2-氨基-4-环丙基噻唑-5-羧酸甲酯 | 1065074-61-4

• 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-氨基-4-环丙基噻唑-5-羧酸甲酯
• 英文名称: methyl 2-amino-4-cyclopropylthiazole-5-carboxylate
• 英文别名: methyl 2-amino-4-cyclopropyl-1,3-thiazole-5-carboxylate
• CAS: 1065074-61-4
• 化学式: C₈H₁₀N₂O₂S
• mdl: MFCD11053814
• 分子量: 198.246
• InChiKey: QRLSMSRWINQRJB-UHFFFAOYSA-N

物化性质

• 沸点：
  354.2±30.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934100090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 2-amino-4-cyclopropylthiazole-5-carboxylate
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: Methyl 2-amino-4-cyclopropylthiazole-5-carboxylate
CAS number: 1065074-61-4

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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: C8H10N2O2S
Molecular weight: 198.2

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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-氨基-4-环丙基噻唑-5-羧酸甲酯 在 盐酸 、 potassium trimethylsilonate 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 77.0h， 生成 4-cyclopropyl-2-methoxythiazole-5-carboxylic acid
  参考文献：
  名称：

  Optimization of Brain Penetrant 11β-Hydroxysteroid Dehydrogenase Type I Inhibitors and in Vivo Testing in Diet-Induced Obese Mice

  摘要：

  11 beta-Hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) has been widely considered by the pharmaceutical industry as a target to treat metabolic syndrome in type II diabetics. We hypothesized that central nervous system (CNS) penetration might be required to see efficacy. Starting from a previously reported pyrimidine compound, we removed hydrogen-bond donors to yield 3, which had modest CNS penetration. More significant progress was achieved by changing the core to give 40, which combines good potency and CNS penetration. Compound 40 was dosed to diet-induced obese (DIO) mice and gave excellent target engagement in the liver and high free exposures of drug, both peripherally and in the CNS. However, no body weight reduction or effects on glucose or insulin were observed in this model. Similar data were obtained with a structurally diverse thiazole compound 51. This work casts doubt on the hypothesis that localized tissue modulation of 11 beta-HSD1 activity alleviates metabolic syndrome.

  DOI：

  10.1021/jm4016729
• 作为产物：
  描述：

  3-环丙基-3-氧代丙酸甲酯 在 magnesium perchlorate 、 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 14.6h， 生成 2-氨基-4-环丙基噻唑-5-羧酸甲酯
  参考文献：
  名称：

  磺酰胺类衍生物及其制备方法和用途

  摘要：

  本发明涉及一类磺胺类衍生物，以及包含该类化合物的药物组合物。所述化合物或药物组合物可用于抑制尿酸盐阴离子转运体。本发明还涉及制备这类化合物和药物组合物的方法，以及它们在治疗或预防哺乳动物，特别是人类，与血中尿酸值偏高有关的疾病的用途。

  公开号：

  CN107089955B

文献信息

• 磺酰胺类衍生物及其制备方法和用途
  申请人：广东东阳光药业有限公司

  公开号：CN107089955B

  公开（公告）日：2020-10-23

  本发明涉及一类磺胺类衍生物，以及包含该类化合物的药物组合物。所述化合物或药物组合物可用于抑制尿酸盐阴离子转运体。本发明还涉及制备这类化合物和药物组合物的方法，以及它们在治疗或预防哺乳动物，特别是人类，与血中尿酸值偏高有关的疾病的用途。
• Synthesis and antimicrobial evaluation of novel ethyl 2-(2-(4-substituted)acetamido)-4-subtituted-thiazole-5-carboxylate derivatives
  作者：Chandrakant D. Pawar、Aniket P. Sarkate、Kshipra S. Karnik、Sushilkumar S. Bahekar、Dattatraya N. Pansare、Rohini N. Shelke、Chetan S. Jawale、Devanand B. Shinde

