5-羟基-2-苯基苯并呋喃-3-羧酸乙酯 | 4610-75-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 中文名称: 5-羟基-2-苯基苯并呋喃-3-羧酸乙酯
• 英文名称: ethyl 5-hydroxy-2-phenylbenzofuran-3-carboxylate
• 英文别名: 5-Hydroxy-2-phenyl-benzofuran-3-carboxylic acid ethyl ester；ethyl 5-hydroxy-2-phenyl-1-benzofuran-3-carboxylate
• CAS: 4610-75-7
• 化学式: C₁₇H₁₄O₄
• mdl: MFCD00631149
• 分子量: 282.296
• InChiKey: WZZJQHPNLFLEMB-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C(Solv: acetic acid (64-19-7))
• 沸点：
  471.3±45.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.117
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 5-hydroxy-2-phenylbenzofuran-3-carboxylate
Synonyms: 5-Hydroxy-2-phenyl-benzofuran-3-carboxylic acid ethyl ester

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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: Ethyl 5-hydroxy-2-phenylbenzofuran-3-carboxylate
CAS number: 4610-75-7

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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: C17H14O4
Molecular weight: 282.3

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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.

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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：

  5-羟基-2-苯基苯并呋喃-3-羧酸乙酯 在 1,4-二氧六环 、 sodium hydroxide 、 硫酸 、 溶剂黄146 作用下， 生成 2-phenyl-5-methoxybenzo[b]furan
  参考文献：
  名称：

  Grinew et al., Zhurnal Obshchei Khimii, 1958, vol. 28, p. 1853; engl. Ausg. S. 1897

  摘要：

  DOI：
• 作为产物：
  描述：

  对苯二酚 在 potassium bromate 、 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 12.25h， 生成 5-羟基-2-苯基苯并呋喃-3-羧酸乙酯
  参考文献：
  名称：

  Design, synthesis, docking and anti-inflammatory evaluation of novel series of benzofuran based prodrugs

  摘要：

  Several new benzofuran derivatives were synthesized, via appropriate synthetic route as anti-inflammatory agents. The anti-inflammatory activity of the prepared compounds was evaluated using carrageenan rat model. Among the synthesized compounds, some compounds showed comparable anti-inflammatory activity to nimesulide, the standard drug taken for anti-inflammatory studies. Docking study of the prepared compounds was performed for the study of interaction of molecules with the active site of COX-2. Preliminary biological studies and docking gave an interesting insight, into the validity of employing benzofuran analogues as good anti-inflammatory agent. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.087

文献信息

• Benzofuran derivatives as anticancer inhibitors of mTOR signaling
  作者：Christophe Salomé、Nigel Ribeiro、Thierry Chavagnan、Frédéric Thuaud、Maria Serova、Armand de Gramont、Sandrine Faivre、Eric Raymond、Laurent Désaubry

  DOI：10.1016/j.ejmech.2014.05.014

  日期：2014.6

  A series of 32 derivatives and isosteres of the mTOR inhibitor 2 were synthesized and compared for their cytotoxicity in radioresistant SQ20B cancer cell line. Several of these compounds, in particular 30b, were significantly more cytotoxic than 2. Importantly, 30b was shown to block both mTORC1 and Akt signaling, suggesting insensitivity to the resistance associated to Akt overactivation observed

  合成了一系列32种mTOR抑制剂2的衍生物和等排物，并比较了它们在抗放射SQ20B癌细胞系中的细胞毒性。这些化合物中的几种，特别是30b，比2具有明显更高的细胞毒性。重要的是，显示30b可以同时阻断mTORC1和Akt信号传导，表明对目前在临床上使用的雷帕霉素衍生物观察到的与Akt过度活化相关的抗药性不敏感。
• Identification of Novel Coumestan Derivatives as Polyketide Synthase 13 Inhibitors against <i>Mycobacterium tuberculosis</i>
  作者：Wei Zhang、Shichun Lun、Shu-Huan Wang、Xing-Wu Jiang、Fan Yang、Jie Tang、Abigail L. Manson、Ashlee M. Earl、Hendra Gunosewoyo、William R. Bishai、Li-Fang Yu

  DOI：10.1021/acs.jmedchem.7b01319

  日期：2018.2.8

  Inhibition of the mycolic acid pathway has proven a viable strategy in antitubercular drug discovery. The AccA3/AccD4/FadD32/Pks13 complex of Mycobacterium tuberculosis constitutes an essential biosynthetic mechanism for mycolic acids. Small molecules targeting the thioesterase domain of Pks13 have been reported, including a benzofuran-based compound whose X-ray cocrystal structure has been very recently

