4-氨基-6-吗啉并嘧啶 | 96225-80-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-氨基-6-吗啉并嘧啶
• 中文别名: 4-氨基-6-吗啉基嘧啶
• 英文名称: 6-(morpholin-4-yl)pyrimidin-4-amine
• 英文别名: 6-morpholinopyrimidin-4-amine；6-morpholino-pyrimidin-4-ylamine；6-Morpholino-pyrimidin-4-ylamin；6-Morpholin-4-yl-pyrimidin-4-ylamine；4-amino-6-(4-morpholino)pyrimidine；4-Amino-6-morpholinopyrimidine；6-morpholin-4-ylpyrimidin-4-amine
• CAS: 96225-80-8
• 化学式: C₈H₁₂N₄O
• 分子量: 180.209
• InChiKey: XQOJWZMBGGYWCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  2-8℃，避光保存，放置于干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Amino-6-morpholinopyrimidine
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: 4-Amino-6-morpholinopyrimidine
CAS number: 96225-80-8

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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.
Store in closed vessels, refrigerated.
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: C8H12N4O
Molecular weight: 180.2

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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.

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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：

  异硫氰酸乙酯 、 4-氨基-6-吗啉并嘧啶 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以54%的产率得到1-ethyl-3-(6-morpholine pyrimidin-4-yl)thiourea
  参考文献：
  名称：

  Development of Multifunctional Pyrimidinylthiourea Derivatives as Potential Anti-Alzheimer Agents

  摘要：

  Starting from a screening-hit compound, via structure modifications and optimizations, a series of nonfused and nonassembly pyrimidinylthiourea derivatives (2-5) was designed, synthesized, and evaluated as novel multifunctional agents against Alzheimer's disease. Biological activity results demonstrated that compounds 5r and 5t exhibited potent inhibition and excellent selectivity toward acetylcholinesterase (AChE, Sr, IC50 = 0.204 mu M, SI > 196; St, IC50 = 0.067 mu M, SI > 597), specific metal-chelating ability, significant antioxidant effects, modulation of metal-induced A beta aggregation, inhibition of ROS production by copper redox cycle, low cytotoxicity, and moderate neuroprotection to human neuroblastoma SH-SY5Y cells. Moreover, compound Sr displayed appropriate blood brain barrier (BBB) permeability both in vitro and in vivo and could improve memory and cognitive function of, scopolamine-induced amnesia mice. The multifunctional profiles of Sr and its effectivity in AD mice highlight these structurally distinct pyrimidinylthiourea derivatives as prospective prototypes in the research of innovative multifunctional drugs for Alzheimer's disease.

  DOI：

  10.1021/acs.jmedchem.6b00636
• 作为产物：
  描述：

  吗啉 、 4-氨基-6-氯嘧啶 以 甲苯 为溶剂， 反应 24.0h， 以89%的产率得到4-氨基-6-吗啉并嘧啶
  参考文献：
  名称：

  吡啶酮-氨基衍生物作为MNK1 / 2抑制剂的设计，合成和生物学评估。

  摘要：

  真核翻译起始因子4E（eIF4E）的过度磷酸化在mRNA翻译失调和肿瘤细胞信号激活中起主要作用。eIF4E仅被Ser209上的促分裂原活化蛋白激酶相互作用的激酶1和2（MNK1 / 2）磷酸化。因此，MNK1 / 2抑制剂可以降低p-eIF4E的水平并调节肿瘤相关的信号通路。合成了一系列吡啶酮-氨基衍生物，并作为MNK1 / 2抑制剂进行了评估。几种化合物对MNK1 / 2表现出极大的抑制活性，某些化合物对血液癌细胞系表现出中度至优异的抗增殖能力。特别地，化合物42i（MNK1 IC50 = 7.0 nM； MNK2 IC50 = 6.1 nM）被证明是针对TMD-8细胞系最有效的化合物，IC50值为0.91μM。此外，42i可以阻断CT-26细胞系中eIF4E的磷酸化水平，42i可以显着抑制CT-26同种异体移植模型的肿瘤生长。这些结果表明，化合物42i是有效治疗结肠癌的有希望的MNK1

  DOI：

  10.1016/j.bmc.2019.02.007

文献信息

• COMPOUNDS AND METHODS FOR TREATING CANCER
  申请人：ANTIDOTE IP HOLDINGS, LLC

  公开号：US20200299282A1

  公开（公告）日：2020-09-24

  Substituted cinnamamide compounds and analogs, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or ameliorate cancer are provided.

