4-(4-氟苯基)-5-甲基噻唑-2-胺 | 2928-00-9

• 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-(4-氟苯基)-5-甲基噻唑-2-胺
• 英文名称: 4-(4-fluorophenyl)-5-methylthiazol-2-amine
• 英文别名: 4-(4-fluorophenyl)-5-methyl-1,3-thiazole-2-amine；4-(4-Fluorophenyl)-5-methyl-1,3-thiazol-2-amine
• CAS: 2928-00-9
• 化学式: C₁₀H₉FN₂S
• mdl: MFCD02663854
• 分子量: 208.259
• InChiKey: KPOAMSWZRRKBHN-UHFFFAOYSA-N

物化性质

• 熔点：
  127 °C
• 沸点：
  346.5±27.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934100090
• WGK Germany：
  3

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-(4-Fluorophenyl)-5-methyl-1,3-thiazol-2-amine
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-(4-Fluorophenyl)-5-methyl-1,3-thiazol-2-amine
CAS number: 2928-00-9

---

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.
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: C10H9FN2S
Molecular weight: 208.3

---

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.

---

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：

  4-(4-氟苯基)-5-甲基噻唑-2-胺 在 potassium fluoride 、 tetrafluoroboric acid 、 silica gel 、 sodium nitrite 作用下， 生成 2-fluoro-5-methyl-4-(p-fluorophenyl)-thiazole
  参考文献：
  名称：

  Gruenert,C. et al., Zeitschrift fur Chemie, 1970, vol. 10, p. 116

  摘要：

  DOI：
• 作为产物：
  描述：

  4'-氟苯丙酮 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 4-(4-氟苯基)-5-甲基噻唑-2-胺
  参考文献：
  名称：

  Synthesis and biological evaluation of novel thiazole- VX-809 hybrid derivatives as F508del correctors by QSAR-based filtering tools

  摘要：

  The most common CF mutation, F508del, impairs the processing and gating of CFTR protein. This deletion results in the improper folding of the protein and its degradation before it reaches the plasma membrane of epithelial cells. Present correctors, like VX809 only induce a partial rescue of the mutant protein. Our previous studies reported a class of compounds, called aminoarylthiazoles (AATs), featuring an interesting activity as correctors. Some of them show additive effect with VX809 indicating a different mechanism of action. In an attempt to construct more interesting molecules, it was thought to generate chemically hybrid compounds, blending a portion of VX809 merged to the thiazole scaffold. This approach was guided by the development of QSAR analyses, which were performed based on the F508del correctors so far disclosed in the literature. This strategy was aimed at exploring the key requirements turning in the corrector ability of the collected derivatives and allowed us to derive a predictive model guiding for the synthesis of novel hybrids as promising correctors. The new molecules were tested in functional and biochemical assays on bronchial CFBE41o-cells expressing F508del-CFTR showing a promising corrector activity. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.12.030

文献信息

• Diacylglycerol Acyltransferase Inhibitors
  申请人：Bolin David Robert

  公开号：US20100113782A1

  公开（公告）日：2010-05-06

  Provided herein are compounds of the formula (I): were R1 is phenyl, R2 is hydrogen, halogen or lower alkyl, X is carbon on nitrogen, and R3 is isoquinoline, -amino, or a 4- to 6-membered heterocycloalkyl ring and pharmaceutically acceptable salts thereof, which are active as DGAT inhibitors and therefore find uses in treatment of diseases associated with abnormal metabolism of triglicerides such as, for example, obesity, type II diabetes mellitus and metabolic syndrome.

  本文提供了化合物的公式（I）：其中R1为苯基，R2为氢、卤素或低碳烷基，X为碳或氮，R3为异喹啉基、氨基或含有4至6个成员的杂环烷基环，并且其药学上可接受的盐，这些化合物作为DGAT抑制剂具有活性，因此可用于治疗与三酸甘油酯异常代谢相关的疾病，例如肥胖症、2型糖尿病和代谢综合征。
• Synthesis and Antimicrobial Activities of Some Novel 2,3-Substituted-1,3-Thiazolidin-4-ones Derived from 2-Amino-1,3-thiazole
  作者：K. Maher

  DOI：10.14233/ajchem.2017.20925

  日期：——

  New 2,3-substituted-1,3-thiazolidin-4-one (6a-f) were prepared by cyclocondensation of 2-[6-(4-chlorobenzyloxy)-2-naphthyliden]-4-(4-substituted phenyl)-5-methyl-1,3-thiazole (5a-f) and mercaptoacetic acid in benzene. The synthesized compounds were characterized on the basis of elemental analysis, 1H NMR, 13C NMR and FT-IR. The prepared compounds have been screened in vitro against two Gram-positive Staphylococcus aureus, Staphylococcus epidermidis, and two Gram-negative Escherichia coli, Pseudomonas aernuginosa for antibacterial activity and two fungal strains Candida albicans, Candida krusei for antifungal activity using ciprofloxacin, ampicillin and ketoconazole with minimal inhibitory concentration (MIC) value of 10 mcg/L in DMSO. Compounds 6a and 6d showed good antibacterial and antifungal activities compared to reference medications utilized within this study.

