1-(2-羟基苯基)-5-氧代吡咯烷-3-羧酸 | 39629-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(2-羟基苯基)-5-氧代吡咯烷-3-羧酸
• 中文别名: 1-(2-羟基苯基)-5-氧吡咯烷-3-羧酸
• 英文名称: 1-(2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid
• 英文别名: 1-(2-Hydroxy-phenyl)-5-oxo-pyrrolidin-3-carbonsaeure
• CAS: 39629-89-5
• 化学式: C₁₁H₁₁NO₄
• mdl: MFCD00683917
• 分子量: 221.213
• InChiKey: FPQOSKXLHCTVED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933790090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(2-Hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid
Synonyms: 1-(2-Hydroxyphenyl)-2-pyrrolidinone-4-carboxylic acid

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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-(2-Hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid
CAS number: 39629-89-5

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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.
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: C11H11NO4
Molecular weight: 221.2

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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-(2-羟基苯基)-5-氧代吡咯烷-3-羧酸 在 盐酸 、 hydrazine hydrate 、 硫酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 7.0h， 生成 1-(2-hydroxyphenyl)-4-(3,5-dimethyl-1H-pyrazol-1-carbonyl)pyrrolidin-2-one
  参考文献：
  名称：

  1-(2-Hydroxyphenyl)- 和 (3,5-Dichloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid 衍生物的合成作为开发新型抗菌和抗癌药物的有前途的支架

  摘要：

  革兰氏阳性病原体和致病真菌之间不断增加的抗菌素耐药性仍然是主要的公共卫生威胁之一。因此，迫切需要新型抗菌候选物和支架来克服革兰氏阳性病原体和耐药真菌病原体的耐药性。在这项研究中，我们探索了 1-(2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid 及其 3,5-dichloro-2-hydroxyphenyl 类似物对多重耐药病原体的体外抗菌活性。这些化合物对革兰氏阳性病原体（金黄色葡萄球菌、粪肠球菌、艰难梭菌）显示出结构依赖性抗菌活性。化合物 14 和 24b 对万古霉素中间体金黄色葡萄球菌菌株显示出有希望的活性，并且在 HSAEC-1 细胞中具有良好的细胞毒性特征，使它们成为有吸引力的支架以供进一步开发。发现具有 3,5-二氯-2-羟基苯基取代基的 5-氟苯并咪唑是四倍的，而具有噻吩-2-基片段的腙对耐甲氧西林金黄色葡萄球菌的作用是克林霉素的两倍TCH

  DOI：

  10.3390/ijms24097966
• 作为产物：
  描述：

  衣康酸 、 2-氨基苯酚 以 水 为溶剂， 以74.4 %的产率得到1-(2-羟基苯基)-5-氧代吡咯烷-3-羧酸
  参考文献：
  名称：

  1-(2-Hydroxyphenyl)- 和 (3,5-Dichloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid 衍生物的合成作为开发新型抗菌和抗癌药物的有前途的支架

  摘要：

  革兰氏阳性病原体和致病真菌之间不断增加的抗菌素耐药性仍然是主要的公共卫生威胁之一。因此，迫切需要新型抗菌候选物和支架来克服革兰氏阳性病原体和耐药真菌病原体的耐药性。在这项研究中，我们探索了 1-(2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid 及其 3,5-dichloro-2-hydroxyphenyl 类似物对多重耐药病原体的体外抗菌活性。这些化合物对革兰氏阳性病原体（金黄色葡萄球菌、粪肠球菌、艰难梭菌）显示出结构依赖性抗菌活性。化合物 14 和 24b 对万古霉素中间体金黄色葡萄球菌菌株显示出有希望的活性，并且在 HSAEC-1 细胞中具有良好的细胞毒性特征，使它们成为有吸引力的支架以供进一步开发。发现具有 3,5-二氯-2-羟基苯基取代基的 5-氟苯并咪唑是四倍的，而具有噻吩-2-基片段的腙对耐甲氧西林金黄色葡萄球菌的作用是克林霉素的两倍TCH

  DOI：

  10.3390/ijms24097966

文献信息

• Synthesis of a novel and potent small-molecule antagonist of PAC1 receptor for the treatment of neuropathic pain
  作者：Ichiro Takasaki、Haruna Ogashi、Takuya Okada、Ayaka Shimodaira、Daichi Hayakawa、Ai Watanabe、Atsuro Miyata、Takashi Kurihara、Hiroaki Gouda、Naoki Toyooka

