唑-5-羧酸 | 118994-90-4

• 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: 唑-5-羧酸
• 中文别名: 5-噁唑甲酸；恶唑-5-羧酸；5-恶唑甲酸；噁唑-5-甲酸；5-羧基唑；噁唑-5-羧酸
• 英文名称: 1,3-oxazole-5-carboxylic acid
• 英文别名: oxazole-5-carboxylic acid；5-Oxazolecarboxylic acid
• CAS: 118994-90-4
• 化学式: C₄H₃NO₃
• mdl: MFCD04114931
• 分子量: 113.073
• InChiKey: QCGMEWVZBGQOFN-UHFFFAOYSA-N

物化性质

• 熔点：
  195-197
• 沸点：
  289.3±13.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放于惰性气体中，避免与空气接触。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Oxazole-5-carboxylic acid
Product Name:
Synonyms: 5-Oxazolecarboxylic acid

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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.
Oxazole-5-carboxylic acid
Ingredient name:
CAS number: 118994-90-4

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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.
Store in closed vessels, under −20◦C.
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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C4H3NO3
Molecular weight: 113.1

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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.

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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

制备方法与用途

噁唑-5-羧酸是一种有机中间体，可通过氢氧化锂水解5-噁唑甲酸乙酯制得。文献报道该方法可用于制备GPR119激动剂。

其制备步骤如下：将49.44 kg 氢氧化锂一水合物溶解于319 kg水中，得到124.5 kg溶液（含398 mol），再将其加入到含有5-噁唑甲酸乙酯(54 kg, 382.7 mol)和54 kg水的溶液中，并保持反应温度低于25℃。搅拌6.5小时后，缓缓加入浓HCl水溶液（64.8 kg），并同样维持低温条件。然后将混合物冷却至5℃，保持1小时，使结晶析出。滤出产物，用88 kg冷水洗涤，再用异丙醇(171 kg)洗涤，并在50℃下真空干燥，最终得到标题化合物（产率87.5%，重37.88 kg）。

反应信息

• 作为反应物：
  描述：

  唑-5-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 oxazole-5-carbonyl chloride
  参考文献：
  名称：

  与莫匹罗星协同作用的新型金黄色葡萄球菌RnpA抑制剂

  摘要：

  我们最近发现RnpA是耐甲氧西林金黄色葡萄球菌（MRSA）的有希望的新药物发现靶标。RnpA是一种必需蛋白，被认为可以执行两个必需的细胞过程。作为RNA的一部分，Rnpa介导RNA降解。与rnpB结合可形成tRNA成熟所需的RNase P卤酶。高通量筛选确定RNPA2000是RnpA相关活性的抑制剂，对临床相关金黄色葡萄球菌具有抗菌活性。，包括MRSA。旨在提高效力并取代潜在的代谢毒性呋喃部分的结构活性研究导致鉴定出许多更有效的类似物。许多新的类似物具有明显的细胞毒性，因此不能用作抗生素，但包括衍生物5o在内的两种衍生物与莫匹罗星具有令人印象深刻的协同作用，后者是一种用于MSRA非定殖的抗生素，其有效性最近因细菌耐药性而受到损害。根据我们的研究结果，像5o这样的化合物可能最终可用于使对莫匹罗星耐药的细菌对莫匹罗星重新敏感。

  DOI：

  10.1016/j.bmcl.2018.01.022
• 作为产物：
  描述：

  噁唑-5-羧酸乙酯 在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 水 为溶剂， 反应 7.5h， 以87.4%的产率得到唑-5-羧酸
  参考文献：
  名称：

  C–H功能化在磷脂酰肌醇3-激酶Delta抑制剂Nemiralisib的聚合反应中的应用

  摘要：

  本文介绍了一种改进的可扩展方法，用于生产nemiralisib（一种磷脂酰肌醇-3-激酶δ抑制剂）。结合三个连续的催化反应，包括钯催化的C–H功能化和铱催化的硼化反应，显着简化并缩短了合成顺序。修订后的路线已在多千克规模的中试工厂中成功实施，以交付大于100千克的产品。

  DOI：

  10.1021/acs.oprd.0c00486

文献信息

• [EN] PYRIMIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS DE PYRIMIDINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：GENENTECH INC

  公开号：WO2010014939A1

  公开（公告）日：2010-02-04

  Disclosed are compounds of Formula I, including steroisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, that are useful in modulating PIKK related kinase signaling, e.g., mTOR, and for the treatment of diseases (e.g., cancer) that are mediated at least in part by the dysregulation of the PIKK signaling pathway (e.g., mTOR).

