(2S)-2-<(3R)-3-<(tert-butoxycarbonyl)amino>-2-oxopyrrolidin-1-yl>-4-methylpentanoic acid | 82611-48-1

• 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
• 英文名称: (2S)-2-<(3R)-3-<(tert-butoxycarbonyl)amino>-2-oxopyrrolidin-1-yl>-4-methylpentanoic acid
• 英文别名: (R)-2-<3-<(tert-butoxycarbonyl)amino>-2-oxo-1-pyrrolidinyl>-(S)-4-methylpentanoic acid；(R)-2-{3-[(tert-butoxycarbonyl)amino]-2-oxo-1-pyrrolidinyl}-(S)-4-methylpentanoic acid；(S)-2-((R)-3-((tert-Butoxycarbonyl)amino)-2-oxopyrrolidin-1-yl)-4-methylpentanoic acid；(2S)-4-methyl-2-[(3R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxopyrrolidin-1-yl]pentanoic acid
• CAS: 82611-48-1
• 化学式: C₁₅H₂₆N₂O₅
• 分子量: 314.382
• InChiKey: JREAFDMYUYIYLC-MNOVXSKESA-N

物化性质

• 沸点：
  506.9±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-freidinger’s lactam
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: Boc-freidinger’s lactam
CAS number: 82611-48-1

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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.
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: C15H26N2O5
Molecular weight: 314.4

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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：

  (2S)-2-<(3R)-3-<(tert-butoxycarbonyl)amino>-2-oxopyrrolidin-1-yl>-4-methylpentanoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 L-lysyl-L-α-aspartyl-L-seryl-L-phenylalanyl-L-valyl-(αS,3R)-3-amino-α-(2-methylpropyl)-2-oxo-1-pyrrolidineacetyl-L-methioninamide
  参考文献：
  名称：

  Conformationally constrained tachykinin analogs: potent and highly selective neurokinin NK-2 receptor agonists

  摘要：

  The design and synthesis of potent and seleCtive neurokinin NK-2 receptor agonists 12 (GR64349) and 31 are described, together with structure-activity relationships for related analogues. Compound 12 (EC50 = 3.7 nM at NK-2 receptors in the rat colon; selectivity > 1000- and > 300-fold with respect to NK-1 and NK-3 receptors. respectively) was derived by incorporation of a Gly-Leu gamma-lactam conformational constraint into the C-terminal region of the neurokinin A. octapeptide analogue [Lys3]-NKA(3-10). Compound 31 (EC50 = 15 nM in rat colon) contains a novel fused-bicyclic constraint at the corresponding site in the substance P hexapeptide analogue [Ava6]-SP(6-11).

  DOI：

  10.1021/jm00100a027
• 作为产物：
  描述：

  在 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2S)-2-<(3R)-3-<(tert-butoxycarbonyl)amino>-2-oxopyrrolidin-1-yl>-4-methylpentanoic acid
  参考文献：
  名称：

  Cyclic peptides as selective tachykinin antagonists

  摘要：

  Twenty homodetic cyclic peptides based on the C-terminal sequence of substance P were prepared (Table I) by a combination of solid-phase techniques and cyclizations using azide coupling Incorporation of dipeptide mimics based on substituted gamma-lactams were used in some cases to restrict their conformational mobility. Five of these cyclic peptides were shown to have high tachykinin antagonist activity (pA2 > 6) at NK-2 receptors (rat vas deferens). The two most potent of this series, XVII, cyclo(Gln-Trp-Phe-Gly-Leu-Met) (pA2 = 8.1), and I cyclo(Gln-Trp-Phe-(R)Gly[ANC-2]Leu-Met) (pA2 = 6.7), were selective for NK-2 receptors compared with the other tachykinin receptors (Table II).

  DOI：

  10.1021/jm00053a001

文献信息

• Inhibitors of caspases
  申请人：Wannamaker Marion W.

