2-(2-噻吩基)-1,3-噻唑-4-羧酸 | 24044-07-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 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-噻吩基)-1,3-噻唑-4-羧酸
• 中文别名: 2-(2-噻吩基)噻唑-4-羧酸
• 英文名称: 2-thiophen-2-yl-thiazole-4-carboxylic acid
• 英文别名: 2-(2-thienyl)-1,3-thiazole-4-carboxylic acid；2-(2-Thienyl)-thiazol-4-carbonsaeure；2-(Thiophen-2-yl)thiazole-4-carboxylic acid；2-thiophen-2-yl-1,3-thiazole-4-carboxylic acid
• CAS: 24044-07-3
• 化学式: C₈H₅NO₂S₂
• mdl: MFCD01936014
• 分子量: 211.265
• InChiKey: FGKCNTGJZXHKFJ-UHFFFAOYSA-N

物化性质

• 熔点：
  157 °C
• 沸点：
  441.5±43.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  >31.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 储存条件：
  | 室温 |

SDS

Name:	2-(2-Thienyl)-1 3-thiazole-4-carboxylic acid 97% Material Safety Data Sheet
Synonym:
CAS:	24044-07-3

Section 1 - Chemical Product MSDS Name:2-(2-Thienyl)-1 3-thiazole-4-carboxylic acid 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
24044-07-3	2-(2-Thienyl)-1,3-thiazole-4-carboxyli	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 24044-07-3: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 156 - 160 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H5NO2S2
Molecular Weight: 211

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, reducing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 24044-07-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-(2-Thienyl)-1,3-thiazole-4-carboxylic acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 24044-07-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 24044-07-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 24044-07-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(2-噻吩基)-1,3-噻唑-4-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2-噻吩基)-1,3-噻唑-4-羰酰氯
  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：

  2-噻吩-2-基-噻唑-4,5-二羧酸 反应 0.5h， 生成 2-(2-噻吩基)-1,3-噻唑-4-羧酸
  参考文献：
  名称：

  Robba; Le Guen, Bulletin de la Societe Chimique de France, 1969, vol. 5, p. 1762 - 1768

  摘要：

  DOI：

文献信息

• A Fragment-Based Method to Discover Irreversible Covalent Inhibitors of Cysteine Proteases
  作者：Stefan G. Kathman、Ziyang Xu、Alexander V. Statsyuk

  DOI：10.1021/jm500345q

  日期：2014.6.12

  reported which irreversibly tethers drug-like fragments to catalytic cysteines. We attached an electrophile to 100 fragments without significant alterations in the reactivity of the electrophile. A mass spectrometry assay discovered three nonpeptidic inhibitors of the cysteine protease papain. The identified compounds display the characteristics of irreversible inhibitors. The irreversible tethering system

  报道了一种新的基于片段的药物发现方法，该方法不可逆地将类药物片段束缚在催化半胱氨酸上。我们将亲电试剂连接到 100 个片段上，而亲电试剂的反应性没有显着改变。质谱分析发现了半胱氨酸蛋白酶木瓜蛋白酶的三种非肽抑制剂。鉴定出的化合物显示出不可逆抑制剂的特征。不可逆的束缚系统也显示出特异性：三种鉴定出的木瓜蛋白酶抑制剂不与 UbcH7、USP08 或带有 GST 标签的人类鼻病毒 3C 蛋白酶共价反应。
• Selective Inhibition of DNA Polymerase β by a Covalent Inhibitor
  作者：Shelby C. Yuhas、Daniel J. Laverty、Huijin Lee、Ananya Majumdar、Marc M. Greenberg

  DOI：10.1021/jacs.1c02453

  日期：2021.6.2

  has been closely linked to cancer. Selective inhibitors of this enzyme are lacking. Inspired by DNA lesions produced by antitumor agents that inactivate Pol β, we have undertaken the development of covalent small-molecule inhibitors of this enzyme. Using a two-stage process involving chemically synthesized libraries, we identified a potent irreversible inhibitor (14) of Pol β (KI = 1.8 ± 0.45 μM, kinact

