4-(3-氟苯基)-2-氨基噻唑 | 446065-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(3-氟苯基)-2-氨基噻唑
• 中文别名: 4-(3-氟-苯基)-噻唑-2-胺
• 英文名称: 4-(3-fluorophenyl)thiazol-2-amine
• 英文别名: 2-amino-4-(m-fluorophenyl)thiazole；4-(3-Fluorophenyl)-1,3-thiazol-2-amine
• CAS: 446065-20-9
• 化学式: C₉H₇FN₂S
• mdl: MFCD03094297
• 分子量: 194.232
• InChiKey: XBHHILITQUEDDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934100090
• 储存条件：
  存储条件：2-8°C，避光保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(3-Fluorophenyl)thiazol-2-ylamine
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: 4-(3-Fluorophenyl)thiazol-2-ylamine
CAS number: 446065-20-9

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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, 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: C9H7FN2S
Molecular weight: 194.2

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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, nitrogen oxides, hydrogen fluoride, sulfur oxides.

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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：

  4-(3-氟苯基)-2-氨基噻唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到5-bromo-4-(3-fluorophenyl)thiazol-2-amine
  参考文献：
  名称：

  一种取代的噻唑衍生物及其用途

  摘要：

  本发明提供通式(Ⅰ)所示化合物、或其立体异构体、药学可接受的盐、溶剂化物、水合物、化学保护的形式或前药，其具有抑制腺苷受体2a(A2a)的作用，可以作为腺苷受体2a(A2a)拮抗剂，用于治疗肿瘤，

  公开号：

  CN109293652B
• 作为产物：
  描述：

  3-氟苯乙烯 在 1,3-二溴-5,5-二甲基海因 、 水 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 4-(3-氟苯基)-2-氨基噻唑
  参考文献：
  名称：

  由1,3-二溴-5,5-二甲基乙内酰脲（DBH）介导的苯乙烯衍生物合成2-氨基噻唑

  摘要：

  据报道，通过DBH介导的苯乙烯和硫脲的氧化环化合成2-氨基噻唑的有效方法。使用DBH作为溴源和氧化剂，通过两步一锅法成功地将各种烯烃成功转化为相应的2-氨基噻唑，产率为10-81％。该方法可以容易地以克为单位进行，并且成功地用于以苯乙烯为起始原料的抗炎药fanetizole的合成。

  DOI：

  10.1016/j.tet.2018.05.021

文献信息

• Synthesis and biological evaluation of N-(4-phenylthiazol-2-yl)cinnamamide derivatives as novel potential anti-tumor agents
  作者：Yong Luo、Yongxia Zhu、Kai Ran、Zhihao Liu、Ningyu Wang、Qiang Feng、Jun Zeng、Lidan Zhang、Bing He、Tinghong Ye、Shirui Zhu、Xiaolong Qiu、Luoting Yu

  DOI：10.1039/c4md00573b

  日期：——

  In this study, a series of novel N-(4-phenylthiazol-2-yl)-cinnamamide derivatives (7a–8n) were synthesized and evaluated for their anti-proliferative activities in vitro.

  在这项研究中，合成了一系列新型的N-(4-苯基噻唑-2-基)-肉桂酰胺衍生物（7a–8n），并评估了它们在体外对细胞增殖的抑制活性。
• THERAPEUTIC COMPOUNDS AND RELATED METHODS OF USE
  申请人：Suzuki Masaki

  公开号：US20150307477A1

  公开（公告）日：2015-10-29

  Methods of treating disorders using compounds that modulate striatal-enriched tyrosine phosphatase (STEP) are described herein. Exemplary disorders include schizophrenia and cognitive deficit.

