3-(3-氧代-3,4-二氢-2-喹噁啉)-丙酸 | 7712-28-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-(3-氧代-3,4-二氢-2-喹噁啉)-丙酸
• 中文别名: 3-(3-羟基喹唑啉-2-基)丙酸
• 英文名称: 3-(3-oxo-3,4-dihydroquinoxalin-2-yl)propanoic acid
• 英文别名: β-(3-Oxy-2-chinoxalyl)-propionsaeure；3-(3-hydroxyquinoxalin-2-yl)propanoic acid
• CAS: 7712-28-9
• 化学式: C₁₁H₁₀N₂O₃
• mdl: MFCD01820403
• 分子量: 218.212
• InChiKey: HROJWOXFEZYMGL-UHFFFAOYSA-N

物化性质

• 熔点：
  262-262.5 °C
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  78.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  储存条件：2-8℃，请密封保存并确保环境干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(3-Hydroxyquinoxalin-2-yl)propanoic 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: 3-(3-Hydroxyquinoxalin-2-yl)propanoic acid
CAS number: 7712-28-9

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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: C11H10N2O3
Molecular weight: 218.2

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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：

  3-(3-氧代-3,4-二氢-2-喹噁啉)-丙酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 4.0h， 以82%的产率得到3,4-dihydro-2H-pyrano[2,3-b]quinoxalin-2-one
  参考文献：
  名称：

  新的喹喔啉衍生物作为凋亡诱导剂和EGFR抑制剂的设计，合成，抗增殖评价和分子对接研究

  摘要：

  合成了一系列新的喹喔啉衍生物，并针对（HepG-2，HCT-116和MCF-7）细胞系进行了药理学评估。发现七种化合物对所检查的细胞系具有最高活性，IC 50值在（7.57至28.44 µM）之间。为了进一步分析其在MCF-7细胞中的凋亡潜力，最活跃的3a，3b，6、7b，7c，7d和7f成员已被选择。有趣的是，它发现Bcl-2水平相对于对照降低了1.95–3.99倍，BAX水平升高了7.2-10.6倍。与未处理的细胞相比，它们还将活性Caspase-3水平提高了5.77-10.69倍。用这些化合物处理WI38细胞，以估计这些化合物在非致瘤细胞中的细胞毒性水平，它们显示出更高的IC 50值（142.21-335.03μM），表明对正常细胞的毒性作用可能较小。对最有前途的化合物3a，6、7b和7d机理的进一步研究表明，它增加了凋亡细胞，并诱导了前G1和G2 / M期的细胞周期停滞。此外，野生EGFR

  DOI：

  10.1016/j.molstruc.2021.130317
• 作为产物：
  描述：

  methyl 3-(3-oxo-3,4-dihydroquinoxalin-2-yl)propanoate 在 盐酸 、 lithium hydroxide 作用下， 以 N-甲基乙酰胺 、 水 、 二甲基亚砜 为溶剂， 以97%的产率得到3-(3-氧代-3,4-二氢-2-喹噁啉)-丙酸
  参考文献：
  名称：

  Triazolo and derivatives as chemokine inhibitors

  摘要：

  由以下公式表示的新颖三唑衍生物及其药用盐，以及含有相同物质作为有效成分的趋化因子抑制剂。这些对于过敏疾病如支气管哮喘和特应性皮炎的治疗剂、慢性类风湿性关节炎等炎症性疾病的治疗剂、溃疡性结肠炎和肾炎等自身免疫疾病的治疗剂以及抗艾滋病药物都是有用的。

  公开号：

  US06492364B1

文献信息

• 具有基质金属蛋白酶抑制活性的喹喔啉衍生 物及其制备方法和应用
  申请人：山东大学

  公开号：CN108997230B

  公开（公告）日：2020-08-04

  本发明公开了具有基质金属蛋白酶抑制活性的喹喔啉衍生物及其制备方法和应用，本发明合成了一系列具有特异性基质金属蛋白酶‑9和/或基质金属蛋白酶‑13抑制活性的喹喔啉衍生物，该类化合物可作为MMP‑9和/或基质金属蛋白酶‑13特异性抑制剂，进而可成为治疗指数较高的可用于临床的药物，解决了现有技术中治疗骨关节炎、骨质疏松、牙周病药物种类较少、疗效不够确切等问题。
• Nitrogen-containing heterocyclic compound and use thereof
  申请人：Ikeura Yoshinori

  公开号：US20090156572A1

  公开（公告）日：2009-06-18

  The present invention relates to a compound represented by the formula wherein ring A is a nitrogen-containing heterocycle optionally further having substituent(s), ring B is an aromatic ring optionally having substituent(s), ring C is a cyclic group optionally having substituent(s), R 1 is a hydrogen atom, a hydrocarbon group optionally having substituent(s), an acyl group, a heterocyclic group optionally having substituent(s) or an amino group optionally having substituent(s), R 2 is an optionally halogenated C 1-6 alkyl group, m and n are each an integer of 0 to 5, m+n is an integer of 2 to 5, and is a single bond or a double bond, or a salt thereof and the like. Since the compound has a superior tachykinin receptor antagonistic action, and is useful as an agent for the prophylaxis or treatment of various diseases such as lower urinary tract diseases, gastrointestinal diseases, central nervous system diseases and the like.

