5-氨基-3-甲基-异噻唑-4-羧酸 | 22131-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-3-甲基-异噻唑-4-羧酸
• 中文别名: 5-氨基-3-甲基异噻唑-4-羧酸
• 英文名称: 5-amino-3-methyl-1,2-thiazole-4-carboxylic acid
• 英文别名: 3-methyl-5-aminoisothiazole-4-carboxylic acid；5-amino-3-methyl-4-isothiazolecarboxylic acid；5-amino-3-methyl-isothiazole-4-carboxylic acid；3-Methyl-4-carboxy-5-amino-isothiazol；5-Amino-3-methylisothiazole-4-carboxylic acid
• CAS: 22131-51-7
• 化学式: C₅H₆N₂O₂S
• mdl: MFCD06376749
• 分子量: 158.181
• InChiKey: AQBUEVXOULPURO-UHFFFAOYSA-N

物化性质

• 沸点：
  220.2±40.0 °C(Predicted)
• 密度：
  1.532±0.06 g/cm3(Predicted)
• 溶解度：
  >23.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Amino-3-methylisothiazole-4-carboxylic acid
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: 5-Amino-3-methylisothiazole-4-carboxylic acid
CAS number: 22131-51-7

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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: C5H6N2O2S
Molecular weight: 158.2

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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：

  5-氨基-3-甲基-异噻唑-4-羧酸 在 吡啶 、 氯甲酸乙酯 作用下， 以 吡啶 、 二氯甲烷 、 丙酮 为溶剂， 反应 30.0h， 生成 5-(4-Chloro-benzoylamino)-3-methyl-isothiazole-4-carboxylic acid phenylamide
  参考文献：
  名称：

  新异噻唑衍生物：合成、反应性、理化性质和药理活性

  摘要：

  介绍了5-(4-氯苯甲酰基)氨基-3-甲基-4-异噻唑甲酸5的酰胺和酯衍生物10-20系列的合成和生物学研究。因为5-苯甲酰氨基-3-甲基-4-异噻唑甲酸2的酰胺系列已被广泛研究，并且从该系列中得诺替韦（vratizolin）4 [1, 2]成为抗病毒药物。此处讨论将异噻唑环 5 位的 N-苯甲酰基交换为 N-（4-氯苯甲酰基）基团对 5-苯甲酰氨基-3-甲基-4-异噻唑甲酸 2 衍生物药理活性的影响。讨论了5-(4-氯苯甲酰基)氨基-3-甲基-4-异噻唑甲酸5系列衍生物羧基结构修饰对其生物活性的影响。一些测试的 5-（4-氯苯甲酰基）氨基-3-甲基-4-异噻唑羧酰胺在角叉菜胶引起的水肿和气囊炎症试验中显示出显着的抗炎活性。描述了6-(4-氯苯基)-3-甲基异噻唑并[5,4-d]-4H-1,3-恶嗪-4-one 6的理化性质。还介绍了其在异噻唑衍生物合成中的用途及其反应性。

  DOI：

  10.1002/ardp.200500040
• 作为产物：
  描述：

  5-氨基-3-甲基异噻唑-4-羧酸乙酯 在 sodium hydroxide 作用下， 生成 5-氨基-3-甲基-异噻唑-4-羧酸
  参考文献：
  名称：

  Goerdeler,J.; Horn,H., Chemische Berichte, 1963, vol. 96, p. 1551 - 1560

  摘要：

  DOI：
• 作为试剂：
  描述：

  5-氨基-3-甲基-异噻唑-4-羧酸 、 氯化亚砜 、 6-(2,4-Difluorophenoxy)pyridin-3-amine 、 三乙胺 、 在 5-氨基-3-甲基-异噻唑-4-羧酸 、 acid chloride 、 甲苯 、 四氢呋喃 、 crude material 、 ethyl acetate n-hexane 作用下， 反应 7.75h， 以to yield 170 mg (16% yield of theory) of the title compound的产率得到5-Amino-N-[6-(2,4-difluorophenoxyl)pyridin-3-yl]-3-methyl-1,2-thiazole-4-carboxamide
  参考文献：
  名称：