  新型2,3取代的1,3-噻唑烷-4-酮（6a-f）是通过将2-[6-(4-氯苄氧)-2-萘烯]-4-(4-取代苯基)-5-甲基-1,3-噻唑（5a-f）与巯基乙酸在苯中缩合制备的。合成的化合物通过元素分析、1H NMR、13C NMR和FT-IR进行表征。所制备的化合物在体外针对两种革兰阳性菌金黄色葡萄球菌、表皮葡萄球菌和两种革兰阴性菌大肠杆菌、铜绿假单胞菌进行抗菌活性筛选，以及针对两种真菌菌株白色念珠菌、克鲁斯氏念珠菌进行抗真菌活性评估，使用环丙沙星、氨苄青霉素和酮康唑，最低抑菌浓度（MIC）值为10 mcg/L在DMSO中。化合物6a和6d相较于本研究中使用的参考药物显示出良好的抗菌和抗真菌活性。
• Sequencing Groebke–Blackburn–Bienaymé and Aza-Michael Addition Reactions: A Modular Strategy for Accessing a Diverse Collection of Constrained Benzoxazepine and Imidazopyrazine Systems
  作者：Taleb H. Al-Tel、Vunnam Srinivasulu、Farah Al-Marzooq、Mohamad Hamad、Monther A. Khanfar、Mani Ramanathan、Nelson C. Soares

  DOI：10.1055/s-0040-1706006

  日期：2021.6

  permits access to diversely functionalized benzoxazepinium scaffolds fused to various heterocycles. The described strategy features a one-pot combination of the Groebke–Blackburn–Bienaymé reaction and an aza-Michael addition. Methyl (E)-4-(2-formylphenoxy)but-2-enoate and its derivatives are utilized as central elements in this cascade. These building blocks are reacted with a variety of functionalized

  我们提出了一种不同的策略，允许访问融合到各种杂环的功能不同的苯并a庚因支架。所描述的策略具有Groebke–Blackburn–Bienaymé反应与aza-Michael加成反应的一锅法组合。（E）-4-（2-甲酰基苯氧基）丁-2-烯酸酯及其衍生物被用作该级联反应的中心元素。在三氟with酸[[Yb（OTf）3 ]催化下，这些结构单元与各种官能化的氨基嗪和叔丁基异氰化物反应。随后的级联反应代表了快速，模块化和原子经济的过程，该过程导致了从广泛的底物范围构建受约束的苯并氧杂pin鎓体系的各种集合。
• Modification and Biological Evaluation of Thiazole Derivatives as Novel Inhibitors of Metastatic Cancer Cell Migration and Invasion
  作者：Shilong Zheng、Qiu Zhong、Yulan Xi、Madhusoodanan Mottamal、Qiang Zhang、Richard L. Schroeder、Jayalakshmi Sridhar、Ling He、Harris McFerrin、Guangdi Wang

  DOI：10.1021/jm500724x

  日期：2014.8.14

  emerged as a potential therapeutic target, as its expression in cancer cells is closely associated with tumor progression and metastasis. Following the initial discovery of a series of thiazole derivatives that demonstrated potent antimigration and antiinvasion activities via possible inhibition of fascin function, we report here the design and synthesis of 63 new thiazole derivatives by further structural

  Fascin 最近已成为潜在的治疗靶点，因为它在癌细胞中的表达与肿瘤进展和转移密切相关。在最初发现一系列通过可能抑制肌成束蛋白功能而表现出有效抗迁移和抗侵袭活性的噻唑衍生物之后，我们在此报告了 63 种新型噻唑衍生物的设计和合成，通过进一步的结构修饰来寻找更有效的肌成束蛋白抑制剂。在噻唑氮上具有更长烷基链取代的5系列类似物比具有其他结构基序的类似物表现出更大的抗迁移活性。最强大的模拟，5p，在 24 nM 时抑制了 50% 的细胞迁移。此外，噻唑类似物显示出很强的抗血管生成活性，在鸡胚胎膜试验中阻断了新血管的形成。最后，进行了一项功能研究，以通过与 F-肌动蛋白捆绑蛋白肌成束蛋白的相互作用来研究作用机制。
• Imidazole Derivatives as Promising Agents for the Treatment of Chagas Disease
  作者：Julianna Siciliano de Araújo、Alfonso García-Rubia、Victor Sebastián-Pérez、Titilola D. Kalejaiye、Patrícia Bernardino da Silva、Cristina Rosa Fonseca-Berzal、Louis Maes、Harry P. De Koning、Maria de Nazaré Correia Soeiro、Carmen Gil

  DOI：10.1128/aac.02156-18

  日期：2019.4

  parasite Trypanosoma cruzi, is no longer just a problem for the American continents but has become a global health threat. Current therapies, i.e., nifurtimox and benznidazole (Bz), are far from being adequate, due to their undesirable effects and their lack of efficacy in the chronic phases of the disease. In this work, we present an in-depth phenotypic evaluation in T. cruzi of a new class of imidazole compounds

  南美锥虫病在首次被描述后已有100多年的历史，在21个拉丁美洲国家仍是地方病，并已传播到其他大洲。实际上，这种由原生动物寄生虫克氏锥虫引起的疾病已不再只是美洲大陆的问题，而是已成为全球健康威胁。由于其不良作用以及在疾病的慢性期中缺乏功效，目前的疗法，即硝呋替莫和苯并硝唑（Bz），远远不够。在这项工作中，我们提出了一种新的咪唑类化合物在克鲁氏锥虫中的深入表型评估，该咪唑化合物是在先前针对不同锥虫的表型筛选中发现的，被设计为潜在的cAMP磷酸二酯酶（PDE）抑制剂。证实了几种与Bz相似或优于Bz的活性，从而促进了命中优化和扩展的结构活性关系的合成程序，旨在改善类似药物的性质，例如水溶性，从而产生了抑制浓度为50％的额外命中（IC50）值与Bz相似。进一步研究了一种具有代表性的命中化合物9对血锥虫的细胞作用。透射电子显微镜显示，在与IC50浓度温育仅2小时后，细胞变化与诱导的自噬和渗透压一致，这