[(2-氧代-2H-苯并吡喃-7-基)氧基]乙酸 | 126424-85-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: [(2-氧代-2H-苯并吡喃-7-基)氧基]乙酸
• 英文名称: 2-((2-oxo-2H-chromen-7-yl)oxy)acetic acid
• 英文别名: 7-(carboxymethoxy)coumarin；[(2-oxo-2H-chromen-7-yl)oxy]acetic acid；2-(2-oxochromen-7-yl)oxyacetic acid
• CAS: 126424-85-9
• 化学式: C₁₁H₈O₅
• mdl: MFCD00695616
• 分子量: 220.182
• InChiKey: YENBPUAYKYLKSL-UHFFFAOYSA-N

物化性质

• 熔点：
  210.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  461.8±45.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2932209090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: [(2-Oxo-2h-chromen-7-yl)oxy]acetic 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: [(2-Oxo-2h-chromen-7-yl)oxy]acetic acid
CAS number: 126424-85-9

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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: C11H8O5
Molecular weight: 220.2

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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.

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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：

  [(2-氧代-2H-苯并吡喃-7-基)氧基]乙酸 在 氯化亚砜 作用下， 以 氯仿 、 水 为溶剂， 反应 2.5h， 生成 N,N-Diethylcoumarin-7-oxyacetamide
  参考文献：
  名称：

  A General Synthesis of Bis[coumarinyl] Ethers: Synthesis of Daphnoretin Methyl Ether

  摘要：

  本文给出了 3,7′-双[香豆素基]醚的一般合成方法。关键步骤包括 N,N-二乙基香豆素-7-氧代乙酰胺和磷酰氯的预形成复合物与取代的水杨醛的反应。此外，还介绍了使用这种方法合成萘皮素甲醚的新方法。

  DOI：

  10.1055/s-1986-31657
• 作为产物：
  描述：

  7-羟基香豆素 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 生成 [(2-氧代-2H-苯并吡喃-7-基)氧基]乙酸
  参考文献：
  名称：

  1,10-菲咯啉和香豆素基草乙酸酯的三元铜 (II) 络合物作为促凋亡 UPR CHOP 诱导剂

  摘要：

  我们制备了六种分子式为 [Cu(phen) 2 (L x )](ClO 4 )( x : 1–6)的配合物，其中辅助配体 L x是在第 6 或第 7 位带有草酰乙酸酯部分的香豆素羧酸酯衍生物，并且第三或第四位有不同的取代基。配合物显示出围绕金属离子的五配位几何形状。在八面体几何结构中完成配位球的可能性使得分子能够进一步反应。复合物主要通过静电相互作用和凹槽结合表现出对DNA的亲和力，而与DNA碱基对的相互作用则由辅助配体保证。杂配体 Cu( II）复合物在微摩尔浓度范围内表现出细胞毒活性，并且机制研究表明它们如何在内皮网水平上干扰，诱导未折叠蛋白反应（UPR）的促凋亡分支。肌动蛋白归一化的 CHOP 与 BiP 密度比表明，新型化合物优先诱导由 CHOP 驱动的促凋亡 UPR 信号传导，以剂量依赖性方式并根据香豆素部分中的取代基。

  DOI：

  10.1039/d3nj01317k

文献信息

• 一类含有生物活性基团的四价铂配合物及其 制备方法
  申请人：东南大学

  公开号：CN105622674B

  公开（公告）日：2018-02-02

  本发明是一类含有生物活性基团的四价铂配合物及其制备方法，所述的四价铂配合物即铂(IV)配合物，其结构如式II所示：式II中，Y为OH或Cl；Bio代表生物活性基团。所述的铂(IV)配合物，按照式III所示的反应式进行，式III中，Y为OH或Cl；Bio‑OH代表具有生物活性的化合物，TBTU代表偶联试剂O‑苯并三氮唑‑N，N，N′，N′‑四甲基脲四氟硼酸，TEA代表催化剂三乙胺，DMF代表溶剂N，N‑二甲基甲酰胺，DMSO代表溶剂二甲亚砜；采用顺铂为八面体底面，在一个轴向位置引入小分子靶向或药物活性基团，另一个轴向位置引入羟基或氯原子，提供具有克服顺铂耐药的抗肿瘤四价铂配合物，以期获得高效低毒的铂(IV)药物。
• Dual P-Glycoprotein and CA XII Inhibitors: A New Strategy to Reverse the P-gp Mediated Multidrug Resistance (MDR) in Cancer Cells
  作者：Elisabetta Teodori、Laura Braconi、Silvia Bua、Andrea Lapucci、Gianluca Bartolucci、Dina Manetti、Maria Novella Romanelli、Silvia Dei、Claudiu T. Supuran、Marcella Coronnello

