1-Cbz-哌啶-2-甲酰胺 | 940868-17-7

• 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: 1-Cbz-哌啶-2-甲酰胺
• 中文别名: 1-CBZ-哌啶-2-甲酰胺；1-苄氧羰基哌啶-2-甲酰胺
• 英文名称: benzyl 2-(aminocarbonyl)piperidine-1-carboxylate
• 英文别名: Benzyloxycarbonyl-D-pipecolic acid amide；Benzyl 2-carbamoylpiperidine-1-carboxylate
• CAS: 940868-17-7
• 化学式: C₁₄H₁₈N₂O₃
• mdl: MFCD09878798
• 分子量: 262.309
• InChiKey: AJMWIWWTWGDVSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Benzyl 2-carbamoylpiperidine-1-carboxylate
Synonyms: 1-CBZ-Pipecolinamide

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: Benzyl 2-carbamoylpiperidine-1-carboxylate
CAS number: 940868-17-7

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C14H18N2O3
Molecular weight: 262.3

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-Cbz-哌啶-2-甲酰胺 在 palladium on activated charcoal 盐酸羟胺 、 氢气 、 三乙胺 、 三氟乙酸酐 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 8.0h， 生成 N-(4-fluorobenzyl)-5,6-dihydroxy-2-piperidin-2-ylpyrimidine-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：

  六氢吡啶-alpha-羧酸 在 氨 、 sodium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 1-Cbz-哌啶-2-甲酰胺
  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

文献信息

• Discovery and Synthesis of HIV Integrase Inhibitors:  Development of Potent and Orally Bioavailable N-Methyl Pyrimidones
  作者：Cristina Gardelli、Emanuela Nizi、Ester Muraglia、Benedetta Crescenzi、Marco Ferrara、Federica Orvieto、Paola Pace、Giovanna Pescatore、Marco Poma、Maria del Rosario Rico Ferreira、Rita Scarpelli、Carl F. Homnick、Norihiro Ikemoto、Anna Alfieri、Maria Verdirame、Fabio Bonelli、Odalys Gonzalez Paz、Marina Taliani、Edith Monteagudo、Silvia Pesci、Ralph Laufer、Peter Felock、Kara A. Stillmock、Daria Hazuda、Michael Rowley、Vincenzo Summa

  DOI：10.1021/jm0704705

  日期：2007.10.1

  reverse transcriptase, a protease, and an integrase. The latter is responsible for the integration of the viral genome into the human genome and, therefore, represents an attractive target for chemotherapeutic intervention against AIDS. A drug based on this mechanism has not yet been approved. Benzyl-dihydroxypyrimidine-carboxamides were discovered in our laboratories as a novel and metabolically stable

  人类1型免疫缺陷病毒（HIV-1）编码三种对于病毒复制必不可少的酶：逆转录酶，蛋白酶和整合酶。后者负责将病毒基因组整合到人类基因组中，因此代表了对AIDS进行化学疗法干预的诱人靶标。基于这种机制的药物尚未获得批准。在我们的实验室中发现苄基-二羟基嘧啶-羧酰胺是一类新型的，代谢稳定的药物，对HIV整合酶链转移步骤具有有效的抑制作用。进一步的努力导致了基于结构相关的N-Me嘧啶酮骨架的非常有效的化合物。该系列中最有趣的化合物之一是2-N-Me-吗啉代衍生物27a，其显示在血清存在下细胞中的CIC95为65 nM。该化合物在三种临床前物种中均具有良好的药代动力学特性，并且在几种抗筛选试验中未显示任何责任。
• Tripeptides acting on the central nervous system and a process for the
  申请人：Richter Gedeon Vegyeszeti Gyar Rt.

  公开号：US04299821A1

  公开（公告）日：1981-11-10

  The invention relates to new peptide derivatives which act on the central nervous system and correspond to the general formula (I), Glp--X--Y--NH--A (I) wherein X is L-norleucyl, L-leucyl, L-norvalyl, D-leucyl, L-prolyl, L-2-aminobutyryl, L-valyl, L-threonyl, L-isoleucyl, L-2-aminodecanoyl, L-cyclohexylalanyl or L-tert.-butyl-seryl group and Y is L-prolyl group, or X is L-histidyl group and Y is L-homoprolyl or D-pipecolyl group, furthermore A is hydrogen, a C.sub.1-10 alkyl group or a C.sub.1-3 alkyl group having a dimethylamino substituent, with the proviso that if X is L-leucyl group, A is other than hydrogen, and pharmaceutically acceptable complexes thereof. These compounds are prepared by methods commonly applied in the peptide chemistry.

  该发明涉及一种作用于中枢神经系统的新肽衍生物，其对应于一般式（I），Glp--X--Y--NH--A（I），其中X为L-诺亮氨酰基、L-亮氨酰基、L-诺缬氨酰基、D-亮氨酰基、L-脯氨酰基、L-2-氨基丁酰基、L-缬氨酰基、L-苏氨酰基、L-异亮氨酰基、L-2-氨基癸酰基、L-环己基丙氨酰基或L-叔丁基丝氨酰基，Y为L-脯氨酰基，或者X为L-组氨酰基，Y为L-同脯氨酰基或D-哌哪酰基，此外A为氢、C.sub.1-10烷基或具有二甲胺取代基的C.sub.1-3烷基，但若X为L-亮氨酰基，则A不是氢，并且其药用上可接受的配合物。这些化合物通过常用的肽化学方法制备。
• US4299821A
  申请人：——

  公开号：US4299821A

  公开（公告）日：1981-11-10
• Dihydroxypyrimidine-4-carboxamides as Novel Potent and Selective HIV Integrase Inhibitors
  作者：Paola Pace、M. Emilia Di Francesco、Cristina Gardelli、Steven Harper、Ester Muraglia、Emanuela Nizi、Federica Orvieto、Alessia Petrocchi、Marco Poma、Michael Rowley、Rita Scarpelli、Ralph Laufer、Odalys Gonzalez Paz、Edith Monteagudo、Fabio Bonelli、Daria Hazuda、Kara A. Stillmock、Vincenzo Summa

  DOI：10.1021/jm070027u

  日期：2007.5.1

  chemotherapeutic intervention in the treatment of AIDS that has also recently been confirmed in the clinical setting. We report here on the design and synthesis of N-benzyl-5,6-dihydroxypyrimidine-4-carboxamides as a class of agents which exhibits potent inhibition of the HIV-integrase-catalyzed strand transfer process. In the current study, structural modifications on these molecules were made in order

  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。