  DOI：10.1016/j.bmcl.2016.06.030

  日期：2016.8

  A series of novel molecules containing thiazole ring structure were designed and synthesized. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, 13C NMR, Mass spectrum and the purity was checked through HPLC analysis. Among these synthesized compounds, 3a–3i and 6a–6c were tested for their antimicrobial activity (minimum inhibitory concentration) against a series of

  设计并合成了一系列含有噻唑环结构的新型分子。阐明合成的化合物的结构，并通过1 H NMR，13 C NMR，质谱确认，并通过HPLC分析检查纯度。在这些合成的化合物中，测试了3a - 3i和6a - 6c对一系列枯草芽孢杆菌，金黄色葡萄球菌和大肠杆菌菌株的抗菌活性（最低抑菌浓度）以及对白色念珠菌，黄曲霉菌株的抗菌活性。和黑曲霉分别具有抗真菌活性。抗菌筛选数据的结果表明，大多数受试化合物均显示出中度至良好的微生物抑制作用。
• TRIAZOLE DERIVATIVE OR SALT THEREOF
  申请人：Yoshimura Seiji

  公开号：US20110105460A1

  公开（公告）日：2011-05-05

  [Problem] A compound, which can be used for preventing or treating diseases, in which 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) is concerned, in particular, diabetes, insulin resistance, dementia, schizophrenia and depression, is provided. [Means for Solution] It was found that a triazole derivative, in which one of the 3- and 5-positions of the triazole ring has (di)alkylmethyl or cycloalkyl, each of which is substituted with —O— (aryl or a heterocyclic group, each of which may be substituted, or lower alkylene-cycloalkyl), and the other thereof has aryl, a heterocyclic group or cycloalkyl, each of which may be substituted, or a pharmaceutically acceptable salt thereof exhibits potent 11β-HSD1 inhibitory action. From the above, the triazole derivative of the present invention can be used for preventing or treating diabetes, insulin resistance, dementia, schizophrenia and depression.

  [问题] 提供一种可用于预防或治疗疾病的化合物，其中涉及11β-羟基类固醇脱氢酶1型（11β-HSD1），特别是糖尿病、胰岛素抵抗、痴呆症、精神分裂症和抑郁症。 [解决方案] 发现一种三唑衍生物，其中三唑环的3-和5-位置之一具有（二）烷基甲基或环烷基，每个基团都被取代为-O-（苯基或杂环基，每个基团都可以被取代，或较低的烷基-环烷基），另一个位置具有苯基、杂环基或环烷基，每个基团都可以被取代，或其药学上可接受的盐，表现出强效的11β-HSD1抑制作用。因此，本发明的三唑衍生物可用于预防或治疗糖尿病、胰岛素抵抗、痴呆症、精神分裂症和抑郁症。
• US8377923B2
  申请人：——

  公开号：US8377923B2

  公开（公告）日：2013-02-19
• [EN] TRIAZOLE DERIVATIVE OR SALT THEREOF<br/>[FR] DÉRIVÉ DE TRIAZOLE OU SEL DE CELUI-CI
  申请人：ASTELLAS PHARMA INC

  公开号：WO2010001946A1

  公开（公告）日：2010-01-07

  【課題】11β-ヒドロキシステロイド デヒドロゲナーゼ タイプ１（１１β－ＨＳＤ１）が関与する疾患、特に糖尿病、インスリン抵抗性、認知症、統合失調症、うつの予防又は治療に用いることができる化合物の提供。 【解決手段】トリアゾール環の３位及び5位の、一方に-O-（それぞれ置換されていてもよいアリール若しくはヘテロ環基、又は、低級アルキレン-シクロアルキル）でそれぞれ置換された（ジ）アルキルメチル又はシクロアルキル、他方にそれぞれ置換されていてもよいアリール、ヘテロ環基又はシクロアルキルを有することを特徴とするトリアゾール誘導体またはその製薬学的に許容される塩が強力な１１β－ＨＳＤ１阻害活性を有することを見出した。このことから、本発明のトリアゾール誘導体は糖尿病、インスリン抵抗性、認知症、統合失調症、うつの予防又は治療に用いることができる。