3-(4-溴苯基)-5-(氯甲基)-1,2,4-噁二唑 | 110704-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(4-溴苯基)-5-(氯甲基)-1,2,4-噁二唑
• 中文别名: 3-(4-溴苯基)-5-(氯甲基)-1,2,4-恶二唑
• 英文名称: 3-(4-bromophenyl)-5-(chloromethyl)-1,2,4-oxadiazole
• CAS: 110704-42-2
• 化学式: C₉H₆BrClN₂O
• mdl: MFCD08445385
• 分子量: 273.516
• InChiKey: QBGZOSPLOUPRQG-UHFFFAOYSA-N

物化性质

• 熔点：
  63-65°

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(4-Bromophenyl)-5-(chloromethyl)-1,2,4-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: 3-(4-Bromophenyl)-5-(chloromethyl)-1,2,4-oxadiazole
CAS number: 110704-42-2

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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: C9H6BrClN2O
Molecular weight: 273.5

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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, hydrogen bromide.

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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-(4-溴苯基)-5-(氯甲基)-1,2,4-噁二唑 在 sodium azide 作用下， 生成 5-(azidomethyl)-3-(4-bromophenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  一些带有1,2,4-恶二唑和1,2,3-三唑部分的氮杂大环的合成

  摘要：

  摘要从1,4开始合成了一个在两个氮原子上带有炔丙基的四氮杂row醚4,9-二（prop-2-yn-1-yl）-1,4,9,12-四氮杂环十六烷-2,11-二酮，9，12-四氮杂环十六烷-2，11-二酮并与通过酰化制备的5-（叠氮甲基）-3-（4-R-苯基）-1，2，4-恶二唑进行1，3-环加成反应。将相应的对位取代的苯甲酰胺肟与氯乙酰氯混合，然后进行叠氮化。以这种方式，成功地获得了一系列带有1,2,4-恶二唑和1,2,3-三唑环的氮杂皇冠醚，并通过光谱/物理数据阐明了它们的结构。

  DOI：

  10.1134/s1070428020040193
• 作为产物：
  描述：

  (E)-4-溴-N’-羟基苄脒 以 甲苯 为溶剂， 生成 3-(4-溴苯基)-5-(氯甲基)-1,2,4-噁二唑
  参考文献：
  名称：

  与zopolrestat有关的有效的口服活性醛糖还原酶抑制剂：苯并噻唑侧链的替代物。

  摘要：

  为了寻找有效的醛糖还原酶抑制剂zopolrestat（1）的关键苯并噻唑侧链的有效替代物，进行了广泛的结构活性程序。追求结构驱动的方法，该方法涵盖了三个领域的探索：（1）5/6稠合杂环，如苯并恶唑，苯并噻吩，苯并呋喃和咪唑并吡啶；（2）5元杂环，包括带有侧基芳基的恶二唑，恶唑，噻唑和噻二唑，以及（3）苯并噻唑的形式当量的硫代苯胺。在糖尿病并发症的一项急性试验中，发现几种苯并恶唑和1,2,4-恶二唑衍生的类似物是有效的人胎盘醛糖还原酶抑制剂，并且在防止大鼠坐骨神经中山梨醇蓄积方面具有口服活性。3,4-Dihydro-4-oxo-3-[（5，（7-二氟-2-苯并恶唑基）甲基] -1-酞嗪乙酸（124）是苯并恶唑系列中最好的（IC50 = 3.2 x 10（-9）M）; 当口服剂量为10 mg / kg时，它可将山梨醇在大鼠坐骨神经中的蓄积抑制78％。化合物139，3,4-二氢-4-氧代-3-[[[（（2-氟苯基）-1

  DOI：

  10.1021/jm00081a006

文献信息

• Design, Synthesis, Biological Evaluation, and Docking Study of Acetylcholinesterase Inhibitors: New Acridone-1,2,4-oxadiazole-1,2,3-triazole Hybrids
  作者：Maryam Mohammadi-Khanaposhtani、Mohammad Mahdavi、Mina Saeedi、Reyhaneh Sabourian、Maliheh Safavi、Mahnaz Khanavi、Alireza Foroumadi、Abbas Shafiee、Tahmineh Akbarzadeh