  揭示了公式I的化合物，包括立体异构体、几何异构体、互变异构体、溶剂合物、代谢物和其药学上可接受的盐，这些化合物在调节PIKK相关激酶信号传导方面很有用，例如mTOR，并用于治疗至少部分由PIKK信号传导途径失调引起的疾病（例如癌症）。
• [EN] COMPLEMENT MODULATORS AND RELATED METHODS<br/>[FR] MODULATEURS DU COMPLÉMENT ET PROCÉDÉS ASSOCIÉS
  申请人：RA PHARMACEUTICALS INC

  公开号：WO2020205501A1

  公开（公告）日：2020-10-08

  The present disclosure presents compounds and compositions that interact with complement components. Some compounds inhibit complement activity. Included are small molecule compounds and compositions that function as C5 inhibitor compounds. Methods for inhibiting complement activity and methods of treating complement-related indications with the C5 inhibitor compounds and compositions are provided.

  本公开涉及与补体成分相互作用的化合物和组合物。一些化合物抑制补体活性。包括作为C5抑制剂化合物的小分子化合物和组合物。提供了抑制补体活性的方法以及利用C5抑制剂化合物和组合物治疗与补体相关症状的方法。
• [EN] HETERO-1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONES<br/>[FR] HÉTÉRO-1,5,6,7-TÉTRAHYDRO-4H-INDOL-4-ONES
  申请人：BAYER PHARMA AG

  公开号：WO2017102649A1

  公开（公告）日：2017-06-22

  Compounds of formula (I) as described herein, processes for their production and their use as pharmaceuticals.

  本文件所述的式(I)化合物、其制备方法以及作为药物的用途。
• [EN] PYRROLIDINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF<br/>[FR] DÉRIVÉS DE PYRROLIDINE, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET UTILISATIONS ASSOCIÉES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014114578A1

  公开（公告）日：2014-07-31

  The invention relates to new pyrrolidine derivatives of the formula (I), to their use as medicaments, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  这项发明涉及公式（I）的新吡咯烷衍生物，其用作药物，用于其治疗用途的方法以及含有它们的药物组合物。
• Synthesis, microbiological evaluation and structure activity relationship analysis of linezolid analogues with different C5-acylamino substituents
  作者：Christos Matsingos、Taha Al-Adhami、Shirin Jamshidi、Charlotte Hind、Melanie Clifford、J. Mark Sutton、Khondaker Miraz Rahman

  DOI：10.1016/j.bmc.2021.116397

  日期：2021.11

  their efforts to develop new antibiotics by modifying existing antibiotic classes. We studied the SAR of the C5-acylaminomethyl moiety of the linezolid, an oxazolidinone antibiotic, by synthesizing 25 compounds containing various aromatic, heteroaromatic and aliphatic substitutions. Our findings suggest that this position is highly important for the function of this antibiotic class, since only smaller

  抗生素耐药性和缺乏新的抗生素来治疗耐多药 (MDR) 细菌是一个重大的公共卫生问题。存在一个发现空白，临床开发中的新型抗生素管道几乎是空的。因此，了解当前化学类别的结构活性关系 (SAR) 非常重要，因为这可以帮助药物发现社区通过修改现有抗生素类别来开发新抗生素。我们通过合成 25 种含有各种芳香族、杂芳香族和脂肪族取代的化合物，研究了利奈唑胺（一种恶唑烷酮类抗生素）的 C5-酰基氨基甲基部分的 SAR。我们的研究结果表明，这个位置对于这类抗生素的功能非常重要，因为与利奈唑胺相比，只有较小的非极性片段在该位置被耐受，而较大和极性的片段导致活性降低。我们的发现使我们围绕利奈唑胺的 C5-酰基氨基甲基部分构建了结构活性关系，这为恶唑烷酮类抗生素的功能提供了有价值的见解。