6-氨基-1-丙基尿嘧啶 | 53681-47-3

• 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 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-氨基-1-丙基尿嘧啶
• 英文名称: 6-amino-1-propyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-propyl-6-aminouracil；6-amino-1-propylpyrimidine-2,4(1H,3H)-dione；6-amino-1-n-propyl-1,3-dihydropyrimidine-2,4-dione；6-Amino-1-propyluracil；6-amino-1-propylpyrimidine-2,4-dione
• CAS: 53681-47-3
• 化学式: C₇H₁₁N₃O₂
• mdl: MFCD00075365
• 分子量: 169.183
• InChiKey: KTWOUYVBZDZRNV-UHFFFAOYSA-N

物化性质

• 熔点：
  279-281℃
• 密度：
  1.212±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090
• 储存条件：
  存放于室温环境，避光保存，并在惰性气体氛围中保持稳定性。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Amino-1-propyl-3H-pyrimidine-2,4-dione
Synonyms: 6-Amino-1-propyluracil

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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: 6-Amino-1-propyl-3H-pyrimidine-2,4-dione
CAS number: 53681-47-3

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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: C7H11N3O2
Molecular weight: 169.2

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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

制备方法与用途

6-氨基-1-丙基尿嘧啶是一种用于制备己酮可可碱代谢物类似物，进而作为抗炎药物反应物的物质。

反应信息

• 作为反应物：
  描述：

  6-氨基-1-丙基尿嘧啶 在 2,2'-联吡啶 、 sodium dithionite 、 copper diacetate 、 sodium carbonate 、 溶剂黄146 、 三乙胺 、 碳酸二甲酯 、 sodium hydroxide 、 sodium nitrite 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 8-(6-chloropyridin-3-yl)-1-cyclopropyl-3-propyl-3,7-dihydropurine-2,6-dione
  参考文献：
  名称：

  METHODS FOR THE SYNTHESIS OF 1,3-SUBSTITUTED AMINOURACILS AND OTHER XANTHINE-RELATED COMPOUNDS

  摘要：

  提供了合成二取代氨基尿嘧啶和黄嘌呤和/或相关化合物的方法。

  公开号：

  US20130324724A1
• 作为产物：
  描述：

  2-氰基-N-[(丙基氨基)羰基]乙酰胺 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以28.9g的产率得到6-氨基-1-丙基尿嘧啶
  参考文献：
  名称：

  基于结构的黄嘌呤-苯并咪唑衍生物作为新型强效色氨酸羟化酶抑制剂的设计

  摘要：

  色氨酸羟化酶催化血清素合成的第一步和限速步骤。5-羟色胺是中枢神经系统中的一种关键神经递质，在外周，作为具有多种生理功能的局部激素发挥作用。对转基因小鼠模型的研究表明，外周血清素水平的失调会导致代谢、炎症和纤维化疾病。肿瘤细胞过度产生血清素会导致类癌综合征典型的严重症状，色氨酸羟化酶抑制剂已经在临床上用于患有这种疾病的患者。在这里，我们描述了一类新的强效色氨酸羟化酶抑制剂，其特征在于跨越所有对催化重要的活性结合位点，特别是那些共底物蝶呤，底物色氨酸以及直接螯合催化铁离子。这些抑制剂旨在有效减少外周的血清素，同时不通过血脑屏障，从而保持大脑中的血清素水平。

  DOI：

  10.1021/acs.jmedchem.2c00598

文献信息

• Immunosuppressive effects of 8-substituted xanthine derivatives
  申请人：K.U. Leuven Research & Development

  公开号：US07253176B1

  公开（公告）日：2007-08-07

  The invention relates to a novel use of 8-substituted xanthine derivatives for the manufacture of a medicament for the treatment of auto-immuno disorders.

  这项发明涉及使用8-取代黄嘌呤衍生物制造治疗自身免疫性疾病药物的新方法。
• Compounds for inhibition of ceramide-mediated signal transduction
  申请人：The Regents of the University of California

  公开号：US20020165202A1

  公开（公告）日：2002-11-07

  Novel, heterocyclic compounds having at least one ring nitrogen, disclosed side chains and, in some embodiments, an oxygen ortho to the ring nitrogen inhibit inflammatory responses associated with TNF-&agr; and fibroblast proliferation in vivo and in vitro. The compounds of the invention neither appreciably inhibit the activity of cAMP phosphodiesterase nor the hydrolysis of phosphatidic acid, and are neither cytotoxic nor cytostatic. Preferred compounds of the invention are esters. Methods for the use of the novel compounds to inhibit ceramide-mediated intracellular responses in stimuli in vivo (particularly TN-&agr;) are also described. The methods are expected to be of use in reducing inflammatory responses (for example, after angioplasty), in limiting fibrosis (for example, of the liver in cirrhosis), in inhibiting cell senescence, cell apoptosis and UV induced cutaneous immune suppression. Compounds having enhanced water solubility are also described.

