Cbz-环亮氨酸 | 17191-44-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: Cbz-环亮氨酸
• 中文别名: 1-(Cbz-氨基)环戊甲酸；N-苄氧羰基-1-氨基-1-环戊烷甲酸
• 英文名称: 1-{[(benzyloxy)carbonyl]amino}cyclopentanecarboxylic acid
• 英文别名: N-benzyloxycarbonyl-1-aminocyclopentane-1-carboxylic acid；Cbz-Cycloleucine；1-(phenylmethoxycarbonylamino)cyclopentane-1-carboxylic acid
• CAS: 17191-44-5
• 化学式: C₁₄H₁₇NO₄
• mdl: MFCD02094399
• 分子量: 263.293
• InChiKey: IXXMJXGMYKDTRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  95-98 °C
• 沸点：
  468.2±34.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：室温、密封、干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Cbz-1-amino-1-cyclopentanecarboxylic acid
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: Cbz-1-amino-1-cyclopentanecarboxylic acid
CAS number: 17191-44-5

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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: C14H17NO4
Molecular weight: 263.3

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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

反应信息

• 作为反应物：
  描述：

  Cbz-环亮氨酸 在 palladium on activated charcoal 吡啶 、 二碳酸二叔丁酯 、 氢气 、 羟胺 、 碳酸氢铵 、 三乙胺 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 、 xylene 为溶剂， 反应 31.5h， 生成 2-(1-aminocyclopentyl)-N-[(4-fluorophenyl)methyl]-5-hydroxy-6-oxo-1H-pyrimidine-4-carboxamide
  参考文献：
  名称：

  Dihydroxypyrimidine-4-carboxamides作为新型有效和选择性的HIV整合酶抑制剂。

  摘要：

  人类免疫缺陷病毒1型（HIV-1）整合酶是复制所需的三种组成型病毒酶之一，是化学疗法干预AIDS的合理靶标，最近在临床环境中也得到了证实。我们在这里报告的N-苄基5,6-二羟基嘧啶-4-羧酰胺的设计和合成作为一类药物，对HIV整合酶催化的链转移过程具有有效的抑制作用。在当前的研究中，对这些分子进行了结构修饰，以检查其对HIV整合酶抑制效能的影响。该系列中最有趣的化合物之一是2- [1-（二甲基氨基）-1-甲基乙基] -N-（4-氟苄基）-5,6-二羟基嘧啶-4-羧酰胺38，CIC95为78 nM。在血清蛋白存在下进行基于细胞的测定。

  DOI：

  10.1021/jm070027u
• 作为产物：
  描述：

  氯甲酸苄酯 、 环亮氨酸 在 sodium hydroxide 作用下， 生成 Cbz-环亮氨酸
  参考文献：
  名称：

  多肽。第七部分 胃泌素C末端四肽酰胺序列中苯丙氨酰位置的变化

  摘要：

  描述了L-色氨酸-L-甲硫酰基-L-天冬氨酰-L-苯丙氨酸酰胺（胃泌素的C-末端序列）或其N-苄氧羰基，-叔丁氧羰基或-氨基甲酰基衍生物的类似物的合成。苯丙氨酰基残基已被其他天然存在的氨基酰基残基或αα-二取代的氨基酰基残基取代，或已通过（a）在对位取代芳环进行修饰，（b）芳环的氢化，（c）亚氨基从α-碳原子转换为β-碳原子，（d）将苯环从β-碳原子转换为α-碳原子，（e）取代β-碳原子上的羟基，或（f）亚氨基的甲基化。

  DOI：

  10.1039/j39680000531

文献信息

• Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights
  作者：Atsushi Ueda、Tomohiro Umeno、Mitsunobu Doi、Kengo Akagawa、Kazuaki Kudo、Masakazu Tanaka

  DOI：10.1021/acs.joc.6b00982

  日期：2016.8.5

  Helical peptide foldamer catalyzed Michael addition reactions of nitroalkane or dialkyl malonate to α,β-unsaturated ketones are reported along with the mechanistic considerations of the enantio-induction. A wide variety of α,β-unsaturated ketones, including β-aryl, β-alkyl enones, and cyclic enones, were found to be catalyzed by the helical peptide to give Michael adducts with high enantioselectivities

  报道了螺旋肽折叠剂催化硝基烷或丙二酸二烷基酯与α，β-不饱和酮的迈克尔加成反应，以及对映体诱导的机理考虑。发现各种α，β-不饱和酮，包括β-芳基，β-烷基烯酮和环状烯酮，都可以被螺旋肽催化，从而得到具有高对映选择性（高达99％）的迈克尔加合物。根据X射线晶体学分析和depsipeptide研究，α-螺旋肽催化剂N端的酰胺质子N（2）–H和N（3）–H对激活迈克尔供体至关重要，而N-末端伯胺通过亚胺离子中间体的形成激活了迈克尔受体。
• Chemical communication: conductors and insulators of screw-sense preference between helical oligo(aminoisobutyric acid) domains
  作者：Thomas Boddaert、Jordi Solà、Madeleine Helliwell、Jonathan Clayden

  DOI：10.1039/c2cc00060a

  日期：——

  1H NMR studies quantify the abilities of achiral amino acids to communicate a left-handed screw-sense preference from one helical Aib4 domain to another: certain quaternary amino acids (e.g. Ac6c) act as effective conductors of conformational preference while others (e.g. diphenylglycine) acts as insulators.

