2-(2-氯苯基)-噻唑-4-羧酸乙酯 | 132089-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(2-氯苯基)-噻唑-4-羧酸乙酯
• 中文别名: 2-(2-氯苯基)噻唑-4-甲酸乙酯
• 英文名称: ethyl 2-(2-chlorophenyl)thiazole-4-carboxylate
• 英文别名: ethyl 2-(2-chlorophenyl)-4-thiazolecarboxylate；ethyl 2-(2-chlorophenyl)-1,3-thiazole-4-carboxylate
• CAS: 132089-36-2
• 化学式: C₁₂H₁₀ClNO₂S
• 分子量: 267.736
• InChiKey: FHKIJGQXQOGHAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934100090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(2-Chloro-phenyl)-thiazole-4-carboxylic acid ethyl ester
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-(2-Chloro-phenyl)-thiazole-4-carboxylic acid ethyl ester
CAS number: 132089-36-2

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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: C12H10ClNO2S
Molecular weight: 267.7

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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, 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：

  2-(2-氯苯基)-噻唑-4-羧酸乙酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 2-(2-chlorophenyl)-1,3-thiazole-4-carbohydrazide
  参考文献：
  名称：

  一些含有酰腙部分的新型苯基噻唑衍生物的设计、合成和抗真菌活性

  摘要：

  农作物真菌病害对全球农作物生产和质量构成严重威胁。开发新型高效杀菌剂是防治作物病害的重要措施。我们前期对天然产物噻孢菌素A的结构优化和生物活性研究发现，苯基噻唑是一种优异的抗真菌骨架。为了寻找新的杀菌剂，利用活性子结构原理设计合成了45种含有酰腙结构的苯基噻唑衍生物。拼接。除了化合物 E1、E14 和 E33 之外，45 种化合物中有 42 种是新化合物。它们的结构通过 1H NMR、13C NMR 和 HRMS 进行了结构表征。目标化合物在 25 μg/mL 浓度下对稻瘟病菌、山茶炭疽菌、玉米双极菌和核盘菌的抗真菌活性进行了评估。生物测定结果表明，大多数化合物在 25 μg/mL 浓度下对米霉和茶霉表现出优异的抗真菌活性。其中，化合物E4、E10、E14、E17、E23、E26和E27对米霉的抑制率超过80%，EC50值为1.66、2.01、2.26、1.45、1.50、1.29和2.65。

  DOI：

  10.3390/molecules28207084
• 作为产物：
  描述：

  2-氯苯甲酰胺 在 劳森试剂 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.0h， 生成 2-(2-氯苯基)-噻唑-4-羧酸乙酯
  参考文献：
  名称：

  作为 FFA2 激动剂的新型苯基噻唑-甲酰胺酸衍生物的合成、活性和对接研究

  摘要：

  游离脂肪酸受体 2 (FFA2)，也称为 GPR43，由短链脂肪酸 (SCFA) 激活，短链脂肪酸 (SCFA) 主要由肠道微生物群通过未消化的碳水化合物和膳食纤维的发酵产生。FFA2 目前似乎是肥胖、糖尿病、炎症性疾病和癌症管理的潜在目标。在这项研究中，合成了一系列新型苯基噻唑-甲酰胺酸衍生物，并将其作为潜在的正构 FFA2 配体用于结构-活性关系的研究。化合物6E被发现表现出稳定的hFFA2转染的CHO-K1细胞中的强效的双重激动活性（EC 50 = 23.1 μ米）作为阳性对照丙酸（EC 50= 43.3 μ米）。我们还报告了基于 hFFA1 以 2.3 Å 分辨率与 TAK-875 结合的晶体结构的诱变研究结果，以确定诱导 FFA2 激活的正构激动剂6e 的重要残基。

  DOI：

  10.1111/cbdd.12729

文献信息

• [EN] INHIBITORS OF HCV NS5B POLYMERASE<br/>[FR] INHIBITEURS DE LA POLYMERASE NS5B DU VHC
  申请人：UPJOHN CO

  公开号：WO2004002977A1

  公开（公告）日：2004-01-08

  The present invention porivdes compounds of Formula I, compositons and methods that are useful for treating viral infections and associated diseases, particularly HCV infections and associated diseases.

  本发明提供了式I化合物、组合物及方法，这些化合物、组合物及方法对于治疗病毒感染及相关疾病具有效用，特别是HCV感染及相关疾病。
• Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new oxadiazole and thiazole analogs
  作者：Mahmood-ul-Hassan Khan、Shahid Hameed、Tashfeen Akhtar、Najim A. Al-Masoudi、Wasfi A. Al-Masoudi、Peter G. Jones、Christophe Pannecouque

  DOI：10.1007/s00044-016-1669-9

  日期：2016.10

  A series of 2-adamantyl-5-arylthiazolyl-1,3,4-oxadiazoles 7a–x together with thiazoles 13 and 14 were synthesized. Compounds 7a–l, 13, and 14 were tested in vitro with the aim of identifying novel lead compounds active against human immunodeficiency virus type-1 and human immunodeficiency virus type-2 activity in MT-4 cells. Title compounds were also tested against representatives of Gram-positive

