2-噻唑乙酸 | 188937-16-8

• 物质功能分类: 有机原料 - 杂环化合物
• 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-噻唑乙酸
• 中文别名: 2-(2-噻唑基)乙酸
• 英文名称: 2-(thiazol-2-yl)acetic acid
• 英文别名: 2-(1,3-thiazol-2-yl)acetic acid；2-thiazoleacetic acid
• CAS: 188937-16-8
• 化学式: C₅H₅NO₂S
• 分子量: 143.166
• InChiKey: YXTMFYBABGJSBY-UHFFFAOYSA-N

物化性质

• 沸点：
  296.0±23.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934100090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H319
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Thiazoleacetic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H319: Causes serious eye irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Thiazoleacetic acid
CAS number: 188937-16-8

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C5H5NO2S
Molecular weight: 143.2

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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, 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-噻唑乙酸 在 potassium acetate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 1,4-二氧六环 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.16h， 生成 6-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5H-thiazolo[3,2-c]pyrimidine-5,7(6H)-dione
  参考文献：
  名称：

  SUBSTITUTED TETRAHYDROCARBAZOLE AND CARBAZOLE CARBOXAMIDE COMPOUNDS

  摘要：

  公开的是Formula (I)的化合物，其中：两条虚线代表两个单键或两个双键；Q是：R1是F、Cl、—CN或—CH3；R2是Cl或—CH3；R3是—C(CH3)2OH或—CH2CH2OH；Ra是H或—CH3；每个Rb独立地是F、Cl、—CH3和/或—OCH3；n为零、1或2。还公开了将这些化合物用作Bruton酪氨酸激酶（Btk）抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓多种治疗领域的疾病或疾病的进展方面非常有用，如自身免疫疾病和血管疾病。

  公开号：

  US20140378475A1
• 作为产物：
  描述：

  ethyl 2-thiazolyl acetate 在 aqueous KOH 作用下， 生成 2-噻唑乙酸
  参考文献：
  名称：

  Inhibitors of protein isoprenyl transferases

  摘要：

  具有以下结构式或其药用可接受盐的化合物，其中R1为(a)氢，(b)较低烷基，(c)烯基，(d)烷氧基，(e)硫代烷氧基，(f)卤素，(g)卤代烷基，(h)芳基-L2—，和(i)杂环-L2—；R2选自(a) (b) —C(O)NH—CH(R14)—C(O)OR15，(d) —C(O)NH—CH(R14)—C(O)NHSO2R16，(e) —C(O)NH—CH(R14)-四唑基，(f) —C(O)NH-杂环，和(g) —C(O)NH—CH(R14)—C(O)NR17R18；R3为取代或未取代的杂环或芳基，取代或未取代的环烷基或环烯基，以及—P(W)RR3RR3′；R4为氢，较低烷基，卤代烷基，卤素，芳基，芳基烷基，杂环，或(杂环)烷基；L1为空缺或选自(a) —L4—N(R5)—L5—，(b) —L4—O—L5—，(c) —L4—S(O)n—L5—，(d) —L4—L6—C(W)—N(R5)—L5—，(e) —L4—L6—S(O)m—N(R5)—L5—，(f) —L4—N(R5)—C(W)—L7—L5—，(g) —L4—N(R5)—S(O)p—L7—L5—，(h)可选择取代的烷基，(i)可选择取代的烯基，(j)可选择取代的炔基，(k)共价键，(l)和(m)是蛋白异戊二烯基转移酶的抑制剂。还公开了蛋白异戊二烯基转移酶抑制剂组合物和抑制蛋白异戊二烯基转移酶的方法。

  公开号：

  US06310095B1

文献信息

• Zur Kenntnis der Thiazol-essigsäuren
  作者：R. Mory、H. Schenkel

  DOI：10.1002/hlca.19500330225

  日期：——

  Es wird die Synthese der Thiazol-2-essigsäure und der Thiazol-5-essigsäure sowie einiger Derivate dieser Verbindungen beschrieben.

  描述了噻唑-2-乙酸和噻唑-5-乙酸以及这些化合物的一些衍生物的合成。
• SAR evolution towards potent C-terminal carboxamide peptide inhibitors of Zika virus NS2B-NS3 protease
  作者：Stefania Colarusso、Federica Ferrigno、Simona Ponzi、Francesca Pavone、Immacolata Conte、Luigi Abate、Elisa Beghetto、Antonino Missineo、Jerome Amaudrut、Alberto Bresciani、Giacomo Paonessa、Licia Tomei、Christian Montalbetti、Elisabetta Bianchi、Carlo Toniatti、Jesus M. Ontoria

  DOI：10.1016/j.bmc.2022.116631

  日期：2022.3

  Zika virus (ZIKV) is a member of the Flaviviridae family that can cause neurological disorders and congenital malformations. The NS2B-NS3 viral serine protease is an attractive target for the development of new antiviral agents against ZIKV. We report here a SAR study on a series of substrate-like linear tripeptides that inhibit in a non-covalent manner the NS2B-NS3 protease. Optimization of the residues