  本发明涉及一种由下式表示的化合物：其中环A是含氮杂环，可选择地进一步具有取代基，环B是芳香环，可选择地具有取代基，环C是环状基团，可选择地具有取代基，R1是氢原子，一个碳氢基团，可选择地具有取代基，酰基，一个杂环基团，可选择地具有取代基或一个氨基团，可选择地具有取代基，R2是可选择卤代的C1-6烷基基团，m和n分别是0到5的整数，m+n是2到5的整数，是单键或双键，或其盐等。由于该化合物具有优越的催吐肽受体拮抗作用，可用作预防或治疗多种疾病的药物，如下尿道疾病、胃肠道疾病、中枢神经系统疾病等。
• Evaluation of quinoxaline compounds as ligands of a site adjacent to S2 (AS2) of cruzain
  作者：Lucas Fabian、M. Florencia Martini、Emir Salas Sarduy、Darío A. Estrin、Albertina G. Moglioni

  DOI：10.1016/j.bmcl.2019.06.046

  日期：2019.8

  The binding of ten quinoxaline compounds (1–10) to a site adjacent to S2 (AS2) of cruzain (CRZ) was evaluated by a protocol that include a first analysis through docking experiments followed by a second analysis using the Molecular Mechanics-Poisson-Boltzmann Surface Area method (MM-PBSA). Through them we demonstrated that quinoxaline compounds bearing substituents of different sizes at positions 3

  10喹喔啉化合物（结合1 - 10）到邻近的cruzain S2（AS2）（CRZ）的位点是由包括通过使用分子对接实验之后的第二分析力学-泊松第一分析的协议评价玻尔兹曼表面积法（MM-PBSA）。通过它们，我们证明了在杂环的3位或4位带有不同大小取代基的喹喔啉化合物可能与AS2相互作用，这是药物设计中特别有趣的部位。这些化合物的对接分数（ΔGdock）与通过非共价相互作用与酶结合的抑制剂估计的对接分数相似。但是，MM-PBSA估计的自由结合能（ΔG）值表明，衍生物8在动态研究中，– 10在杂环的3位带有大的取代基，并从结合位点脱离。出乎意料的是，对某些衍生物的克鲁普西汀（CZ）抑制活性的评估表明，它们增加了酶促活性。这些结果使我们得出结论，即AS2作为化合物结合位点的口袋的相关性，但不一定用于抗chagasic化合物的设计。
• Design, synthesis and biological evaluation of quinoxaline compounds as anti-HIV agents targeting reverse transcriptase enzyme
  作者：Lucas Fabian、Marisa Taverna Porro、Natalia Gómez、Melina Salvatori、Gabriela Turk、Darío Estrin、Albertina Moglioni

  DOI：10.1016/j.ejmech.2019.111987

  日期：2020.2

  mutations. Quinoxaline derivatives are an emergent class of heterocyclic compounds with a wide spectrum of biological activities and therapeutic applications. These types of compounds have also shown high potency in the inhibition of HIV reverse transcriptase and HIV replication in cell culture. For these reasons we propose, in this work, the design, synthesis and biological evaluation of quinoxaline derivatives

  人类免疫缺陷病毒的感染仍然代表着持续的严重关注和对人类健康的全球威胁。由于多抗性病毒株的出现和所施用的抗逆转录病毒疗法的严重不良副作用，迫切需要开发新的治疗剂，其活性更高，毒性更低并且对突变的耐受性增强。喹喔啉衍生物是一类新兴的杂环化合物，具有广泛的生物学活性和治疗应用。这些类型的化合物还显示出在细胞培养中抑制HIV逆转录酶和HIV复制的高效能。由于这些原因，我们在这项工作中提出了针对HIV逆转录酶的喹喔啉衍生物的设计，合成和生物学评估。为了这，我们首先对喹喔啉衍生物的靶标特异性化合物虚拟化学文库进行了基于结构的开发。虚拟化学库的合理构建基于先前分配的药效团特征。该库通过采用分子对接和3D-QSAR的虚拟筛选方案进行处理。根据对接和3D-QSAR得分以及化学合成的简便性，选择了25种喹喔啉化合物进行合成。他们被评估为重组野生型逆转录酶的抑制剂。最后，评估了具有最高逆转录酶抑制能力的合成喹喔啉化合物的抗HIV活性和细胞毒性。
• Synthesis and Physicochemical Study of a Quinoxaline Derivative with Potencial Antineoplasic or Anti-HIV Activity
  作者：Gabriela Rodrigo、Diana Bekerman、Adriana Robinsohn、Beatriz Fernández

  DOI：10.3390/50300358

  日期：——

  Kinetics of the synthesis of 3-[3-quinoxaline(1H)-one]propionic acid (I) were performed. This compound was achieved from reaction between o-phenylenediamine and α-ketoglutaric acid under different experimental conditions, and it was sent to the National Cancer Institute (USA) for its pharmacological evaluation.

  进行了 3-[3-喹喔啉（1H）-酮]丙酸（I）的合成动力学研究。该化合物是由邻苯二胺和 α-酮戊二酸在不同实验条件下反应生成的，已送交美国国家癌症研究所进行药理评估。