  DNA 聚合酶 β (Pol β) 在 DNA 修复中起着至关重要的作用，并且与癌症密切相关。缺乏这种酶的选择性抑制剂。受使 Pol β 失活的抗肿瘤剂产生的 DNA 损伤的启发，我们着手开发这种酶的共价小分子抑制剂。使用涉及化学合成文库的两阶段过程，我们确定了Pol β的有效不可逆抑制剂 ( 14 ) ( K I = 1.8 ± 0.45 μM, k inact = (7.0 ± 1.0) × 10 –3 s –1 )。抑制剂14比其他 DNA 聚合酶选择性地灭活 Pol β。用14处理的 Pol β 胰蛋白酶消化物的 LC-MS/MS 分析鉴定了聚合酶结合位点内共价修饰的两个赖氨酸，其中一个先前被确定在DNA结合中起作用。荧光各向异性实验表明，用14预处理 Pol β可防止 DNA 结合。在野生型小鼠胚胎成纤维细胞 (MEF) 中使用前抑制剂 ( pro - 14 ) 的实验表明，抑制剂
• [DE] SUBSTITUIERTE 5, 6, 7, 8-TETRAHYDRO-PYRIDO[4, 3-d]PYRIMIDIN-2-YL- UND 5, 6, 7, 8-TETRAHYDRO-CHINAZOLIN-2-YL-VERBINDUNGEN<br/>[EN] SUBSTITUTED 5, 6, 7, 8-TETRAHYDRO-PYRIDO[4, 3-D]PYRIMIDINE-2-YL COMPOUNDS AND 5, 6, 7, 8-TETRAHYDRO-QUINAZOLINE-2-YL COMPOUNDS<br/>[FR] COMPOSES DE 5, 6, 7, 8-TETRAHYDRO-PYRIDO[4, 3-D]PYRIMIDINE-2-YL ET DE 5, 6, 7, 8-TETRAHYDRO-QUINAZOLINE-2-YL SUBSTITUEES
  申请人：GRUENENTHAL GMBH

  公开号：WO2005105759A1

  公开（公告）日：2005-11-10

  Die vorliegende Erfindung betrifft substituierte 5,6,7,8-Tetrahydro-pyrido[4,3-­d]pyrimidin-2-yl- und 5,6,7,8-Tetrahydro-chinazolin-2-yl-Verbindungen, Verfahren zu ihrer Herstellung, Arzneimittel enthaltend diese Verbindungen sowie deren Verwendung zur Herstellung von Arzneimitteln.

  这项发明涉及取代的5,6,7,8-四氢-吡啶并[4,3-d]嘧啶-2-基和5,6,7,8-四氢-喹唑啉-2-基化合物，其制备方法，含有这些化合物的药物以及它们用于制备药物的用途。
• Substituted 5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2-yl compounds and 5,6,7,8-tetrahydroquinazoline-2-yl compounds
  申请人：Oberboersch Stefan

  公开号：US20070249631A1

  公开（公告）日：2007-10-25

  Substituted 5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl and 5,6,7,8-tetrahydro-quinazolin-2-yl compounds, corresponding to formula I processes for the production thereof, pharmaceutical preparations containing these compounds the use thereof for the production of pharmaceutical preparations and related method of treating or inhibiting certain disorders or conditions, including pain.

  将5,6,7,8-四氢吡啶并[4,3-d]嘧啶-2-基和5,6,7,8-四氢喹唑啉-2-基化合物替代为公式I，生产这些化合物的方法，含有这些化合物的药物制剂，以及利用它们生产药物制剂和相关方法治疗或抑制某些疾病或症状，包括疼痛。
• [EN] THIOPHENE -2- CARBOXYLIC ACID - (1H - BENZIMIDAZOL - 2 YL) - AMIDE DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE TEC KINASE ITK (INTERLEUKIN -2- INDUCIBLE T CELL KINASE) FOR THE TREATMENT OF INFLAMMATION, IMMUNOLOGICAL AND ALLERGIC DISORDERS<br/>[FR] DERIVES D'ACIDE THIOPHENE-2-CARBOXYLIQUE (1H-BENZIMIDAZOL-2 YL)-AMIDE ET COMPOSES ASSOCIES UTILISES COMME INHIBITEURS DE LA TEC KINASE ITK (KINASE DES LYMPHOCITES INDUCTIBLES PAR L'INTERLEUKINE -2) POUR TRAITER UNE INFLAMMATION ET DES TROUBLES IMMUNOLOGIQUES ET ALLERGIQUES
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2005079791A1

  公开（公告）日：2005-09-01

  Disclosed are compounds of formula (I): wherein Ar1, Ar2, R1, R2, R3, R4 and Xa are defined herein. The compounds of the invention inhibit Itk kinase and are therefore useful for treating diseases and pathological conditions involving inflammation, immunological disorders and allergic disorders. Also disclosed are processes for preparing these compounds and to pharmaceutical compositions comprising these compounds.

  揭示了式（I）的化合物：其中Ar1、Ar2、R1、R2、R3、R4和Xa在此定义。该发明的化合物抑制Itk激酶，因此对于治疗涉及炎症、免疫紊乱和过敏疾病的疾病和病理状况是有用的。还公开了制备这些化合物的方法以及包含这些化合物的药物组合物。