  DOI：10.3390/molecules25071748

  日期：——

  moiety to target CA XII. Many compounds displayed a dual activity against P-gp and CA XII being active in the Rhd 123 uptake test on K562/DOX cells and in the hCA XII inhibition test. On LoVo/DOX cells, that overexpress both P-gp and CA XII, some coumarin derivatives showed a high MDR reversal effect in Rhd 123 uptake and doxorubicin cytotoxicity enhancement tests. In particular, compounds 7 and 8 showed

  合成了一系列新的 N，N-双（烷醇）胺芳基二酯，并将其作为双重 P-糖蛋白 (P-gp) 和碳酸酐酶 XII 抑制剂 (CA XII) 进行研究。这些杂交体应该能够协同克服癌细胞中 P-gp 介导的多药耐药性 (MDR)。据报道，CA XII 可以调节 P-gp 的外排活性，因为 CA XII 抑制引起的 pH 降低导致 P-gp ATPase 活性显着降低。这里报道的新化合物具有 P-gp 和 CA XII 结合部分。这些杂交体包含在 P-糖蛋白配体中发现的 N,N-双（烷醇）胺二酯支架和香豆素或苯磺酰胺部分以靶向 CA XII。许多化合物显示出针对 P-gp 和 CA XII 的双重活性，在 K562/DOX 细胞的 Rhd 123 摄取测试和 hCA XII 抑制测试中具有活性。在同时过表达 P-gp 和 CA XII 的 LoVo/DOX 细胞上，一些香豆素衍生物在 Rhd 123
• Writing and erasing hidden optical information on covalently modified cellulose paper
  作者：M. d'Halluin、J. Rull-Barrull、E. Le Grognec、D. Jacquemin、F.-X. Felpin

  DOI：10.1039/c6cc02915a

  日期：——

  A strategy for preparing photoresponsive cellulose paper enabling the storage of short-lived optical data by covalent means is disclosed.

  一种通过共价手段存储短寿命光学数据的光响应纤维素纸的制备策略被揭示。
• Synthesis and biological evaluation of CX-659S and its related compounds for their inhibitory effects on the delayed-type hypersensitivity reaction
  作者：Masanori Tobe、Yoshiaki Isobe、Yuso Goto、Fumihiro Obara、Masami Tsuchiya、Junko Matsui、Kosaku Hirota、Hideya Hayashi

  DOI：10.1016/s0968-0896(00)00126-7

  日期：2000.8

  In order to find novel nonsteroidal compounds possessing an inhibitory activity against delayed-type hypersensitivity (DTH) reactions, we conducted random screening using a picryl chloride (PC)-induced contact hypersensitivity reaction (CHR) in mice, and found compound 1 as a lead compound. Then we synthesized and evaluated an extensive series of 5-carboxamidouracil derivatives focused on both the

  为了找到对延迟型超敏反应（DTH）反应具有抑制活性的新型非甾体化合物，我们使用氯化吡啶（PC）诱导的小鼠接触超敏反应（CHR）在小鼠中进行了随机筛选，发现化合物1为铅复合。然后，我们合成并评估了一系列广泛的针对尿嘧啶和抗氧化部分的5-羧酰胺基尿嘧啶衍生物。其中，我们发现受阻酚部分对于展示其活性是必要的。特别地，发现具有维生素E的部分结构的化合物28a-28c通过口服和局部给药都具有针对DTH反应的有效活性。化合物28c对脂质过氧化具有抗氧化活性，IC50为5.9 microM。
• A new convenient route to 2-oxoethoxycoumarins: key intermediates in the synthesis of natural products
  作者：Stefano Chimichi、Marco Boccalini、Barbara Cosimelli

  DOI：10.1016/s0040-4020(02)00442-8

  日期：2002.6

  A new synthetic route to coumarinyloxyaldehydes starting from hydroxycoumarins is presented; these compounds, useful intermediates in the preparation of natural products such as geiparvarin and psoralens, are now available in excellent yields with a simple workup procedure. Moreover the reported route has been applied to dihydroxycoumarins.

  提出了一种从羟基香豆素开始合成香豆素氧基醛的新方法。这些化合物是制备天然产物（如geiparvarin和补骨脂素）中有用的中间体，现在可以通过简单的后处理程序以高收率获得。此外，所报道的途径已经应用于二羟基香豆素。