  合成了一系列2-金刚烷基-5-芳基噻唑基-1,3,4-恶二唑7a – x以及噻唑13和14。化合物7a中-升，13，和14在体外用的鉴定新的铅在MT-4细胞的化合物对人免疫缺陷病毒1型和人免疫缺陷病毒2型活性的活性的目的进行了测试。还测试了标题化合物对革兰氏阳性和革兰氏阴性细菌（金黄色葡萄球菌，沙门氏菌），各种分枝杆菌菌株（Fort分支杆菌和耻垢分枝杆菌（Mycobacterium smegmatis），酵母（白色念珠菌）和霉菌（Aspergillus fumigatus）。除了化合物13和14表现出抗人免疫缺陷病毒1活性（EC 50值为1.79和2.39μM，选择性指数分别为18和4）外，所有化合物均未显示出抗病毒或抗微生物活性。另一方面，化合物7a和7j对人CD4 +淋巴细胞（MT-4）显示出明显的细胞毒性。因此，评估了7a和7j对两种表现出IC的实体肿瘤衍生细胞系的抗增殖活性针对Hep-G2细胞系的50个值分别为8
• New Aryl-1,3-thiazole-4-carbohydrazides, Their 1,3,4-Oxadiazole-2- thione, 1,2,4-Triazole, Isatin-3-ylidene and Carboxamide Derivatives. Synthesis and Anti-HIV Activity
  作者：Mehwash Zia、Tashfeen Akhtar、Shahid Hameed、Najim A. Al-Masoudi

  DOI：10.5560/znb.2012-0095

  日期：2012.7.1

  A series of isatin-3-ylidene (6a-i) and arylthiazolyl-1,3,4-oxadiazole-2-thione derivatives 7a-i derived from arylthiazolyl carbohydrazide analogs 4a-i were synthesized. Analogously, coupling of 4f with various amino acid methyl esters in the presence of HOBt/DCC reagents afforded the carboxamide derivatives 9a-d. The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. All compounds are inactive, except compounds 9b and 9c which showed inhibition of HIV-1 with EC₅₀ = 2:34 μg mL^-1, and 1.12 μg mL^-1 with therapeutic indexes (SI) of 9 and <1, respectively.

  从芳基噻唑羧酰肼类似物 4a-i 合成了一系列异汀-3-亚基（6a-i）和芳基噻唑-1,3,4-恶二唑-2-硫酮衍生物 7a-i。同样，在 HOBt/DCC 试剂存在下，将 4f 与各种氨基酸甲酯偶联，可得到羧酰胺衍生物 9a-d。在 MT-4 细胞中对新合成的化合物进行了抗 HIV-1 和 HIV-2 检测。除了化合物 9b 和 9c 对 HIV-1 有抑制作用（EC50 = 2:34 μg mL-1 和 1.12 μg mL-1），治疗指数（SI）分别为 9 和 1 外，其他化合物均无活性。
• Steric and Electronic Factors Influence Regio-isomeric Thiazole Formations Between Substituted Benzothioamides and Ethyl Bromopyruvate
  作者：Jun Liang、Valerie Dorman Soucy、Vickie Tusi、Yanzhou Liu、Birong Zhang、Yingjie Lai、Steve Magnuson、Bingyan Zhu、Fangdao Wang、Jinghao Gu、Qingfen Zhang、Yuan Wu、Wei Deng、Wenqian Yang

  DOI：10.1002/jhet.1644

  日期：2014.7

  unexpected thiazole 1B formation when 2,6‐dichlorobenzothioamide 1 and ethyl bromopyruvate were reacted under basic conditions at elevated temperatures in ethanol. Thiazole 1B, regio‐isomeric to that expected under conventional Hantzsch conditions, was extensively characterized and later confirmed by single crystal X‐ray structure. We carried out this transformation with several substituted benzothioamides and

  我们观察到，在碱性条件下，在乙醇中升高的温度下，当2,6-二氯苯并硫代酰胺1与溴丙酮酸乙酯反应时，噻唑1B会意外地形成。噻唑1B与常规Hantzsch条件下预期的区域异构体具有广泛的特征，后来通过单晶X射线结构得到证实。我们用几种取代的苯并硫代酰胺进行了这种转化，发现意外的噻唑区域异构体的形成高度依赖于苯环上邻位取代基的空间位阻和电子特性。提出了一种机制来解释这种新颖的转变。
• Inhibitors of HCV NS5B polymerase
  申请人：Finzel Craig Barry

  公开号：US20060004063A1

  公开（公告）日：2006-01-05

  The present invention provides compounds of Formula I, compositions and methods that are useful for treating viral infections and associated diseases, particularly HCV infections and associated diseases.

  本发明提供了I式化合物、组合物和方法，用于治疗病毒感染和相关疾病，特别是HCV感染和相关疾病。