  本文描述了利用调节纹状体富集的酪氨酸磷酸酶（STEP）的化合物来治疗疾病的方法。示例疾病包括精神分裂症和认知缺陷。
• Identification of novel 2-aminothiazole conjugated nitrofuran as antitubercular and antibacterial agents
  作者：Kai Ran、Chao Gao、Hongxia Deng、Qian Lei、Xinyu You、Ningyu Wang、Yaojie Shi、Zhihao Liu、Wei Wei、Cuiting Peng、Lu Xiong、Kunjie Xiao、Luoting Yu

  DOI：10.1016/j.bmcl.2016.05.088

  日期：2016.8

  infections. In order to develop promising antitubercular and antibacterial lead compounds, we designed and synthesized a new series of derivatives of 2-aminothiazole conjugated nitrofuran with activities against both Mycobacterium tuberculosis and Staphylococcus aureus. Eight compounds 12e, 12k, 12l, 12m, 18a, 18d, 18e, and 18j emerged as promising antitubercular agents. Structure–activity relationships (SARs)

  抗生素抗性病原体的出现是细菌感染治疗中一个持续存在的主要问题。为了开发有前景的抗结核和抗菌先导化合物，我们设计并合成了一系列新的2-氨基噻唑共轭硝基呋喃衍生物，具有对抗结核分枝杆菌和金黄色葡萄球菌的活性。八个化合物12e，12k，12l，12m，18a，18d，18e和18j出现了有希望的抗结核药物。讨论了结构-活性关系（SARs），结果表明，在5-硝基-N-（4-苯基噻唑-2-基）呋喃-2-羧酰胺的苯位置3处取代的衍生物表现出优异的效能。最有效的化合物18e在该位置被苯甲酰胺取代，对Mtb H37Ra的最低抑菌浓度（MIC）为0.27μg / mL，对金黄色葡萄球菌的抑菌浓度为1.36μg/ mL 。此外，化合物18e对正常的Vero细胞没有明显的细胞毒性（IC 50 = 50.2μM）。结果表明，氨基噻唑共轭硝基呋喃的新型支架将是一类有前景的有效抗结核和抗菌药物。
• Synthesis, characterization and antimicrobial studies of a few novel thiazole derivatives
  作者：Aletti S. Praveen、Hemmige S. Yathirajan、Badiadka Narayana、Balladka K. Sarojini

  DOI：10.1007/s00044-013-0629-x

  日期：2014.1

  A series of novel N-[4-(substituted)-1,3-thiazol-2-yl]-2-(substituted)acetamide (9a–m) and methyl 2-(2-(2-(substituted)acetamido)thiazol-4-yl)acetate (9n–o) derivatives have been synthesized and compounds were characterised by spectral and analytical studies. All compounds were screened for their in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa

  一系列新颖的N- [4-（取代的）-1,3-噻唑-2-基] -2-（取代的）乙酰胺（9a – m）和甲基2-（2-（2-（取代的）乙酰胺基）已经合成了噻唑-4-基）乙酸酯（9n - o）衍生物，并通过光谱和分析研究对化合物进行了表征。所有化合物进行了筛选针对其体外抗菌活性的金黄色葡萄球菌，大肠杆菌，铜绿假单胞菌和肺炎克雷伯氏菌纸片扩散法和针对抗真菌活性马尔尼菲青霉，须发癣菌，曲霉属 黄曲霉和曲霉 曲霉通过连续平板稀释法。化合物9b，9e，9m和9o对所有测试的细菌菌株均表现出生长抑制作用，MIC值在12.5至6.25μg/ ml之间变化。在测试的抗真菌活性化合物中，9a，9b，9d，9j，9k，9p和9n表现出对所有测试菌株的广泛活性。大多数新合成的化合物对真菌菌株而非细菌菌株均有效。但是，有些化合物如9a，9e，9j，9k和9i对某些细菌菌株表现出选择性敏感性，而它们无法维持其他菌株的生长。
• 一种由苯乙烯类化合物合成1,3-取代噻唑环 类化合物的方法
  申请人：河南师范大学

  公开号：CN107501204B

  公开（公告）日：2020-03-06

  本发明公开了一种由苯乙烯类化合物合成1,3‑取代噻唑环类化合物的方法，属于噻唑环类衍生物的合成技术领域。本发明的技术方案要点为：一种由苯乙烯类化合物合成1,3‑取代噻唑环类化合物的方法，将苯乙烯类化合物和相转移催化剂溶于水中，再加入二溴海因DBH，于60℃反应，反应结束后旋干水并溶于有机溶剂中，再加入硫脲类化合物回流反应制得目标产物1,3‑取代噻唑环类化合物。本发明的合成方法产率较高、反应温和、成本低廉且环境友好。