2-对甲苯噻唑-4-羧酸乙酯 | 132089-32-8

• 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-对甲苯噻唑-4-羧酸乙酯
• 中文别名: 2-(4-甲基苯基)噻唑-4-羧酸乙酯
• 英文名称: ethyl 2-(p-tolyl)thiazole-4-carboxylate
• 英文别名: Ethyl 2-(4-methylphenyl)-1,3-thiazole-4-carboxylate
• CAS: 132089-32-8
• 化学式: C₁₃H₁₃NO₂S
• mdl: MFCD01935979
• 分子量: 247.318
• InChiKey: YJADELKTGPHXGE-UHFFFAOYSA-N

物化性质

• 熔点：
  45-46°C
• 沸点：
  375.9±44.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934100090
• 危险类别：
  IRRITANT
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-p-Tolyl-thiazole-4-carboxylic acid ethyl ester
Product Name:
Synonyms: 2-(4-Methylphenyl)-thiazole-4-carboxylic acid ethyl ester

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-p-Tolyl-thiazole-4-carboxylic acid ethyl ester
Ingredient name:
CAS number: 132089-32-8

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels, refrigerated.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C13H13NO2S
Molecular weight: 247.3

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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, 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-对甲苯噻唑-4-羧酸乙酯 在 氢氧化钾 作用下， 生成 2-(4-甲基苯基)-1,3-噻唑-4-羧酸
  参考文献：
  名称：

  A catch-and-release strategy for the combinatorial synthesis of 4-acylamino-1,3-thiazoles as potential CDK5 inhibitors

  摘要：

  Two-dimensional libraries of 4-acylamino-1,3-thiazoles 9 were prepared via Curtius rearrangement of 1,3-thiazole-4-carbonyl azides 6, trapping of the intermediate isocyanates with oxime resin, and thermal regeneration of the isocyanates from the washed resin in the presence of nucleophiles. Several compounds proved to be selective inhibitors of CDK5/p25 versus the closely homologous CDK2/cyclin A enzyme, with the best analogue (43) possessing over 100-fold selectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00726-1
• 作为产物：
  描述：

  丙酮酸乙酯 在 溴 、 sodium carbonate 作用下， 以 neat (no solvent) 为溶剂， 生成 2-对甲苯噻唑-4-羧酸乙酯
  参考文献：
  名称：

  无溶剂合成bacillamide类似物作为新型细胞毒性和抗炎药

  摘要：

  bacillamide（一种海洋来源的生物活性类胰蛋白酶生物碱）的十四种类似物的合成已通过高效的收敛途径完成。本无溶剂方案涉及在初始步骤中形成噻唑环，然后在2-羟基-4,6存在下，取代的2-烷基/芳基/杂芳基/氨基/氨基芳基噻唑-4-羧酸乙酯与色胺之间进行酰胺偶联。 -二甲基嘧啶，一种固相催化剂，可产生N- [2-（1 H-吲哚-3-基）乙基] -2-烷基/芳基/杂芳基/氨基/氨基芳基噻唑-4-羧酰胺作为bacillamide类似物，在噻唑环的2位具有结构变化。使用比色细胞增殖测定法评估了巴西酰胺及其类似物对三种癌细胞系（HCT-116，MDA-MD-231和JURKAT细胞系）的细胞毒活性。化合物17a和17b对这些细胞系表现出有效的抗细胞增殖活性，IC 50值分别在〜3.0μM和〜0.1-0.6μM范围内。初步的作用机制研究表明，这些化合物可启动caspase依赖性细胞凋亡。另外，化合物16d，16f，17a和17d

  DOI：

  10.1016/j.ejmech.2016.07.033

文献信息

• [EN] INHIBITORS OF HUMAN ATGL<br/>[FR] INHIBITEURS DE L'ATGL HUMAIN
  申请人：KARL FRANZENS UNIV GRAZ

  公开号：WO2021019051A1

  公开（公告）日：2021-02-04

  The present invention relates to novel inhibitors of adipose triglyceride lipase (ATGL) having an improved inhibitory activity against human ATGL (hATGL) as well as pharmaceutical compositions comprising these inhibitors, and their therapeutic use, particularly in the treatment or prevention of a lipid metabolism disorder, including, e.g., obesity, non-alcoholic fatty liver disease, type 2 diabetes, insulin resistance, glucose intolerance, hypertriglyceridemia, metabolic syndrome, cardiac and skeletal muscle steatosis, congenital generalized lipodystrophy, familial partial lipodystrophy, acquired lipodystrophy syndrome, atherosclerosis, or heart failure.

