5-(4-甲氧苯基)-2-糠酸 | 52938-99-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 5-(4-甲氧苯基)-2-糠酸
• 中文别名: 5-(4-甲氧基苯基)呋喃-2-羧酸
• 英文名称: 5-(4-methoxyphenyl)furan-2-carboxylic acid
• 英文别名: 5-(4-Methoxyphenyl)-2-furoic acid
• CAS: 52938-99-5
• 化学式: C₁₂H₁₀O₄
• mdl: MFCD03937477
• 分子量: 218.209
• InChiKey: YEBLYHKPTQJGEC-UHFFFAOYSA-N

物化性质

• 熔点：
  182-186 °C (dec.)(lit.)
• 沸点：
  401.5±40.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2932190090
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。应储存在阴凉、干燥的地方。

SDS

Name:	5-(4-Methoxyphenyl)-2-furoic acid Material Safety Data Sheet
Synonym:	None Known.
CAS:	52938-99-5

Section 1 - Chemical Product MSDS Name: 5-(4-Methoxyphenyl)-2-furoic acid Material Safety Data Sheet
Synonym: None Known.

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
52938-99-5	5-(4-Methoxyphenyl)-2-furoic acid	97+	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Irritating to eyes, respiratory system and skin. Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

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SECTION 4 - FIRST AID MEASURES
Eyes:
Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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SECTION 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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SECTION 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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SECTION 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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SECTION 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 52938-99-5: Personal Protective Equipment
Eyes:
Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES
Physical State: Solid
Color: off-white
Odor: odorless
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 176-178.5 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H10O4
Molecular Weight: 218.21

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, bases, amines.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 52938-99-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-(4-Methoxyphenyl)-2-furoic acid - Not listed by ACGIH, IARC, or NTP.

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SECTION 12 - ECOLOGICAL INFORMATION

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SECTION 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations.

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SECTION 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material.

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SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system and skin.
Safety Phrases:
S 22 Do not breathe dust. S 26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36/37/39 Wear suitable protective clothing, gloves and eye/face protection. WGK (Water Danger/Protection) CAS# 52938-99-5: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 52938-99-5 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 52938-99-5 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 5/20/2004 Revision #1 Date: 5/20/2004 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-(4-甲氧苯基)-2-糠酸 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (5-(4-methoxyphenyl)furan-2-yl)methanol
  参考文献：
  名称：

  潜在的PDE4抑制剂苯基取代的呋喃和恶唑羧酸衍生物的合成及生物活性

  摘要：

  在本研究中，设计并合成了一系列5-苯基-2-呋喃和4-苯基-2-恶唑衍生物，作为4型磷酸二酯酶（PDE4）抑制剂。体外结果表明，合成的化合物对PDE4B表现出相当大的抑制活性，并阻断LPS诱导的TNF- α释放。在设计的化合物中，化合物5j在体外酶法检测中对PDE4的IC 50值（1.4μM）低于母体咯利普兰（2.0μM），在体内也显示出良好的LPS诱发的哮喘/ COPD和败血症动物模型中的活性降低。对接结果表明，在苯环对位引入甲氧基，表现出与PDE4B的金属结合口袋结构域良好的相互作用，这有助于增强抑制活性。

  DOI：

  10.1016/j.ejmech.2020.112795
• 作为产物：
  描述：

  5-溴-2-糠酸甲酯 在 四(三苯基膦)钯 、 sodium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 5.5h， 生成 5-(4-甲氧苯基)-2-糠酸
  参考文献：
  名称：

  5-芳基-呋喃-2-羧酰胺衍生物的合成和合成孔径雷达作为有效的尿紧张素-II受体拮抗剂。

  摘要：

  一系列4-（3-氯-4-（哌啶丁-4-基氧基）苄基）哌嗪-1的5-芳基呋喃-2-羧酰胺衍生物1的合成和生物学评价，作为潜在的尿紧张素II受体拮抗剂。描述了基团。对具有C-5芳基且具有多个芳环取代基的呋喃-2-甲酰胺进行系统SAR研究的结果导致鉴定3,4-二氟苯基类似物1y为高效UT拮抗剂，IC50值为6 nM。另外，发现该物质表现出高的代谢稳定性，低的hERG抑制和细胞毒性，并具有可接受的PK曲线。

  DOI：

  10.1016/j.bmcl.2018.12.058

文献信息

• Novel <i>S</i>-Thiazol-2-yl-furan-2-carbothioate Derivatives as Potential T3SS Inhibitors Against <i>Xanthomonas oryzae</i> on Rice
  作者：Shan Jiang、Min He、Xu-Wen Xiang、Muhammad Adnan、Zi-Ning Cui

  DOI：10.1021/acs.jafc.9b04085

  日期：2019.10.30

  significantly attenuated HR without affecting bacterial growth. The mRNA levels of some representative genes (hrp/hrc genes) were reduced up to different extents. In vivo bioassay results showed that eight T3SS inhibitors could reduce bacterial leaf blight and bacterial leaf streak symptoms on rice, significantly.