  寨卡病毒 (ZIKV) 是黄病毒科的成员，可导致神经系统疾病和先天性畸形。NS2B-NS3 病毒丝氨酸蛋白酶是开发针对 ZIKV 的新抗病毒药物的有吸引力的目标。我们在此报告了对以非共价方式抑制 NS2B- 蛋白酶的一系列底物样线性三肽的 SAR 研究。优化位置P 1、P 2、P 3 和N的残基三肽的-末端和C-末端部分允许鉴定具有亚微摩尔效力的抑制剂，其中苯基甘氨酸作为精氨酸模拟基团和苯甲酰胺作为C-末端片段。进一步的 SAR 探索和将这些结构变化应用于在P 1 位具有 4 个取代的苯基甘氨酸残基的一系列肽，导致有效的化合物显示出对寨卡蛋白酶 (IC 50  = 30 nM) 具有高选择性的两位数纳摩尔抑制作用胰蛋白酶样蛋白酶和其他黄病毒的蛋白酶，例如登革热 2 病毒 (DEN2V) 和西尼罗河病毒 (WNV)。
• [EN] CARBAZOLE CARBOXAMIDE COMPOUNDS USEFUL AS KINASE INHIBITORS<br/>[FR] COMPOSÉS DE CARBAZOLE-CARBOXAMIDE UTILES COMME INHIBITEURS DE KINASES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2014210087A1

  公开（公告）日：2014-12-31

  Disclosed are compounds of Formula (I); and salts thereof, wherein:Formula (II); Q is: R1 is -C(CH3)2OH, -NHC(=0)C(CH3)3, -N(CH3)2, or -CH2Rd; R2 is CI or -CH3; R3 is H, F, or -CH3; Ra is H or -CH3; Rb is H, F, CI, or -OCH3 Rc is H or F; and Rd is -OH, -OCH3, -NHC(=0)CH3, or fORMULA (III), Also disclosed are methods of using such compounds as inhibitors of Bruton's tyrosine kinase (Btk), and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  公开了Formula (I)的化合物及其盐，其中：Formula (II)；Q是：R1为-C(CH3)2OH，-NHC(=0)C( )3，-N( )2，或-CH2Rd；R2为CI或- ；R3为H，F或- ；Ra为H或- ；Rb为H，F，CI或-O ；Rc为H或F；Rd为-OH，-O ，-NHC(=0) ，或Formula (III)。还公开了使用这些化合物作为Bruton酪氨酸激酶（Btk）抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓各种治疗领域的疾病或障碍方面具有用途，如自身免疫疾病和血管疾病。
• Synthesis of Fused Imidazole-Containing Ring Systems via Dual Oxidative Amination of C(sp³)–H Bonds
  作者：Georgette Castanedo、Yanzhou Liu、James J. Crawford、Marie-Gabrielle Braun

  DOI：10.1021/acs.joc.6b01517

  日期：2016.9.16

  A general and efficient method for a metal-free one-pot synthesis of highly substituted fused imidazole-containing 5,5- and 5,6-fused bicyclic heterocycles is described. Starting from commercially available substrates and reagents, the reaction proceeds through two C–N bond formations and an oxidative dehydrogenation to form highly substituted products in good to excellent yield.

  描述了一种通用且有效的方法，用于无金属一锅合成高度取代的稠合的含咪唑的5,5-和5,6-稠合的双环杂环。从可商购的底物和试剂开始，该反应通过两个C–N键的形成和氧化脱氢进行，以形成高取代率的产品，收率好至极好。
• AZD0284, a Potent, Selective, and Orally Bioavailable Inverse Agonist of Retinoic Acid Receptor-Related Orphan Receptor C2
  作者：Frank Narjes、Antonio Llinas、Stefan von Berg、Johan Jirholt、Sarah Lever、Rikard Pehrson、Mia Collins、Anna Malmberg、Petter Svanberg、Yafeng Xue、Roine I. Olsson、Jesper Malmberg、Glyn Hughes、Nafizal Hossain、Hanna Grindebacke、Agnes Leffler、Nina Krutrök、Elisabeth Bäck、Marie Ramnegård、Matti Lepistö、Linda Thunberg、Anna Aagaard、Jane McPheat、Eva L. Hansson、Rongfeng Chen、Yao Xiong、Thomas G. Hansson

  DOI：10.1021/acs.jmedchem.1c01197

  日期：2021.9.23

  Inverse agonists of the nuclear receptor RORC2 have been widely pursued as a potential treatment for a variety of autoimmune diseases. We have discovered a novel series of isoindoline-based inverse agonists of the nuclear receptor RORC2, derived from our recently disclosed RORC2 inverse agonist 2. Extensive structure–activity relationship (SAR) studies resulted in AZD0284 (20), which combined potent

  核受体 RORC2 的反向激动剂已被广泛视为多种自身免疫性疾病的潜在治疗方法。我们发现了一系列新型的基于异吲哚啉的核受体 RORC2 反向激动剂，源自我们最近公开的 RORC2 反向激动剂2 。广泛的构效关系 (SAR) 研究产生了 AZD0284 ( 20 )，它结合了对原代人 T H 17 细胞 IL-17A 分泌的有效抑制，在临床前物种中具有出色的代谢稳定性和良好的 PK。在两项临床前体内研究中，化合物20减少了小鼠胸腺细胞数量，并在咪喹莫特诱导的炎症模型中显示出含有 IL-17A 的 γδ-T 细胞以及 IL-17A 和 IL-22 RNA 的剂量依赖性减少。基于这些数据和良好的安全性， 20 项研究已进入 1 期临床研究。