  本发明涉及新型抑制脂肪甘油三酯脂肪酶（ATGL）的抑制剂，其对人类ATGL（hATGL）具有改善的抑制活性，以及包含这些抑制剂的药物组合物，及其治疗用途，特别是在治疗或预防脂质代谢紊乱方面的用途，包括例如肥胖、非酒精性脂肪肝病、2型糖尿病、胰岛素抵抗、葡萄糖不耐症、高甘油三酯血症、代谢综合征、心脏和骨骼肌脂肪变性、先天性全身性脂肪营养不良、家族性部分脂肪营养不良、获得性脂肪营养不良综合征、动脉粥样硬化或心力衰竭。
• Design, synthesis and biological evaluation of novel thiazole-derivatives as mitochondrial targeting inhibitors of cancer cells
  作者：Xin Dang、Shuwen Lei、Shuhua Luo、Yixin Hu、Juntao Wang、Dongdong Zhang、Dan Lu、Faqin Jiang、Lei Fu

  DOI：10.1016/j.bioorg.2021.105015

  日期：2021.9

  production assay to assess the selected compounds inhibitory effect on HeLa cells energy production. The results displayed the test compounds significantly restrained ATP production of cancer cells. Overall, we have designed and synthesized a series of compounds which exhibited significant cytotoxicity against cancer cells and effectively inhibited mitochondrial energy production.

  线粒体是细胞维持必要代谢活动的关键能量生产来源。针对功能失调的线粒体特征一直是线粒体相关疾病研究的热点。对癌性线粒体代谢的研究是肿瘤治疗中持续关注的问题。在此，我们基于我们早期对线粒体靶向剂的研究，着手评估新型 TPP-噻唑衍生物家族的抗癌活性。具体而言，我们设计并合成了一系列 TPP-噻唑衍生物，并通过 MTT 测定显示大多数合成的化合物有效抑制了三种癌细胞系（HeLa、PC3 和 MCF-7）。在结构修改后，我们探索了 SAR 关系并确定了最有希望的化合物R13（IC50 of 5.52 μM) 用于进一步研究。同时，我们进行了 ATP 产生测定以评估所选化合物对 HeLa 细胞能量产生的抑制作用。结果显示测试化合物显着抑制癌细胞的ATP产生。总体而言，我们设计并合成了一系列对癌细胞具有显着细胞毒性并有效抑制线粒体能量产生的化合物。
• 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
• Powerful Antibacterial Activity of Phenyl‐Thiolatobismuth(III) Complexes Derived from Oxadiazolethiones
  作者：Ahmad Luqman、Victoria L. Blair、Rajini Brammananth、Paul K. Crellin、Ross L. Coppel、Philip C. Andrews

  DOI：10.1002/ejic.201500795

  日期：2015.10

  all bismuth(III) complexes were highly effective against all the bacteria, as demonstrated by very low MIC values (1.1–2.1 μM). Complexes BiPh(Me-PTOT)2 6, BiPh(Cl-PTOT)2 10 and BiPh(Br-PTOT)2 11, showed best activity against the multi-drug resistant bacteria VRE and MRSA with an MIC value of 1.0 μM. All these complexes and their corresponding thiones failed to show any prominent activity against M.

  七种新型 5-取代苯基噻唑恶二唑硫酮：[Me-PTOT(H)]、[MeO-PTOT(H)]、[MeS-PTOT(H)]、[F-PTOT(H)]、[Cl-PTOT(H) )]、[Br-PTOT(H)]和[CF3-PTOT(H)]，其中X-PTOT(H) = 5-[2-(4-X)噻唑-4-基]-1， 3,4-oxadiazole-2(3H)-thione, 4-X = C6H4}，是由它们相应的硫代酰胺合成的。来自这七种杂配硫醇铋配合物：BiPh(Me-PTOT)2 6, BiPh(MeO-PTOT)2 7, BiPh(MeS-PTOT)2 8, BiPh(F-PTOT)2 9, BiPh(Cl-PTOT)2 10、BiPh(Br-PTOT)2 11 和BiPh(CF3-PTOT)2 12 被合成和表征。复合物 [10(DMSO)2] 和 [11(DMSO)2] 的结构特征使用 X 射线衍射。硫酮及其
• 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。