  水稻黄单胞菌（Xanthomonas oryzae）造成的细菌性叶枯病（BLB）被认为是水稻最具破坏性的疾病。杀菌剂的使用是控制这种破坏性疾病的最广泛使用的传统方法之一。过度使用和重复使用相同的杀菌剂也成为产生抗药性的原因。寻找新的抗微生物剂的广泛使用的方法通常将细菌毒力因子作为目标，而不影响细菌的生长。III型分泌系统（T3SS）是一种蛋白质附件，在大多数革兰氏阴性细菌中被认为具有必需的毒力因子。由于保守的构建，T3SS被认为是新的抗菌药物泛滥的重要标志。为了寻找新的T3SS抑制剂，设计和合成了另一系列的1,3-噻唑衍生物。通过1 H NMR，13 C NMR，MS和元素分析对它们的结构进行了表征和确认。所有标题化合物均显着抑制hpa1基因的启动子活性。他们中的八个显示出比我们以前的T3SS抑制剂TS006（邻香豆酸，OCA）更好的抑制作用。用八种化合物处理Xoo可以显着降低HR，而不会影响细菌的生长。一些代表性基因（hrp
• Discovery of a series of 5-phenyl-2-furan derivatives containing 1,3-thiazole moiety as potent Escherichia coli β-glucuronidase inhibitors
  作者：Tao-Shun Zhou、Lu-Lu He、Jing He、Zhi-Kun Yang、Zhen-Yi Zhou、Ao-Qi Du、Jin-Biao Yu、Ya-Sheng Li、Si-Jia Wang、Bin Wei、Zi-Ning Cui、Hong Wang

  DOI：10.1016/j.bioorg.2021.105306

  日期：2021.11

  evaluated for their inhibitory effects against Escherichia coli β-glucuronidase (EcGUS). Twelve of them showed satisfactory inhibition against EcGUS with IC50 values ranging from 0.25 μM to 2.13 μM with compound 12 exhibited the best inhibition. Inhibition kinetics studies indicated that compound 12 (Ki = 0.14 ± 0.01 μM) was an uncompetitive inhibitor for EcGUS and molecular docking simulation further predicted

  肠道微生物 β-葡萄糖醛酸酶因其作为减轻某些药物或其代谢物引起的胃肠道毒性的潜在治疗靶标的作用而备受关注。在这项研究中，含有1,3-噻唑基部分15 5-苯基-2-呋喃衍生物（1 - 15合成并评价了它们对抑制效果）大肠杆菌β葡糖醛酸酶（EcGUS）。其中 12 种对 EcGUS 表现出令人满意的抑制作用，IC 50值范围为 0.25 μM 至 2.13 μM，其中化合物12表现出最佳抑制作用。抑制动力学研究表明，化合物12 (K i = 0.14 ± 0.01 μM) 是 EcGUS 的非竞争性抑制剂，分子对接模拟进一步预测了化合物12与 EcGUS的结合模型和能力。初步的结构抑制活性关系研究表明，苯的杂环骨架和溴取代可能对抑制 EcGUS 至关重要。这些化合物有可能应用于药物引起的胃肠道毒性，研究结果将有助于研究人员设计和开发更有效的 5-苯基-2-呋喃型 EcGUS 抑制剂。
• Derivatives of (<i>R</i>)-3-(5-Furanyl)carboxamido-2-aminopropanoic Acid as Potent NMDA Receptor Glycine Site Agonists with GluN2 Subunit-Specific Activity
  作者：Fabao Zhao、Unai Atxabal、Sofia Mariottini、Feng Yi、James S. Lotti、Nirvan Rouzbeh、Na Liu、Lennart Bunch、Kasper B. Hansen、Rasmus P. Clausen