  DOI：10.1111/cbdd.12609

  日期：2015.12

  this study, novel acridone‐1,2,4‐oxadiazole‐1,2,3‐triazole hybrids were designed, synthesized, and evaluated for their acetylcholinesterase and butyrylcholinesterase inhibitory activity. Among various synthesized compounds, 10‐((1‐((3‐(4‐methoxyphenyl)‐1,2,4‐oxadiazol‐5‐yl)methyl)‐1H‐1,2,3‐triazol‐4‐yl)methyl)acridin‐9(10H)‐one 10b showed the most potent anti‐acetylcholinesterase activity (IC50 = 11.55 μm)

  在这项研究中，设计，合成并评估了新的a啶酮1,2,4，恶二唑1,2,3-三唑杂合体的乙酰胆碱酯酶和丁酰胆碱酯酶抑制活性。在各种合成的化合物中，10-（（1-（（3-（4--甲氧基苯基）-1,2,4-恶二唑-5-基）甲基）-1 H -1,2,3-三唑-4-基）甲基）吖啶-9-（10 ħ） -酮10b中显示出最有效的抗乙酰胆碱酯酶活性（IC 50  = 11.55  μ米）是一样有效的利凡斯的明。对接结果也与体外结果高度吻合，证实了化合物10b的双重结合抑制活性。
• Synthesis of novel triazoles bearing 1,2,4-oxadiazole and phenylsulfonyl groups by 1,3-dipolar cycloaddition of some organic azides and their biological activities
  作者：Yaşar DÜRÜST、Hamza KARAKUŞ、Muhsine Zeynep YAVUZ、Ali Akçahan GEPDİREMEN

  DOI：10.3906/kim-1309-59

  日期：——

  1,3-Dipolar cycloaddition of 5-azidomethyl-3-p-substituted phenyl-1,2,4-oxadiazoles to phenyl vinyl sulfone and bismaleimide gives rise straightforwardly to 1-((3-(p-substituted) phenyl-1,2,4-oxadiazol-5-yl)methyl)-4-(phenylsul\-fonyl)-4,5-dihydro-1H-1,2,3-triazoles and bisdihydropyrrolo[3,4-d][1,2,3]triazole-4,6(3aH,5H)-diones. The structures of the new cycloadducts were elucidated by means of IR, NMR (^1H, ^13}C, 2D), mass spectra, and physical characteristics (mp and R_f values). In addition, anticancer activities of the cycloadducts against MCF-7 cells were also investigated.

  5-叠氮甲基-3-对取代苯基-1,2,4-嗯二唑与苯基乙烯砜和双马来酰亚胺的1,3-偶极环加成反应，直接生成1-((3-(对取代)苯基-1,2,4-嗯二唑-5-基)甲基)-4-(苯磺酰基)-4,5-二氢-1H-1,2,3-三唑和双二氢吡咯并[3,4-d][1,2,3]三唑-4,6(3aH,5H)-二酮。通过红外、核磁共振(^1H、^13C、2D)、质谱和物理性质(熔点和R_f值)阐明了新环加合物的结构。此外，还研究了这些环加合物对MCF-7细胞的抗癌活性。
• Design, Synthesis and Cytotoxicity of Novel Coumarin-1,2,3-triazole-1,2,4- Oxadiazole Hybrids as Potent Anti-breast Cancer Agents
  作者：Maryam Mohammadi-Khanaposhtani、Kiana Fahimi、Elahe Karimpour-Razkenari、Maliheh Safavi、Mohammad Mahdavi、Mina Saeedi、Tahmineh Akbarzadeh

  DOI：10.2174/1570180815666180627121006

  日期：2019.6.27

  Background: This work reports design, synthesis, and in vitro cytotoxicity of novel coumarin-1,2,3-triazole-1,2,4-oxadiazole hybrids against three breast cancer cell lines MCF-7, MDA-MB-231, and T-47D. Methods: Synthetic procedure for the preparation of desired compounds was started from the reaction of coumarins or with propargyl bromide to give O-propargylated coumarins or 5. Then, click reaction