  提供了替代肉桂酰胺化合物和类似物、制备这类化合物的方法、包含这类化合物的药物组合物和药物、以及使用这类化合物治疗、预防或改善癌症的方法。
• 取代嘧啶脲类化合物及其用途
  申请人：华东理工大学

  公开号：CN105418592B

  公开（公告）日：2018-02-16

  本发明涉及一种取代嘧啶脲类化合物及其用途。所述取代嘧啶脲类化合物为式I所示化合物(具体结构请见说明书或权利要求书)、或其立体异构体或药学上可接受的盐。体外活性测试表明：本发明公开的取代嘧啶脲类化合物具有胆碱酯酶抑制活性、螯合金属离子、抑制金属离子诱导的自由基产生和抑制金属离子诱导的Aβ聚集等性能。因此，本发明提供的取代嘧啶脲类化合物有望被用于制备治疗和/或预防阿尔茨海默病药物。
• [EN] AZABENZOTHIAZOLE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS D'AZABENZOTHIAZOLE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012035039A1

  公开（公告）日：2012-03-22

  Provided are compounds of Formula I, stereoisomers, tautomers, solvates, prodrugs and pharmaceutically acceptable salts thereof, wherein A, X, R1, R2, R4 and R5 are defined herein, a pharmaceutical composition that includes a compound of Formula I and a pharmaceutically acceptable carrier, adjuvant or vehicle, methods of using the compound or composition in therapy, and methods of 5 manufacturing a compound of Formula I.

  提供的是公式I的化合物，立体异构体，互变异构体，溶剂合物，前药和其药学上可接受的盐，其中A、X、R1、R2、R4和R5在此处被定义，包括公式I的化合物和药学上可接受的载体、辅料或载体的药物组合物，使用该化合物或组合物进行治疗的方法，以及制造公式I的化合物的方法。
• Tyrosine kinase inhibitors
  申请人：——

  公开号：US20020137755A1

  公开（公告）日：2002-09-26

  The present invention relates to compounds which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angiogenesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, inflammatory diseases, and the like in mammals.

  本发明涉及抑制、调节和/或调控酪氨酸激酶信号传导的化合物，含有这些化合物的组合物，以及使用它们治疗依赖于酪氨酸激酶的疾病和病况的方法，如在哺乳动物中的血管生成、癌症、肿瘤生长、动脉粥样硬化、老年性黄斑变性、糖尿病视网膜病变、炎症性疾病等。
• 2-Aminothiazole as a Novel Kinase Inhibitor Template. Structure−Activity Relationship Studies toward the Discovery of <i>N</i>-(2-Chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1- piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (Dasatinib, BMS-354825) as a Potent <i>pan</i>-Src Kinase Inhibitor
  作者：Jagabandhu Das、Ping Chen、Derek Norris、Ramesh Padmanabha、James Lin、Robert V. Moquin、Zhongqi Shen、Lynda S. Cook、Arthur M. Doweyko、Sidney Pitt、Suhong Pang、Ding Ren Shen、Qiong Fang、Henry F. de Fex、Kim W. McIntyre、David J. Shuster、Kathleen M. Gillooly、Kamelia Behnia、Gary L. Schieven、John Wityak、Joel C. Barrish

  DOI：10.1021/jm060727j

  日期：2006.11.1

  2-aminothiazole (1) was discovered as a novel Src family kinase inhibitor template through screening of our internal compound collection. Optimization through successive structure-activity relationship iterations identified analogs 2 (Dasatinib, BMS-354825) and 12m as pan-Src inhibitors with nanomolar to subnanomolar potencies in biochemical and cellular assays. Molecular modeling was used to construct

  通过筛选我们的内部化合物集合，发现了2-氨基噻唑（1）作为一种新型Src家族激酶抑制剂模板。通过连续的结构-活性关系迭代进行的优化确定了类似物2（Dasatinib，BMS-354825）和12m是在生化和细胞分析中具有纳摩尔至亚纳摩尔浓度的pan-Src抑制剂。分子模型被用来构建推定的结合模型，以抑制这类化合物对Lck的抑制作用。该模型提出的关键氢键相互作用的框架与随后公布的与结构相似的Abl激酶结合的2的晶体结构一致。此类抑制剂的口服药效为12m，可在小鼠体内体外抑制促炎细胞因子IL-2（ED50约为5 mg / kg），并在急性小鼠炎症模型中降低TNF水平（LPS抑制90％） LPS给药前2小时以60 mg / kg口服给药时，TNF-α诱导的TNFα产生）。当每天两次以0.3和3 mg / kg口服给药时，在已确诊疾病的大鼠的慢性佐剂性关节炎模型中进一步证明了12m的口服功效。达沙