  AMINO-SUBSTITUTED ISOTHIAZOLES

  摘要：

  本发明涉及通式（I）的异噻唑类化合物，其抑制有丝分裂检查点：其中A，R1和R2如权利要求书所定义的那样，以及制备该化合物的方法，用于制备该化合物的中间体化合物，包括该化合物的药物组合物和组合物，以及使用该化合物制造用于治疗或预防疾病的药物组合物，特别是肿瘤，作为唯一的制剂或与其他活性成分联合使用。

  公开号：

  US20150368260A1

文献信息

• [EN] AMINO-SUBSTITUTED ISOTHIAZOLES<br/>[FR] ISOTHIAZOLES AMINO-SUBSTITUÉS
  申请人：BAYER PHARMA AG

  公开号：WO2014118186A1

  公开（公告）日：2014-08-07

  The present invention relates to isothiazoles of general formula (I) which inhibit the mitotic checkpoint : in which A, R1 and R2 are as defined in the claims, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neoplasms, as a sole agent or in combination with other active ingredients.

  本发明涉及通式（I）的异噻唑类化合物，其抑制有丝分裂检查点：其中A、R1和R2如权利要求中所定义，以及制备所述化合物的方法，用于制备所述化合物的有用中间体化合物，包含所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是肿瘤，作为唯一药剂或与其他活性成分组合使用。
• Synthesis and experimental versus theoretical research on spectroscopic and electronic properties of 3-methyl-4-nitroisothiazole
  作者：Andrzej Regiec、Piotr Wojciechowski

  DOI：10.1016/j.molstruc.2019.06.028

  日期：2019.11

  UV-Vis spectra analysis reveals a nature of valence electron excitation and electron transition of 3-methyl-4-nitroisothiazole. Besides, unambiguous assignment of NMR signal shifts of carbon atoms of isothiazole ring of 3-methyl-4-nitroisothiazole, 5-amino-3-methylisothiazole and intermediate and side products of synthesis was conducted thanks to full detailed analysis of 1H, 13C NMR spectra and their

  摘要 提出并描述了合成有价值的 5-氨基-3-甲基异噻唑和 3-甲基-4-硝基异噻唑的替代方法。似乎新的、未描述的 3,3'-二甲基-4,4'-二硝基-5,5'-双异噻唑在合成过程中作为副产物产生。3-甲基-4-硝基异噻唑的实验和计算光谱和电子性质已被广泛研究和讨论。完整的振动分配是基于势能分布 PED 进行的。给出了完全非谐波红外和拉曼光谱，计算出基带、泛音和组合带的非谐波强度。由非谐波近似预测的振动谱与实验数据非常吻合。使用自然键轨道 (NBO 6.0) 分析估计了由超共轭相互作用产生的 3-甲基-4-硝基异噻唑分子的稳定性。结合前沿分子轨道和经典分子轨道的NBO分析用于预测3-甲基-4-硝基异噻唑分子最可能接受和脱离单电子的位点。测量的 3-甲基-4-硝基异噻唑的还原电位和计算的电子亲和性表明，该化合物在与 1-甲基-3-硝基吡唑相似的水平下易于还原，并且这种敏感性远高于各自的 1-甲基-4-硝基吡唑。UV-Vis
• New Amides of 5-Acylamino-3-Methyl-4-Isothiazolecarboxylic Acid and their Immunotropic Activity
  作者：Urszula Lipnicka、Andrzej Regiec、Emil Sułkowski、Michał Zimecki

  DOI：10.1002/ardp.200400903

  日期：2005.7

  Several new amides 4 of 5‐substituted 3‐methyl‐4‐isothiazolecarboxylic acid were obtained. These compounds have acetylamino or benzoylamino groups in position 5 of the isothiazole ring. In position 4, the carboxylic group was transformed in the amides using amino‐acid esters. Activities of the obtained derivatives were checked in the humoral immune response and delayed type hypersensitivity reaction

  得到了几种新的5-取代3-甲基-4-异噻唑甲酸酰胺4。这些化合物在异噻唑环的 5 位具有乙酰氨基或苯甲酰氨基。在第 4 位，羧基使用氨基酸酯转化为酰胺。在体液免疫反应和体内绵羊红细胞（SRBCs）的迟发型超敏反应中检查了所得衍生物的活性。
• Burak; Machon, Pharmazie, 1992, vol. 47, # 7, p. 492 - 495
  作者：Burak、Machon

  DOI：——

  日期：——
• Rajappa,S. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1976, vol. 14, p. 391 - 393
  作者：Rajappa,S. et al.

  DOI：——

  日期：——