2-氨基嘧啶-5-羧酸 | 3167-50-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-氨基嘧啶-5-羧酸
• 中文别名: 2-氨基嘧啶-5-甲酸
• 英文名称: 2-aminopyrimidine-5-carboxylic acid
• 英文别名: 2-Amino-5-pyrimidincarbonsaeure
• CAS: 3167-50-8
• 化学式: C₅H₅N₃O₂
• 分子量: 139.114
• InChiKey: CBRLWSXYXSFYSP-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  474.6±37.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25,S36/37
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Aminopyrimidine-5-carboxylic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
Wear protective gloves/protective clothing/eye protection/face protection
P280:

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Aminopyrimidine-5-carboxylic acid
CAS number: 3167-50-8

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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, refrigerated.

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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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C5H5N3O2
Molecular weight: 139.1

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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

反应信息

• 作为反应物：
  描述：

  2-氨基嘧啶-5-羧酸 反应 3.0h， 以74%的产率得到1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)-
  参考文献：
  名称：

  Schenone, Pietro; Sansebastiano, Laura; Mosti, Luisa, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 295 - 305

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯嘧啶-5-羧酸乙酯 在 氨 作用下， 生成 2-氨基嘧啶-5-羧酸
  参考文献：
  名称：

  Synthesis of Derivatives of Pyrimidine-5-carboxylic Acid¹

  摘要：

  DOI：

  10.1021/ja01256a016
• 作为试剂：
  描述：

  7-Methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine 、 2-氨基嘧啶-5-羧酸 在 2-氨基嘧啶-5-羧酸 作用下， 以11的产率得到2-amino-N-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyrimidine-5-carboxamide;dihydrochloride
  参考文献：
  名称：

  WO2008070150A1

  摘要：

  公开号：

文献信息

• Discovery and SAR of Novel 2,3-Dihydroimidazo[1,2-<i>c</i>]quinazoline PI3K Inhibitors: Identification of Copanlisib (BAY 80-6946)
  作者：William J. Scott、Martin F. Hentemann、R. Bruce Rowley、Cathy O. Bull、Susan Jenkins、Ann M. Bullion、Jeffrey Johnson、Anikó Redman、Arthur H. Robbins、William Esler、R. Paul Fracasso、Timothy Garrison、Mark Hamilton、Martin Michels、Jill E. Wood、Dean P. Wilkie、Hong Xiao、Joan Levy、Enrico Stasik、Ningshu Liu、Martina Schaefer、Michael Brands、Julien Lefranc

  DOI：10.1002/cmdc.201600148

  日期：2016.7.19

  cancers. As such, the development of PI3K inhibitors from novel compound classes should lead to differential pharmacological and pharmacokinetic profiles and allow exploration in various indications, combinations, and dosing regimens. A screening effort aimed at the identification of PI3Kγ inhibitors for the treatment of inflammatory diseases led to the discovery of the novel 2,3‐dihydroimidazo[1,2‐c]quinazoline

  磷酸肌醇3激酶（PI3K）途径在许多疾病状态中都被异常激活，包括肿瘤细胞，无论是通过生长因子受体酪氨酸激酶还是通过关键途径成分的基因突变和扩增。多种PI3K亚型在癌症中起着不同的作用。因此，从新型化合物类别开发PI3K抑制剂应导致不同的药理和药代动力学特征，并允许探索各种适应症，组合和给药方案。旨在鉴定用于治疗炎性疾病的PI3Kγ抑制剂的筛选工作导致发现了新型2,3-二氢咪唑[1,2- c喹唑啉类的PI3K抑制剂。随后针对癌症治疗的前导优化程序着重于抑制PI3Kα和PI3Kβ。在此，描述了此类的初始结构-活性关系发现以及优化方法，该方法导致将copanlisib（BAY 80-6946）鉴定为治疗实体瘤和血液肿瘤的临床候选药物。
• Discovery and evaluation of novel FAAH inhibitors in neuropathic pain model
  作者：Debnath Bhuniya、Rajendra K. Kharul、Atul Hajare、Nadim Shaikh、Sandeep Bhosale、Sandip Balwe、Fouzia Begum、Siddhartha De、Sonalee Athavankar、Dhananjay Joshi、Vamsi Madgula、Kaushal Joshi、Amol A. Raje、Ashwinkumar V. Meru、Amol Magdum、Kasim A. Mookhtiar、Rashmi Barbhaiya