  霉菌酸途径的抑制已被证明是抗结核药物发现中的可行策略。结核分枝杆菌的AccA3 / AccD4 / FadD32 / Pks13复合体构成霉菌酸必不可少的生物合成机制。已经报道了靶向Pks13的硫酯酶结构域的小分子，包括基于苯并呋喃的化合物，其X射线共晶体结构最近已得到解决。它最初在血清抑制滴定（SIT）分析中不起作用，导致我们进一步探查其他与结构相关的苯并呋喃，以提高其效价和生物利用度。在此，我们报告了围绕该支架的初步结构-活性关系研究，强调了天然产物启发的环化策略，以形成在SIT中表现出活性的香豆素。耐coumestan突变体的全基因组深度测序中所确认的单核苷酸多态性pks13 该基因负责抵抗表型，证明该靶标可用于开发新型抗结核药物。
• Benzofuran‐isatin conjugates as potent VEGFR‐2 and cancer cell growth inhibitors
  作者：Yulin Zou

  DOI：10.1002/jhet.3795

  日期：2020.1

  that VEGFR‐2 was at least one of the targets for this kind of conjugates. The structure‐activity relationship demonstrated that the carbon spacer between benzofuran and isatin moieties, substituents on the C‐2 position of benzofuran moiety, and substituents on C‐3 as well as C‐5 position of isatin motif influenced the anticancer activity significantly, and the enriched structure‐activity relationship

  一系列苯并呋喃-依斯丁共轭物6a-1和7a，b合成了由各种烷基接头束缚的分子，并评估了它们对一组癌细胞系的VEGFR-2抑制活性和体外活性。在所有测试的癌细胞中，其中有七个与舒尼替尼相当或优于舒尼替尼，表明苯并呋喃-依斯丁共轭物是潜在的抗癌候选物。机理研究表明，VEGFR-2至少是这类结合物的靶标之一。构效关系表明，苯并呋喃与靛红部分之间的碳间隔基，苯并呋喃部分C-2位置的取代基，C-3以及取代基基序的C-5位置上的取代基显着影响了抗癌活性，并且丰富的结构-活性关系可以为更有效结合物的合理设计提供见识。
• DESIGN, SYNTHESIS AND IN VITRO ANTI-BACTERIAL ACTIVITIES OF BENZOFURAN-ISATIN HYBRIDS
  作者：Yin-Ling WANG、Shi-Jia ZHAO、Yi LIU、Zhi XU

  DOI：10.33224/rrch/2019.64.8.6

  日期：——

  of novel benzofuran-isatin hybrids 6a-x tethered through propylene, butylene, pentylene and hexylene were designed, synthesized and evaluated for their in vitro antibacterial activities against a panel of clinically important Grampositive and Gram-negative pathogens including drug-resistant bacteria. All hybrids exhibited decent in vitro anti-bacterial activities, and the most active hybrid 6l was not

  设计，合成和评估了一系列通过丙烯，丁烯，戊烯和己烯系链的新型苯并呋喃-靛红素杂种6a-x，它们针对一系列临床上重要的革兰氏阳性和革兰氏阴性病原体（包括耐药菌）的体外抗菌活性。所有杂种均表现出良好的体外抗菌活性，活性最高的杂种6l不仅对大多数测试的革兰氏阳性菌具有与万古霉素相当的功效，而且对革兰氏阴性菌也具有很高的活性。基于以上结果，杂种6l可以作为进一步研究的线索。而且，丰富的构效关系可以为进一步优化铺平道路。
• 一类苯并呋喃及苯并呋喃香豆素衍生物及其制备方法和应用
  申请人：华东师范大学

  公开号：CN109942523B

  公开（公告）日：2023-06-09

  本发明公开了如式(I)、(II)、(III)、(IV)所示的苯并呋喃类及Coumestans衍生物及其制备方法，以及所述苯并呋喃类及Coumestans衍生物化合物在治疗耐多药性肺结核疾病中的应用。本发明所述苯并呋喃类及Coumestans衍生物是一类结构新颖，抑菌效果显著的抗结核杆菌化合物，它是以结核杆菌pks13基因片段编码的聚酮合酶为作用靶点，抑制微生物的生长繁殖，尤其是抑制结核分枝杆菌细胞壁中分枝菌酸的合成，在医药领域具有潜在的应用前景。