)-L-焦谷氨酸乙酯；L-焦谷氨酸一乙脂；N-叔丁氧羰基-L-焦谷氨酸乙酯；1-Boc-L-焦谷氨酸乙酯；BOC-L-Pyr Oet
• 英文名称: (S)-ethyl N-tert-butoxycarbonylpyroglutamate
• 英文别名: (S)-1-tert-butyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate；1-(tert-butyl) 2-ethyl (S)-5-oxopyrrolidine-1,2-dicarboxylate；1-tert-butyl 2-ethyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate；ethyl N-Boc (S)-pyroglutamate；ethyl N-tert-butoxycarbonyl-L-pyroglutamate；1-(tert-butyl) 2‑ethyl (S)-5-oxopyrrolidine-1,2-dicarboxylate；Boc-L-pyroglutamic acid ethyl ester；Boc-pyr-oet；1-O-tert-butyl 2-O-ethyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate
• CAS: 144978-12-1
• 化学式: C₁₂H₁₉NO₅
• 分子量: 257.287
• InChiKey: YWWWGFSJHCFVOW-QMMMGPOBSA-N

物化性质

• 熔点：
  52.0 to 56.0 °C
• 沸点：
  375.0±35.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-Pyr-OEt
Synonyms: (S)-Ethyl-N-boc-pyroglutamate

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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: Boc-Pyr-OEt
CAS number: 144978-12-1

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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: C12H19NO5
Molecular weight: 257.3

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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.

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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

制备方法与用途

用途

BOC-L-焦谷氨酸乙酯是由焦谷氨酸衍生而来的化合物，用于合成各种药理化合物。它被广泛应用于合成HCV蛋白酶抑制剂和烷基肾素抑制剂。

反应信息

• 作为反应物：
  描述：

  BOC-L-焦谷氨酸乙酯 在 盐酸 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 lithium hydroxide monohydrate 、 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 palladium 10% on activated carbon 、 ammonium acetate 、 氢气 、 potassium acetate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 乙二醇甲醚 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 115.0h， 生成 维帕他韦
  参考文献：
  名称：

  氘代抗丙肝病毒活性化合物

  摘要：

  本发明涉及式I所代表的具有良好生物利用度的抗丙肝病毒化合物及其非毒性的药学上可接受的盐，该类化合物对所有基因型的HCV均有强效抑制作用。结构式I中，R1、R2、R3和R4各自独立选自于甲基(‑CH3)或氘代甲基(‑CD3)；X1、X2、X3、X4和X5分别为氢(H)或氘(D)；R1、R2、R3和R4中必须有一个为氘代甲基(‑CD3)或X1、X2、X3、X4和X5中必须有一个为氘(D)。

  公开号：

  CN107556324A
• 作为产物：
  描述：

  L-焦谷氨酸 在 4-二甲氨基吡啶 、 硫酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 BOC-L-焦谷氨酸乙酯
  参考文献：
  名称：

  L-γ-亚甲基谷氨酸酰胺叔丁酯和乙酯抗癌前药的合成及生物学评价

  摘要：

  在癌细胞中，谷氨酰胺分解是生物合成前体的主要来源。最近，人们在开发氨基酸类似物来抑制癌症中谷氨酰胺代谢方面做出了广泛的努力。我们的实验室最近发现了许多L -γ-亚甲基谷氨酸酰胺，在24年后抑制MCF-7、SK-BR-3和MDA-MB-231乳腺癌细胞的生长与他莫昔芬或奥拉帕尼一样有效。或72小时的治疗。这些化合物均不会抑制非恶性 MCF-10A 乳腺细胞的细胞生长。这些L -γ-亚甲基谷氨酸酰胺有望成为治疗多种乳腺癌亚型的新型疗法。在此，我们报告了这些L -γ-亚甲基谷氨酸酰胺的两个系列的叔丁酯和乙酯前药及其环状代谢物及其叔丁酯和乙酯对三种乳腺癌细胞系MCF的合成和评价-7、SK-BR-3 和 MDA-MB-231 以及非恶性 MCF-10A 乳腺细胞系。这些酯被发现可以抑制乳腺癌细胞的生长，但与L - γ-亚甲基谷氨酸酰胺相比，它们的效力较差。对L - γ-亚甲基谷氨酸酰胺先导物进行药代动力学