  背景：这项工作报告了新型香豆素-1,2,3-三唑-1,2,4-恶二唑杂种的设计，合成和体外细胞毒性对三种乳腺癌细胞MCF-7，MDA-MB-231和T-47D。 方法：从香豆素或与炔丙基溴反应生成O-炔丙基香豆素或5，开始合成所需化合物的过程。然后，在后面的化合物与3-芳基-5-（氯甲基）-1之间单击反应，2,4-恶二唑以良好的收率提供了所需的产物。 结果：在合成的化合物中，4-（（1-（（3-（4-氯苯基）-1,2,4-恶二唑-5-基）甲基）-1H-1,2,3-三唑-4- （yl）methoxy）-2H-chromen-2-one（9a）对乳腺癌细胞系表现出最佳的细胞毒性。 结论：化合物9a对MDA-MB-231和T-47D细胞的活性最高，而化合物8a和8c对MCF-7的活性最高。
• Synthesis and anti-protozoal activity of novel dihydropyrrolo[3,4-d][1,2,3]triazoles
  作者：Yaşar Dürüst、Hamza Karakuş、Marcel Kaiser、Deniz Tasdemir

  DOI：10.1016/j.ejmech.2011.12.028

  日期：2012.2

  containing heterocyclic compounds continue to gain interest in synthesis of chemical entities and exhibit various biological activities as anti-protozoal and anti-cancer agents. By using the principle of bioisosterism, a series of novel oxadiazolyl pyrrolo triazole diones; namely, (3aS,6aR)-1-((3-(4-substituted phenyl)-1,2,4-oxadiazol-5-yl)methyl)-5-phenyl-1,6a-dihydropyrrolo[3,4-d][1,2,3] triazole-4,6(3aH

  含1,2,4-恶二唑和1,2,3-三唑的杂环化合物继续引起化学实体合成的兴趣，并表现出各种作为抗原生动物和抗癌剂的生物学活性。利用生物立体异构原理，合成了一系列新型的恶二唑基吡咯并三唑二酮；即（3a S，6a R）-1-（（（3-（4-取代苯基）-1,2,4-恶二唑-5-基）甲基）-5-苯基-1,6a-二氢吡咯[3，通过新型5-叠氮基甲基3-的1,3-偶极环加成反应设计合成了4-d] [1,2,3]三唑-4,6（3a H，5 H）-二酮（5a - k）。芳基取代的1,2,4-恶二唑（4a – k）与N-苯基马来酰亚胺。通过光谱方法和物理特性阐明了所有环加合物的结构。的体外抗原生动物和这些新的杂环化合物的细胞毒活性进行了研究。
• Design, synthesis, antibacterial evaluation and molecular docking studies of novel pyrazole/1,2,4-oxadiazole conjugate ester derivatives
  作者：Navaneetha Depa、Harikrishna Erothu

  DOI：10.1007/s00044-021-02710-z

  日期：2021.5

  2,4-oxadiazole conjugate ester derivatives (7a–j) was synthesized. All the derivatives were evaluated for their in vitro antibacterial activity against Gram-positive (Enterococcus, Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Salmonella, Klebsiella and Escherichia coli) bacteria and their minimum inhibitory concentration (MIC) was determined. Some of the derivatives have shown significant

  由于全球抗菌素耐药性的快速增长，最需要开发新的抗菌素药物。因此，在这种情况下，合成了一系列新颖的吡唑/ 1,2,4-恶二唑共轭酯衍生物（7a–j）。评价所有衍生物对革兰氏阳性菌（肠球菌，枯草芽孢杆菌和金黄色葡萄球菌）和革兰氏阴性菌（沙门氏菌，克雷伯菌和大肠杆菌）的体外抗菌活性，并确定其最低抑菌浓度（MIC）。一些衍生物已显示出显着的生物学活性，其效力可与标准药物链霉素相媲美。。此外，通过计算机方法预测了分子对接研究，ADMET的药代动力学特性（吸收，分布，代谢，排泄和毒性），分子特性和TOPKAT分析。体外和计算机模拟研究表明，在所有化合物中，化合物（7a）已显示出显着的生物学活性，且LibDock得分为162.751 kcal / mol。所有合成的衍生物通过FTIR，1 H NMR，13 C NMR和质谱确认。