1-萘-1-基-5-氧代-吡咯烷-3-羧酸 | 340319-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-萘-1-基-5-氧代-吡咯烷-3-羧酸
• 英文名称: 1-[1]naphthyl-5-oxo-pyrrolidine-3-carboxylic acid
• 英文别名: 1-[1]Naphthyl-5-oxo-pyrrolidin-3-carbonsaeure；1-(Naphthalen-1-yl)-5-oxopyrrolidine-3-carboxylic acid；1-naphthalen-1-yl-5-oxopyrrolidine-3-carboxylic acid
• CAS: 340319-91-7
• 化学式: C₁₅H₁₃NO₃
• mdl: MFCD02197525
• 分子量: 255.273
• InChiKey: XARHILSRKCHUAE-UHFFFAOYSA-N

物化性质

• 熔点：
  211 °C
• 沸点：
  580.7±43.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933790090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Naphthalen-1-yl-5-oxo-pyrrolidine-3-carboxylic 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: 1-Naphthalen-1-yl-5-oxo-pyrrolidine-3-carboxylic acid
CAS number: 340319-91-7

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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: C15H13NO3
Molecular weight: 255.3

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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：

  1-萘-1-基-5-氧代-吡咯烷-3-羧酸 在 盐酸 、 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 4-(1-Methylbenzimidazol-2-yl)-1-naphthalen-1-ylpyrrolidin-2-one
  参考文献：
  名称：

  作为 MRSA 感染特异性治疗药物的新型 SaFabI 抑制剂的发现和优化

  摘要：

  作为脂肪酸生物合成中的限速酶，金黄色葡萄球菌烯酰酰基载体蛋白还原酶 ( Sa FabI)​​ 成为对抗耐甲氧西林金黄色葡萄球菌(MRSA) 感染的引人注目的靶标。在此，以 4-(1 H-苯并[ d ]咪唑-2-基)吡咯烷-2-酮支架为特征的化合物1被内部鉴定为有效的Sa FabI 抑制剂 (IC 50 = 976.8 nM)图书馆。随后的优化产生了化合物n31 ，其对酶活性的抑制功效（IC 50 = 174.2 nM）和对金黄色葡萄球菌的选择性效力（MIC = 1–2 μg/mL）得到改善。从机制上讲， n31在细胞环境中直接抑制Sa FabI。此外， n31表现出良好的安全性和药代动力学特征，并且可以剂量依赖性地治疗 MRSA 引起的皮肤感染，其效果优于已批准的药物利奈唑胺。 n31的手性分离产生( S )-n31 ，具有优异的活性（IC 50 = 94.0 nM，MIC = 0.25–1

  DOI：

  10.1021/acs.jmedchem.4c00320
• 作为产物：
  描述：

  衣康酸 、 1-萘胺 在 水 作用下， 生成 1-萘-1-基-5-氧代-吡咯烷-3-羧酸
  参考文献：
  名称：

  Scharfenberg, Justus Liebigs Annalen der Chemie, 1889, vol. 254, p. 150

  摘要：

  DOI：

文献信息

• Scharfenberg, Justus Liebigs Annalen der Chemie, 1889, vol. 254, p. 150
  作者：Scharfenberg

  DOI：——

  日期：——
• The Reaction of Itaconic Acid with Primary Amines
  作者：Peter L. Paytash、Edward Sparrow、Joseph C. Gathe

  DOI：10.1021/ja01159a520

  日期：1950.3
• 10.1021/acs.jmedchem.4c00320
  作者：Zhang, Laiying、Yang, Jiaxing、Xu, Xin、Zhang, Jiangnan、Qiu, Zhiqiang、Ju, Yuan、Luo, Baozhu、Liu, Yan、Gou, Xupeng、Sui, Jing、Chen, Baoyi、Wang, Yanmei、Tao, Tao、He, Lei、Yang, Tao、Luo, Youfu

  DOI：10.1021/acs.jmedchem.4c00320

  日期：——

  Staphylococcus aureus enoyl-acyl carrier protein reductase (SaFabI) emerges as a compelling target for combating methicillin-resistant S. aureus (MRSA) infections. Herein, compound 1, featuring a 4-(1H-benzo[d]imidazol-2-yl)pyrrolidin-2-one scaffold, was identified as a potent SaFabI inhibitor (IC50 = 976.8 nM) from an in-house library. Subsequent optimization yielded compound n31, with improved inhibitory efficacy

  作为脂肪酸生物合成中的限速酶，金黄色葡萄球菌烯酰酰基载体蛋白还原酶 ( Sa FabI)​​ 成为对抗耐甲氧西林金黄色葡萄球菌(MRSA) 感染的引人注目的靶标。在此，以 4-(1 H-苯并[ d ]咪唑-2-基)吡咯烷-2-酮支架为特征的化合物1被内部鉴定为有效的Sa FabI 抑制剂 (IC 50 = 976.8 nM)图书馆。随后的优化产生了化合物n31 ，其对酶活性的抑制功效（IC 50 = 174.2 nM）和对金黄色葡萄球菌的选择性效力（MIC = 1–2 μg/mL）得到改善。从机制上讲， n31在细胞环境中直接抑制Sa FabI。此外， n31表现出良好的安全性和药代动力学特征，并且可以剂量依赖性地治疗 MRSA 引起的皮肤感染，其效果优于已批准的药物利奈唑胺。 n31的手性分离产生( S )-n31 ，具有优异的活性（IC 50 = 94.0 nM，MIC = 0.25–1