  DOI：

  10.1016/j.bmc.2022.117137

文献信息

• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Discovery, Structure−Activity Relationship, and Pharmacological Evaluation of (5-Substituted-pyrrolidinyl-2-carbonyl)-2-cyanopyrrolidines as Potent Dipeptidyl Peptidase IV Inhibitors
  作者：Zhonghua Pei、Xiaofeng Li、Kenton Longenecker、Thomas W. von Geldern、Paul E. Wiedeman、Thomas H. Lubben、Bradley A. Zinker、Kent Stewart、Stephen J. Ballaron、Michael A. Stashko、Amanda K. Mika、David W. A. Beno、Michelle Long、Heidi Wells、Anita J. Kempf-Grote、David J. Madar、Todd S. McDermott、Lakshmi Bhagavatula、Michael G. Fickes、Daisy Pireh、Larry R. Solomon、Marc R. Lake、Rohinton Edalji、Elizabeth H. Fry、Hing L. Sham、James M. Trevillyan

  DOI：10.1021/jm051283e

  日期：2006.6.1

  A series of (5-substituted pyrrolidinyl-2-carbonyl)-2-cyanopyrrolidine (C5-Pro-Pro) analogues was discovered as dipeptidyl peptidase IV (DPPIV) inhibitors as a potential treatment of diabetes and obesity. X-ray crystallography data show that these inhibitors bind to the catalytic site of DPPIV with the cyano group forming a covalent bond with the serine residue of DPPIV. The C5-substituents make various

  发现了一系列（5-取代的吡咯烷基-2-羰基）-2-氰基吡咯烷（C5-Pro-Pro）类似物作为二肽基肽酶IV（DPPIV）抑制剂，可用于治疗糖尿病和肥胖症。X射线晶体学数据表明，这些抑制剂与DPPIV的催化位点结合，其中氰基与DPPIV的丝氨酸残基形成共价键。C5取代基与酶发生各种相互作用，并影响抑制剂的效能，化学稳定性，选择性和PK特性。优化的类似物对亚纳摩尔的K（i）具有极强的效力，化学性质稳定，在血浆存在下几乎没有效力降低，并且对相关肽酶的选择性超过1,000倍。
• COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
  申请人：Van Goor Fredrick F.

  公开号：US20110098311A1

  公开（公告）日：2011-04-28

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及包含上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Pharmaceutical compositions as inhibitors of dipeptidyl peptidase-IV (DPP-IV)
  申请人：Madar J. David

  公开号：US20050215784A1

  公开（公告）日：2005-09-29

  The present invention relates to compounds that inhibit dipeptidyl peptidase IV (DPP-IV) and are useful for the prevention or treatment of diabetes, especially type II diabetes, as well as hyperglycemia, Syndrome X, hyperinsulinemia, obesity, atherosclerosis, and various immunomodulatory diseases.

  本发明涉及抑制二肽基肽酶IV（DPP-IV）的化合物，用于预防或治疗糖尿病，特别是II型糖尿病，以及高血糖、X综合征、高胰岛素血症、肥胖、动脉粥样硬化和各种免疫调节性疾病。
• [EN] INHIBITORS OF NOROVIRUS AND CORONAVIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DE NOROVIRUS ET DE CORONAVIRUS
  申请人：COCRYSTAL PHARMA INC

  公开号：WO2021206876A1

  公开（公告）日：2021-10-14

  Compounds of Formula (I) and methods of inhibiting the replication of viruses in a biological sample or patient, of reducing the amount of viruses in a biological sample or patient, and of treating a virus infection in a patient, comprising administering to said biological sample or patient an effective amount of a compound represented by Formula (I), a compound of Table A or B or a pharmaceutically acceptable salt thereof.

  公式（I）化合物及抑制生物样本或患者中病毒复制、减少生物样本或患者中病毒数量、以及治疗患者病毒感染的方法，包括向所述生物样本或患者投与由公式（I）表示的化合物、表A或B中的化合物或其药用可接受盐的有效量。