  公开号：US20090048226A1

  公开（公告）日：2009-02-19

  The present invention relates to novel classes of compounds which are caspase inhibitors, in particular interleukin-1β converting enzyme (“ICE”) inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting caspase activity and consequently, may be advantageously used as agents against interleukin-1-(“IL-1”), apoptosis-, interferon-γ inducing factor-(IGIF), or interferon-γ-(“IFN-γ”) mediated diseases, including inflammatory diseases, autoimmune diseases, destructive bone disorders, proliferative disorders, infectious diseases, and degenerative diseases. This invention also relates to methods for inhibiting caspase activity and decreasing IGIF production and IFN-γ production and methods for treating interleukin-1, apoptosis-, and interferon-γ-mediated diseases using the compounds and compositions of this invention. This invention also relates to methods of preparing the compounds of this invention.

  本发明涉及一类新型化合物，它们是caspase抑制剂，特别是白细胞介素-1β转化酶（“ICE”）抑制剂。本发明还涉及包含这些化合物的药物组合物。本发明的化合物和药物组合物特别适用于抑制caspase活性，并因此可以作为对白细胞介素-1（“IL-1”）、凋亡、干扰素-γ诱导因子（IGIF）或干扰素-γ（“IFN-γ”）介导的疾病，包括炎症性疾病、自身免疫性疾病、破坏性骨疾病、增生性疾病、传染性疾病和退行性疾病的药剂。本发明还涉及抑制caspase活性、减少IGIF生成和IFN-γ生成的方法以及使用本发明的化合物和组合物治疗白细胞介素-1、凋亡和干扰素-γ介导的疾病的方法。本发明还涉及制备本发明化合物的方法。
• VEBER, DANIEL F.;FREIDINGER, ROGER
  作者：VEBER, DANIEL F.、FREIDINGER, ROGER

  DOI：——

  日期：——
• US7358273B2
  申请人：——

  公开号：US7358273B2

  公开（公告）日：2008-04-15
• Conformationally constrained tachykinin analogs: potent and highly selective neurokinin NK-2 receptor agonists
  作者：Martyn J. Deal、Russell M. Hagan、Simon J. Ireland、Christopher C. Jordan、Andrew B. McElroy、Barry Porter、Barry C. Ross、Michaela Stephens-Smith、Peter Ward

  DOI：10.1021/jm00100a027

  日期：1992.10

  The design and synthesis of potent and seleCtive neurokinin NK-2 receptor agonists 12 (GR64349) and 31 are described, together with structure-activity relationships for related analogues. Compound 12 (EC50 = 3.7 nM at NK-2 receptors in the rat colon; selectivity > 1000- and > 300-fold with respect to NK-1 and NK-3 receptors. respectively) was derived by incorporation of a Gly-Leu gamma-lactam conformational constraint into the C-terminal region of the neurokinin A. octapeptide analogue [Lys3]-NKA(3-10). Compound 31 (EC50 = 15 nM in rat colon) contains a novel fused-bicyclic constraint at the corresponding site in the substance P hexapeptide analogue [Ava6]-SP(6-11).
• Cyclic peptides as selective tachykinin antagonists
  作者：Brian J. Williams、Neil R. Curtis、Alexander T. McKnight、Janet J. Maguire、Stephen C. Young、Daniel F. Veber、Raymond Baker

  DOI：10.1021/jm00053a001

  日期：1993.1

  Twenty homodetic cyclic peptides based on the C-terminal sequence of substance P were prepared (Table I) by a combination of solid-phase techniques and cyclizations using azide coupling Incorporation of dipeptide mimics based on substituted gamma-lactams were used in some cases to restrict their conformational mobility. Five of these cyclic peptides were shown to have high tachykinin antagonist activity (pA2 > 6) at NK-2 receptors (rat vas deferens). The two most potent of this series, XVII, cyclo(Gln-Trp-Phe-Gly-Leu-Met) (pA2 = 8.1), and I cyclo(Gln-Trp-Phe-(R)Gly[ANC-2]Leu-Met) (pA2 = 6.7), were selective for NK-2 receptors compared with the other tachykinin receptors (Table II).