2-(4-溴苯基)-5-(氯甲基)-1,3,4-恶二唑 | 568544-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-溴苯基)-5-(氯甲基)-1,3,4-恶二唑
• 英文名称: 2-(4-bromophenyl)-5-(chloromethyl)-1,3,4-oxadiazole
• 英文别名: 2-(chloromethyl)-5-(4-bromophenyl)-1,3,4-oxadiazole
• CAS: 568544-04-7
• 化学式: C₉H₆BrClN₂O
• mdl: MFCD03273472
• 分子量: 273.516
• InChiKey: JJZRXTXSRJLBRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

---

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

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-(4-Bromophenyl)-5-(chloromethyl)-1,3,4-oxadiazole
CAS number: 568544-04-7

---

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.

---

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.

---

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.

---

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:

---

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.

---

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

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(4-溴苯基)-5-(氯甲基)-1,3,4-恶二唑 在 sodium azide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以78%的产率得到2-(azidomethyl)-5-(4-bromophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  从可用的氯甲基-1,3,4 / 1,2开始，一锅CuAAC合成（1H-1,2,3-三唑-1-基）甲基-1,3,4 / 1,2,4-恶二唑， 4-恶二唑

  摘要：

  一锅法CuAAC合成（1 H -1,2,3-三唑-1基）甲基-1,3,4-恶二唑和（1 H -1,2,3-三唑-1基）甲基研究了通过与叠氮化物的随后亲核取代氯反应的三组分反应制得的1,2,4-恶二唑衍生物，以及在CuI存在下与炔烃进行的进一步“点击”反应。探索了新合成的2-（叠氮甲基）-1,3,4 / 1,2,4-恶二唑和氯甲基-1,3,4 / 1,2,4-恶二唑衍生物的效用，并确定了它们的局限性。新型5-（[[4-芳基-1 H -1,2,3-三唑-1-基]甲基] -3-（芳基）-1,2,4-恶二唑，2-（[4-芳基-1以高收率获得了H -1,2,3-三唑-1-甲基] -5-（芳基）-1,3,4-恶二唑。

  DOI：

  10.1002/jhet.4008
• 作为产物：
  描述：

  对溴苯甲酰肼 在 三氯氧磷 作用下， 以 乙酸乙酯 为溶剂， 生成 2-(4-溴苯基)-5-(氯甲基)-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 Antimicrobial Evaluation of Aminoguanidine and 3-amino- 1,2,4-triazole Derivatives as Potential Antibacterial Agents
  作者：Tian-Yi Zhang、Chao Li、Ya-Ru Li、Xiao-Zhen Li、Liang-Peng Sun、Chang-Ji Zheng、Hu-Ri Piao

  DOI：10.2174/1570180813666160819151239

  日期：2016.10.31

  A series of aminoguanidine derivatives bearing a 1,3,4-oxadiazole or piperazine moiety has been synthesized and fully characterized together with a series of 3-amino-1,2,4-triazole derivatives, and the resulting compounds were evaluated for their anti-bacterial activity. Most of these compounds showed broad-spectrum antibacterial activities against both Gram-positive and Gram-negative bacteria with

  已合成了一系列带有1,3,4-恶二唑或哌嗪部分的氨基胍衍生物，并与一系列3-氨基-1,2,4-三唑衍生物一起进行了全面表征，并评估了所得化合物的抗-细菌活性。这些化合物大多数对革兰氏阳性和革兰氏阴性细菌均具有广谱抗菌活性，其最低抑菌浓度（MIC）和最低杀菌浓度（MBC）值在1–64μg/ mL范围内，包括耐多药临床分离株和真菌。值得注意的是，化合物19e和19f的抗甲氧西林金黄色葡萄球菌（3167和3506）和喹诺酮抗S的活性高于加替沙星和莫西沙星。金黄色葡萄球菌（3505和3519）的MIC和MBC值在1-2 µg / mL范围内。这两种化合物还显示出显着的抗真菌活性，对白色念珠菌7535的MIC值为1μg/ mL，相当于标准药物氟康唑的MIC值。因此，这些结果表明，不含哌嗪部分的氨基胍衍生物是开发新型抗菌剂的令人感兴趣的支架。
• [EN] MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS<br/>[FR] DÉRIVÉS DE MANNOSE POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：VERTEX PHARMA