  DOI：10.1016/j.bmcl.2018.11.048

  日期：2019.1

  marking irreversible inhibitor of fatty acid amide hydrolase (FAAH), led to discovery of a novel nicotinamide-based lead 12a having reversible mechanism of action. Focused SAR around the pyridine heterocycle (Ar) in 12a (Tables 1 and 2) resulted into four shortlisted compounds, (−)-12a, (−)-12i, (−)-12l–m. The required (−)-enantiomers were obtained via diastereomeric resolution of a novel chiral dissymmetric

  化学型PF-3845 / 04457845（一种基准标记的脂肪酸酰胺水解酶（FAAH）的不可逆抑制剂）中尿素部分的概念设计和修饰导致发现了一种新型的具有可逆作用机理的基于烟酰胺的铅12a。在12a中将SAR集中在吡啶杂环（Ar）周围（表1和2）（表1和表2），形成了四个候选化合物（-）- 12a，（-）- 12i，（-）- 12l – m。通过新型手性不对称中间体15的非对映异构体拆分获得所需的（-）-对映体。基于FAAH效力，在肝微粒体代谢稳定性的比较曲线，抑制主要hCYP450同种型，大鼠PK，和脑渗透能力的责任，二SAR优化化合物，（ - ） - 12升和（ - ） - 12米，被选择用于功效化疗诱发的周围神经病变（CIPN）大鼠模型的研究。当以3–30 mg / kg口服7天后，这两种化合物均显示出与剂量相关的抗痛觉过敏作用。30 mg / kg的作用与PF-04457845（10
• 咪唑并喹唑啉衍生物及其在抗肿瘤抗炎中的 应用
  申请人：浙江大学

  公开号：CN108383849B

  公开（公告）日：2020-11-06

  本发明提供一种作为PI3K抑制剂的咪唑并喹唑啉衍生物，所述化合物包括其类似物和其药学上可接受的盐、立体异构体、溶剂合物。本发明采用成环策略，对原有的Copanlisib的左侧部分进行合环和结构修饰，或在Copanlisib左侧氧原子上引入含氟片段Rf，优化分子的理化性质。实验表明所述化合物的药代动力学性质比Copanlisib有明显改善，分布容积显著降低，可降低药物在体内聚积的风险。这类化合物具有较好的药代动力学特性和较低的毒副作用，具有广阔的抗肿瘤和抗炎的应用前景，可在制备抗肿瘤、抗炎药物中的应用。所述化合物通式a和通式b结构：
• [EN] ALKOXY-SUBSTITUTED 2,3-DIHYDROIMIDAZO[1,2-C]QUINAZOLINES<br/>[FR] 2,3-DIHYDROIMIDAZO[1,2-C]QUINAZOLINES À SUBSTITUTION ALCOXY
  申请人：BAYER PHARMA AG

  公开号：WO2012062745A1

  公开（公告）日：2012-05-18

  The present invention relates to alkoxy-substituted 2,3-dihydroimidazo[1,2-c]quinazoline compounds of general formula (I) in which R1, R2 and R3 are as defined in the claims, to methods of preparing said compounds, to intermediates for the preparation of 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 a hyper-proliferative and/or angiogenesis disorder, as a sole agent or in combination with other active ingredients.

  本发明涉及一般式(I)中R1、R2和R3如权利要求中定义的烷氧基取代的2,3-二氢咪唑[1,2-c]喹唑啉化合物，以及制备所述化合物的方法，用于制备所述化合物的中间体，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，特别是治疗或预防高增殖和/或血管生成障碍的疾病，作为唯一药剂或与其他活性成分结合使用。
• Substituted imidazopyrimidine, imidazopyrazine and imidazopyridazine derivatives as melanocortin-4 receptor modulators
  申请人：Santhera Pharmaceuticals (Schweiz) AG

  公开号：EP2103614A1

  公开（公告）日：2009-09-23

  The present invention relates to substituted imidazopyrimidine derivatives, substituted imidazopyrazine derivatives and substituted imidazopyridazine derivatives as melanocortin-4 receptor (MC-4R) modulators, in particular as melanocortin 4 receptor antagonists. The antagonists are useful for the treatment of disorders and diseases such as cancer cachexia, muscle wasting, anorexia, emesis, anxiety, amytrophic lateral sclerosis and depression.

  本发明涉及取代咪唑吡啶衍生物、取代咪唑吡嗪衍生物和取代咪唑吡啶二嗪衍生物作为黑色素皮质素-4受体（MC-4R）调节剂，特别是作为黑色素皮质素4受体拮抗剂。这些拮抗剂可用于治疗癌症恶病质、肌肉消耗、厌食症、呕吐、焦虑、肌萎缩性侧索硬化和抑郁等疾病和疾病。