  新颖的、至少含有一个环状氮的杂环化合物，揭示了侧链，并在某些实施例中，对抗与TNF-α和成纤维细胞增殖有关的炎症反应，无论在体内还是体外。本发明的化合物既不显著抑制cAMP磷酸二酯酶的活性，也不抑制磷脂酸的水解，既不具有细胞毒性，也不具有细胞毒性。本发明的优选化合物是酯类。还描述了使用这些新颖化合物来抑制体内（特别是TN-α）刺激介导的神经酰胺内细胞反应的方法。这些方法预计可用于减少炎症反应（例如在血管成形术后）、限制纤维化（例如在肝硬化中的肝脏）、抑制细胞衰老、细胞凋亡和紫外诱导的皮肤免疫抑制。还描述了具有增强水溶性的化合物。
• Substituted Xanthines, Pteridinediones, and Related Compounds as Potential Antiinflammatory Agents. Synthesis and Biological Evaluation of Inhibitors of Tumor Necrosis Factor α
  作者：Howard B. Cottam、Hsiencheng Shih、Lida R. Tehrani、D. Bruce Wasson、Dennis A. Carson

  DOI：10.1021/jm940845j

  日期：1996.1.1

  approximately 5 microM for each. Compound 58 was a very poor inhibitor of PDE IV but was the most active at preventing the leukopenia induced by TNF alpha in mice, providing more than 60% protection at 50 mg/kg. Thus, compounds such as 58, which are good inhibitors of TNF alpha production but are devoid of PDE IV inhibitory properties, may have potential as new antiinflammatory agents.

  在嘌呤，蝶啶，[1,2,5]-噻二唑并[3,4-d]嘧啶和喹唑啉环系统中制备了一系列己酮可可碱代谢物的类似物，并评估了它们抑制肿瘤坏死因子产生的能力。细菌脂多糖（LPS）刺激的人外周血单核细胞中的α-α（TNFα）。还测试了更具活性的化合物对人嗜中性白细胞对环状AMP磷酸二酯酶IV型（PDE IV）的抑制作用，以帮助确定其作用机理。在小鼠体内LPS诱导的白细胞减少症模型中评估了在体外TNFα测定中显示出良好活性的所选化合物。TNFα分析中最有效的化合物6、31和58，每种抑制TNFα的产生，IC50约为5 microM。化合物58是一种非常差的PDE IV抑制剂，但在预防小鼠中由TNFα诱导的白细胞减少症中活性最高，在50 mg / kg剂量下可提供60％以上的保护作用。因此，诸如58的化合物，它们是TNFα产生的良好抑制剂，但没有PDE IV抑制特性，可能具有作为新的抗炎剂的潜力。
• 3,8-Dialkylxanthines
  申请人：Aktiebolaget Draco

  公开号：US04546182A1

  公开（公告）日：1985-10-08

  The invention refers to compounds having activity against chronic obstructive airway disease or cardiovascular disease, characterized by the formula ##STR1## wherein R.sup.1 is ethyl, n-propyl, n-butyl, isobutyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexylmethyl, and R.sup.2 is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert. butyl, or cyclobutyl provided that R.sup.1 is ethyl when R.sup.2 is methyl, or a physiologically acceptable salt thereof. The invention also refers to processes for the preparation of these compounds, a pharmaceutical preparation containing one of the compounds and a method for the treatment of chronic obstructive airway disease and cardiovascular disease.

  本发明涉及对慢性阻塞性呼吸道疾病或心血管疾病具有活性的化合物，其特征在于公式##STR1##，其中R.sup.1是乙基，正丙基，正丁基，异丁基，正戊基，2-甲基丁基，3-甲基丁基，2,2-二甲基丙基，环丙基，环丁基，环戊基或环己基甲基，R.sup.2是甲基，乙基，正丙基，异丙基，环丙基，正丁基，异丁基，叔丁基或环丁基，条件是当R.sup.2是甲基时，R.sup.1是乙基，或其生理可接受的盐。本发明还涉及这些化合物的制备方法，含有一种化合物的药物制剂以及治疗慢性阻塞性呼吸道疾病和心血管疾病的方法。
• Construction of Dihydropyrido[2,3-<i>d</i>]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by <i>N</i>-Heterocyclic Carbenes
  作者：Krzysztof Dzieszkowski、Izabela Barańska、Zbigniew Rafiński

  DOI：10.1021/acs.joc.0c00657

  日期：2020.5.15

  N-Heterocyclic carbenes (NHCs) catalyzing aza-Claisen rearrangement of α,β-unsaturated enals with cyclic vinylogous amides under oxidative conditions generating potentially biologically active dihydropyridinone-fused uracils have been developed. This strategy represents a unique NHC-activation-based path with the use of 6-aminouracils as stable α,β-diEWG cyclic vinylogous amides for the efficient synthesis

  已经开发了在氧化条件下用环乙烯基乙烯基酰胺催化α，β-不饱和烯醛的氮杂-碳烯化合物（NHC）催化a，β-不饱和烯醛的氮杂-克莱森重排的方法，该方法可合成具有潜在生物活性的二氢吡啶并酮融合的尿嘧啶。该策略代表了独特的基于NHC活化的途径，使用6-氨基尿嘧啶作为稳定的α，β-diEWG环状乙烯基酰胺，可有效合成双环N-未保护的内酰胺，类似于许多有用药物中的内酰胺。