  公开号：WO2013134415A1

  公开（公告）日：2013-09-12

  The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula I: The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

  本发明涉及用于治疗或预防细菌感染的化合物。这些化合物的公式为I：。发明还提供了包含这些化合物的药用可接受组合物，以及使用组合物治疗细菌感染的方法。最后，发明提供了制造本发明化合物的方法。
• 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
• Synthesis and cytotoxicity of hybrids of 1,3,4- or 1,2,5-oxadiazoles tethered from ursane and lupane core with 1,2,3-triazole
  作者：Sergey A. Popov、Marya D. Semenova、Dmitry S. Baev、Tatiana S. Frolova、Michael A. Shestopalov、Chengzhang Wang、Zhiwen Qi、Elvira E. Shults、Māris Turks

  DOI：10.1016/j.steroids.2020.108698

  日期：2020.10

  linked to C-28 position of triterpene backbone demonstrated marked cytotoxic activity towards MCF-7 and HepG2 cells. The most active ester of ursolic acid with (1-((4-methyl-2-oxido-1,2,5-oxadiazol-3-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl substituent and 3-O-acetyl group was superior in activity and selectivity over doxorubicin and ursolic acid on MCF-7 cells. The length of the carbon spacer group may be

  Ursane 和 lupane 型（1-（（5-芳基-1,3,4-恶二唑-2-基）甲基）-1H-1,2,3-三唑-4-基）甲基和（1-（（4 -methyl-2-oxido-1,2,5-oxadiazol-3-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl 杂化物是通过 1,3-环加成反应制备的 唑-衍生的叠氮化物具有连接到三萜核心的 C-3 和 C-28 位的炔酯，并测试了细胞毒性。1,3,4-恶二唑的杂合化合物连接在三萜骨架的 3-和 28- 位上通过三唑间隔基和 1,2,5-恶二唑或 1,3,4-恶二唑的组合，与琥珀酸酯接头和 1,2 相连， 3-三唑在乌苏烷骨架的位置3-，是相对于所有测试的癌细胞不活动的。最终，呋喃烷片段和连接到三萜骨架 C-28 位置的 1,2,3-三唑的组合显示出对 MCF-7 和 HepG2 细胞的显着细胞毒活性。熊果酸与 (
• Design, synthesis, evaluation, and molecular docking of ursolic acid derivatives containing a nitrogen heterocycle as anti-inflammatory agents
  作者：Zhi-Yu Wei、Ke-Qiang Chi、Ke-Si Wang、Jie Wu、Li-Ping Liu、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2018.04.021

  日期：2018.6

  Ursolic acid derivatives containing oxadiazole, triazolone, and piperazine moieties were synthesized in an attempt to develop potent anti-inflammatory agents. Structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, and HRMS. Most of the synthesized compounds showed pronounced anti-inflammatory effects at 100 mg/kg. In particular, compound 11b, which displayed the most potent anti-inflammatory

  为了开发有效的消炎药，合成了含有恶二唑，三唑酮和哌嗪部分的熊草酸衍生物。通过1 H NMR，13 C NMR和HRMS阐明了合成化合物的结构。大多数合成的化合物在100 mg / kg时显示出明显的抗炎作用。特别地，显示出所有制备的化合物中最有效的抗炎活性的化合物11b，在腹膜内给药后具有69.76％的抑制作用，比参考药物吲哚美辛和布洛芬更有效。还通过3-（4,5-二甲基-2-噻唑基）-2,5-二苯基-2- H评估了化合物的细胞毒性。-溴化四氮唑（MTT）分析，没有化合物显示任何可观的细胞毒活性（IC 50 > 100μmol/ L）。此外，进行了合成化合物的分子对接研究以合理化所获得的生物学结果。总体而言，结果表明化合物11b可以是用于治疗炎症的治疗候选物。