  DOI：10.1021/acs.jmedchem.1c01810

  日期：2022.1.13

  potencies and agonist efficacies among the NMDA receptor subtypes (GluN1/2A–D) in a manner dependent on the GluN2 subunit. Notably, compound 8p is identified as a potent partial agonist at GluN1/2C (EC50 = 0.074 μM) with an agonist efficacy of 28% relative to activation by Gly and virtually no agonist activity at GluN1/2A, GluN1/2B, and GluN1/2D. Thus, these novel agonists can modulate the activity of specific

  NMDA 受体介导谷氨酸能神经传递，并且由于它们参与多种精神和神经疾病而成为治疗靶点。在这里，我们描述了一系列 ( R )-3-(5-furanyl)carboxamido-2-aminopropanoic acid analogues 8a – s作为 GluN1 亚基甘氨酸 (Gly) 结合位点激动剂的设计和合成，但不是NMDA 受体的 GluN3 亚基。这些新型类似物以依赖于 GluN2 亚基的方式在 NMDA 受体亚型 (GluN1/2A–D) 中显示出高度可变的效力和激动剂功效。值得注意的是，化合物8p被鉴定为 GluN1/2C (EC 50= 0.074 μM)，相对于 Gly 激活的激动剂功效为 28%，并且在 GluN1/2A、GluN1/2B 和 GluN1/2D 上几乎没有激动剂活性。因此，这些新型激动剂可以通过替代完全内源性激动剂 Gly 或d-丝氨酸 ( d -Ser)来调节特定
• Selective Inhibition of DNA Polymerase β by a Covalent Inhibitor
  作者：Shelby C. Yuhas、Daniel J. Laverty、Huijin Lee、Ananya Majumdar、Marc M. Greenberg

  DOI：10.1021/jacs.1c02453

  日期：2021.6.2

  has been closely linked to cancer. Selective inhibitors of this enzyme are lacking. Inspired by DNA lesions produced by antitumor agents that inactivate Pol β, we have undertaken the development of covalent small-molecule inhibitors of this enzyme. Using a two-stage process involving chemically synthesized libraries, we identified a potent irreversible inhibitor (14) of Pol β (KI = 1.8 ± 0.45 μM, kinact

  DNA 聚合酶 β (Pol β) 在 DNA 修复中起着至关重要的作用，并且与癌症密切相关。缺乏这种酶的选择性抑制剂。受使 Pol β 失活的抗肿瘤剂产生的 DNA 损伤的启发，我们着手开发这种酶的共价小分子抑制剂。使用涉及化学合成文库的两阶段过程，我们确定了Pol β的有效不可逆抑制剂 ( 14 ) ( K I = 1.8 ± 0.45 μM, k inact = (7.0 ± 1.0) × 10 –3 s –1 )。抑制剂14比其他 DNA 聚合酶选择性地灭活 Pol β。用14处理的 Pol β 胰蛋白酶消化物的 LC-MS/MS 分析鉴定了聚合酶结合位点内共价修饰的两个赖氨酸，其中一个先前被确定在DNA结合中起作用。荧光各向异性实验表明，用14预处理 Pol β可防止 DNA 结合。在野生型小鼠胚胎成纤维细胞 (MEF) 中使用前抑制剂 ( pro - 14 ) 的实验表明，抑制剂
• Synthesis and antimicrobial activities of some new triazolothiadiazoles bearing 4-methylthiobenzyl moiety
  作者：D. Jagadeesh Prasad、Mithun Ashok、Prakash Karegoudar、Boja Poojary、B. Shivarama Holla、Nalilu Sucheta Kumari

  DOI：10.1016/j.ejmech.2008.03.025

  日期：2009.2

  synthesized by condensing 4-amino-3-[4-methylthiobenzyl]-4H-1,2,4-triazole-5-thiol (5) with substituted aryl furoic acids/aromatic acids in the presence of POCl3. The triazole (5) was obtained by the fusion of 4-methylthiophenyl acetic acid (4) with thiocarbohydrazide. The structures of newly synthesized compounds are characterized by elemental analysis, IR, 1H NMR and mass spectroscopic studies and were screened

  通过将4-氨基-3- [4-甲基硫代苄基] -4 H -1,2,4-三唑-5-硫醇（5）与取代基缩合，合成了一系列取代的三唑并二唑（6a – j和7a – j）。POCl 3存在下的芳基糠酸/芳酸。通过使4-甲基硫代苯基乙酸（4）与硫代碳酰肼熔融，得到三唑（5）。 通过元素分析，IR，1 H NMR和质谱研究对新合成化合物的结构进行表征，并筛选其抗菌活性。初步结果表明，某些化合物显示出有希望的抗菌活性。