  DOI：10.1016/j.ejmech.2019.111902

  日期：2020.1

  identified novel small-molecule antagonists of the PACAP type I (PAC1) receptor using docking-based in silico screening followed by in vitro/vivo pharmacological assays. In the present study, we synthesized 18 novel derivatives based on the structure of PA-9, a recently developed antagonist of the PAC1 receptor, with a view to obtain a panel of compounds with more potent antagonistic and analgesic activities

  我们最近使用基于对接的计算机模拟筛选，然后进行体外/体内药理学鉴定，确定了PACAP I型（PAC1）受体的新型小分子拮抗剂。在本研究中，我们基于PA-9（一种最近开发的PAC1受体拮抗剂）的结构合成了18种新型衍生物，以期获得一组具有更强的拮抗和镇痛活性的化合物。其中，化合物3d显示出改善的拮抗活性。鞘内注射3d抑制垂体腺苷酸环化酶激活多肽（PACAP）和脊髓神经结扎诱导的机械性异常性疼痛。效果比PA-9更有效。口服给药后，化合物3d也显示出抗痛觉过敏作用。因此，
• ANALGESIC DRUG USING PAC1 RECEPTOR ANTAGONISTIC DRUG
  申请人：KAGOSHIMA UNIVERSITY

  公开号：US20210188841A1

  公开（公告）日：2021-06-24

  This invention relates to an analgesic drug comprising a compound represented by the following formula (I) or (II), wherein R 1 is a C 1-6 -alkoxy group or a C 1-6 -haloalkoxy group; R 2 is a hydrogen atom; and R is an indazolyl group substituted with a halogen atom; a substituted or unsubstituted phenyl group; a pyrazolyl group; or a substituted or unsubstituted aralkyl group; or a salt thereof, or a solvate thereof.

  本发明涉及一种镇痛药物，包含下式（I）或（II）所表示的化合物，其中R1为C1-6-烷氧基或C1-6-卤代烷氧基；R2为氢原子；R为取代有卤素原子的吲唑基；取代或未取代的苯基；吡唑基；或取代或未取代的芳基烷基；或其盐或溶剂化物。
• 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
• Synthesis of 1-(2-Hydroxyphenyl)- and (3,5-Dichloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid Derivatives as Promising Scaffolds for the Development of Novel Antimicrobial and Anticancer Agents
  作者：Monika Bertašiūtė、Povilas Kavaliauskas、Rita Vaickelionienė、Birutė Grybaitė、Vidmantas Petraitis、Rūta Petraitienė、Ethan Naing、Andrew Garcia、Jūratė Šiugždaitė、Raimundas Lelešius、Vytautas Mickevičius

  DOI：10.3390/ijms24097966

  日期：——

  activity characterization demonstrated that the 5-fluorobenzimidazole derivative with a 3,5-dichloro-2-hydroxyphenyl substituent showed the highest anticancer activity in an A549 human pulmonary cancer cell culture model. Collectively these results demonstrate that 1-(2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives could be further explored for the development of novel candidates targeting

  革兰氏阳性病原体和致病真菌之间不断增加的抗菌素耐药性仍然是主要的公共卫生威胁之一。因此，迫切需要新型抗菌候选物和支架来克服革兰氏阳性病原体和耐药真菌病原体的耐药性。在这项研究中，我们探索了 1-(2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid 及其 3,5-dichloro-2-hydroxyphenyl 类似物对多重耐药病原体的体外抗菌活性。这些化合物对革兰氏阳性病原体（金黄色葡萄球菌、粪肠球菌、艰难梭菌）显示出结构依赖性抗菌活性。化合物 14 和 24b 对万古霉素中间体金黄色葡萄球菌菌株显示出有希望的活性，并且在 HSAEC-1 细胞中具有良好的细胞毒性特征，使它们成为有吸引力的支架以供进一步开发。发现具有 3,5-二氯-2-羟基苯基取代基的 5-氟苯并咪唑是四倍的，而具有噻吩-2-基片段的腙对耐甲氧西林金黄色葡萄球菌的作用是克林霉素的两倍TCH