2-(氯甲基)-5-(3-甲氧基苯基)-1,3,4-恶二唑 | 36770-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(氯甲基)-5-(3-甲氧基苯基)-1,3,4-恶二唑
• 英文名称: 2-Chlormethyl-5-(m-anisyl)-1,3,4-oxadiazol
• 英文别名: 2-(Chloromethyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole
• CAS: 36770-18-0
• 化学式: C₁₀H₉ClN₂O₂
• mdl: MFCD08753714
• 分子量: 224.647
• InChiKey: WQEYFJNCHQGZEX-UHFFFAOYSA-N

物化性质

• 沸点：
  364.6±52.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(Chloromethyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole
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-(Chloromethyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole
CAS number: 36770-18-0

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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, refrigerated.
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: C10H9ClN2O2
Molecular weight: 224.6

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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, hydrogen chloride.

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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-(氯甲基)-5-(3-甲氧基苯基)-1,3,4-恶二唑 、 诺氟沙星 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 生成 1-Ethyl-6-fluoro-7-[4-[[5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  设计和合成新的诺氟沙星-1,3,4-恶二唑杂种作为对耐甲氧西林的金黄色葡萄球菌（MRSA）的抗菌剂。

  摘要：

  为了寻找新的抗菌药物来控制耐甲氧西林的金黄色葡萄球菌（MRSA），设计并合成了一类新的诺氟沙星-1,3,4-恶二唑杂种。评估了对药物敏感细菌金黄色葡萄球菌和MRSA临床耐药菌株的抗菌活性。化合物5k对金黄色葡萄球菌（MIC：2μg/ mL）和MRSA1-3（MIC：0.25-1μg/ mL）表现出优异的抗菌活性。时间杀灭动力学表明，化合物5k在杀死金黄色葡萄球菌和MRSA方面优于常用抗生素万古霉素。而且，化合物5k可以在短时间内抑制细菌并破坏其膜，并且对NRK-52E细胞显示出非常低的细胞毒性。还讨论了一些有趣的结构-活性关系（SAR）。这些结果表明这些诺氟沙星1,3，

  DOI：

  10.1016/j.ejps.2019.104966
• 作为产物：
  描述：

  3-Methoxy-benzoic acid N'-(2-chloro-acetyl)-hydrazide 在 三氯氧磷 作用下， 生成 2-(氯甲基)-5-(3-甲氧基苯基)-1,3,4-恶二唑
  参考文献：
  名称：

  设计和合成新的诺氟沙星-1,3,4-恶二唑杂种作为对耐甲氧西林的金黄色葡萄球菌（MRSA）的抗菌剂。

  摘要：

  为了寻找新的抗菌药物来控制耐甲氧西林的金黄色葡萄球菌（MRSA），设计并合成了一类新的诺氟沙星-1,3,4-恶二唑杂种。评估了对药物敏感细菌金黄色葡萄球菌和MRSA临床耐药菌株的抗菌活性。化合物5k对金黄色葡萄球菌（MIC：2μg/ mL）和MRSA1-3（MIC：0.25-1μg/ mL）表现出优异的抗菌活性。时间杀灭动力学表明，化合物5k在杀死金黄色葡萄球菌和MRSA方面优于常用抗生素万古霉素。而且，化合物5k可以在短时间内抑制细菌并破坏其膜，并且对NRK-52E细胞显示出非常低的细胞毒性。还讨论了一些有趣的结构-活性关系（SAR）。这些结果表明这些诺氟沙星1,3，

  DOI：

  10.1016/j.ejps.2019.104966

文献信息

• Synthesis and Biological Evaluation of Honokiol Derivatives Bearing 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3H)-ones as Potential Viral Entry Inhibitors against SARS-CoV-2
  作者：Yong Guo、Jie-Ru Meng、Jia-Zheng Liu、Ting Xu、Zhi-Yuan Zheng、Zhi-Hong Jiang、Li-Ping Bai

  DOI：10.3390/ph14090885

  日期：——

  damp-drying effect. To develop new potent antiviral molecules, a series of novel honokiol analogues were synthesized by introducing various 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3H)-ones to its molecule. In a SARS-CoV-2 pseudovirus model, all honokiol derivatives were examined for their antiviral entry activities. As a result, 6a and 6p demonstrated antiviral entry effect with IC50 values of 29