  1H NMR研究表明，非手性氨基酸能够传递从螺旋Aib4结构域到另一个结构域的左旋螺向偏好：某些四级氨基酸（如Ac6c）能有效传递构象偏好，而其他氨基酸（如双苯甘氨酸）则起到绝缘体的作用。
• Chlamydocin–hydroxamic acid analogues as histone deacetylase inhibitors
  作者：Norikazu Nishino、Binoy Jose、Ryuzo Shinta、Tamaki Kato、Yasuhiko Komatsu、Minoru Yoshida

  DOI：10.1016/j.bmc.2004.08.041

  日期：2004.11

  Chlamydocin-hydroxamic acid analogues were designed and synthesized as histone deacetylase (HDAC) inhibitors based on the structure and HDAC inhibitory activity of chlamydocin and trichostatin A. Chlamydocin is a cyclic tetrapeptide containing an epoxyketone moiety in the side chain that makes it an irreversible inhibitor of HDAC. We replaced the epoxyketone moiety of chlamydocin with hydroxamic acid to

  根据衣原霉素和曲古抑菌素A的结构和HDAC抑制活性，设计并合成了衣原霉素-异羟肟酸类似物作为组蛋白脱乙酰基酶（HDAC）抑制剂。衣原霉素是环状四肽，在侧链中含有环氧酮部分，使其成为不可逆抑制剂。 HDAC。我们用异羟肟酸代替了衣原体的环氧酮部分，以设计有效且可逆的HDAC抑制剂。另外，对于一系列衣藻多菌素类似物系列，引入了许多氨基-环烷羧酸（Acc）而不是简单的氨基-异丁酸（Aib）。测试了所合成的化合物的HDAC抑制活性，结果表明其中许多是HDAC的有效抑制剂。用芳香族氨基酸代替衣原体的Aib残基增强了体内和体外的抑制活性。我们已经对衣原霉素-异羟肟酸类似物进行了圆二色性和分子模拟研究，并将其与衣原霉素的溶液结构进行了比较。
• Helical foldamer-catalyzed enantioselective 1,4-addition reaction of dialkyl malonates to cyclic enones
  作者：Tomohiro Umeno、Atsushi Ueda、Mitsunobu Doi、Takuma Kato、Makoto Oba、Masakazu Tanaka

  DOI：10.1016/j.tetlet.2019.151301

  日期：2019.12

  -amino acid into L-Leu-based heptapeptides preferentially induced right-handed (P) helical structures. Using 5∼20 mol % of a single helical foldamers-catalyst, enantioselective 1,4-addition reactions of dialkyl malonates to cycloalk-2-enones (5∼7 rings) proceeded to give chiral 3-substituted cycloalkanones with 94∼99% ee in moderate chemical yields, regardless of the ring size of substrates.

  将五元环的α，α-二取代的α-氨基酸引入L-Leu基七肽中，优先诱导右旋（P）螺旋结构。用5〜20mol％的单一螺旋形折叠催化剂，丙二酸二烷基酯与环烷-2-烯酮（5〜7个环）的对映选择性1，4-加成反应进行，得到ee为94〜99％的手性3-取代的环烷酮。不论底物的环大小如何，化学产率均中等。
• [EN] BICYCLIC COMPOUNDS AND METHODS FOR THEIR USE IN TREATING PITT HOPKINS SYNDROME<br/>[FR] COMPOSÉS BICYCLIQUES ET PROCÉDÉS DESTINÉS À LEUR UTILISATION DANS LE TRAITEMENT DU SYNDROME DE PITT HOPKINS
  申请人：NEUREN PHARMACEUTICALS LTD

  公开号：WO2021080646A1

  公开（公告）日：2021-04-29

  Embodiments of this invention provide compounds, compositions, methods, and uses for therapeutic diketopiperazines, including cyclic G-2-Allyl Proline and other cyclic Glycyl Proline compounds to treat Pitt Hopkins Syndrome and symptoms thereof, as well as manufacture of compositions, medicaments including tablets, capsules, liquid formulations, gels, injectable solutions, and other formulations that are useful for treatment of such conditions.

  该发明的实施例提供了治疗二酮哌啶类化合物、组合物、方法和用途，包括环状G-2-丙烯基脯氨酸和其他环状甘氨酰脯氨酸化合物，用于治疗皮特-霍普金斯综合征及其症状，以及制备包括片剂、胶囊、液体配方、凝胶、注射溶液和其他适用于治疗此类疾病的组合物、药物。