  由 SARS-CoV-2 病毒感染引起的 2019 冠状病毒病 (COVID-19) 对全球健康和经济构成了严重威胁。然而，特异性和有效的 SARS-CoV-2 药物仍在开发中。Honokiol 是一种来自厚朴的生物活性成分，具有燥湿作用。为了开发新的有效抗病毒分子，通过引入各种 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2( 3H )-ones合成了一系列新的和厚朴酚类似物。它的分子。在 SARS-CoV-2 假病毒模型中，检查了所有和厚朴酚衍生物的抗病毒进入活性。结果，6a和6p证明了 IC 50 的抗病毒进入作用值分别为 29.23 和 9.82 µM。然而，亲本和厚朴酚具有非常弱的抗病毒活性，IC 50值超过 50 µM。生物层干涉仪 (BLI) 结合测定和分子对接研究表明，6p与人 ACE2 蛋白的结合比亲代和厚朴酚具有更高的结合亲和力和更低的结合能。一项竞争性
• Discovery of honokiol thioethers containing 1,3,4-oxadiazole moieties as potential α-glucosidase and SARS-CoV-2 entry inhibitors
  作者：Ting Xu、Jie-Ru Meng、Wanqing Cheng、Jia-Zheng Liu、Junyan Chu、Qian Zhang、Nannan Ma、Li-Ping Bai、Yong Guo

  DOI：10.1016/j.bmc.2022.116838

  日期：2022.8

  the binding of SARS-CoV-2 to the host ACE2 receptor through dual recognition of SARS-CoV-2 spike RBD and human ACE2. Additionally, the potent honokiol thioethers 7l, 9a, and 9r displayed relatively no cytotoxicity to normal cells (LO2). These findings will provide a theoretical basis for the discovery of honokiol derivatives as potential both α-glucosidase and SARS-CoV-2 entry inhibitors.

  Honokiol 从中药 (TCM)厚朴中分离出来，是一种具有多种生物活性的双酚类化合物。为了改善和扩大其生物活性，本文制备了两个系列的带有 1,3,4-恶二唑部分的和厚朴酚硫醚，并评估了它们的α-葡萄糖苷酶和 SARS-CoV-2 进入抑制活性。在所有和厚朴酚硫醚中，化合物7l表现出最强的α-葡萄糖苷酶抑制作用，IC 50值为18.9 ± 2.3 µM，优于参比药物阿卡波糖（IC 50 = 24.4 ± 0.3 µM)。还讨论了构效关系 (SAR) 的一些有趣结果。酶动力学研究表明7l是一种非竞争性α-葡萄糖苷酶抑制剂，分子对接结果进一步支持了这一点。此外，和厚朴酚硫醚7e、9a、9e和9r对进入 HEK-293 T-ACE2 h的 SARS-CoV-2 假病毒表现出有效的抗病毒活性。特别是9a对 SARS-CoV-2 假病毒进入具有最强的抑制活性，IC为 50值为 16.96 ± 2.45
• Synthesis and antitumor activities of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing Schiff base moiety
  作者：Kai Zhang、Peng Wang、Li-Na Xuan、Xiao-Yun Fu、Fen Jing、Sha Li、Yu-Ming Liu、Bao-Quan Chen

  DOI：10.1016/j.bmcl.2014.09.086

  日期：2014.11

  A series of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing Schiff base moiety were designed, synthesized and evaluated for their in vitro antitumor activities against SMMC-7721, MCF-7 and A549 human tumor cell lines by CCK-8 assay. The bioassay results demonstrated that most of the tested compounds showed potent antitumor activities, and some compounds exhibited stronger effects than positive control 5-fluorouracil (5-FU) against various cell lines. Among these compounds, compound 8d showed the best inhibitory effect against SMMC-7721 cells, with IC50 value of 2.84 mu M. Compounds 8k and 8n displayed highly effective antitumor activities against MCF-7 cells, with IC50 values of 4.56 and 4.25 mu M, respectively. Compounds 8a and 8n exhibited significant antiproliferative activity against A549 cells, with IC50 values of 4.11 and 4.13 mu M, respectively. The pharmacological results suggest that the substituents of phenyl ring on the 1,3,4-oxadiazole are vital for modulating antiproliferative activities against various tumor cell lines. (C) 2014 Elsevier Ltd. All rights reserved.
• Microwave‐Assisted One‐Step Synthesis of Substituted 2‐Chloromethyl‐1,3,4‐oxadiazoles
  作者：Reina Natero、Dmitry O. Koltun、Jeffery A. Zablocki

  DOI：10.1081/scc-200025582

  日期：2004.1.1

  We have developed a simple one-step synthesis of 2-chloromethyl-1,3,4-oxadiazoles from commercially available acylhydrazides using 1-chloro-2,2,2-trimethoxyethane as a solvent under microwave irradiation.
• Novel 5,6-diphenyl-1,2,4-triazine-3-thiol derivatives as dual COX-2/5-LOX inhibitors devoid of cardiotoxicity
  作者：Poorvi Saraf、Prabhash Nath Tripathi、Manish Kumar Tripathi、Avanish Tripathi、Himanshu Verma、Digambar Kumar Waiker、Royana Singh、Sushant Kumar Shrivastava

  DOI：10.1016/j.bioorg.2022.106147

  日期：2022.12