1,3-二甲基-5-硝基尿嘧啶水合物 | 41613-26-7

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 1,3-二甲基-5-硝基尿嘧啶水合物
• 中文别名: 1,3-二甲基-5-硝基尿嘧啶单水合物
• 英文名称: 1,3-dimethyl-5-nitrouracil
• 英文别名: 5-Nitro-1,3-dimethyl-uracil；1,3-dimethyl-5-nitropyrimidine-2,4(1H,3H)-dione；1,3-dimethyl-5-nitropyrimidine-2,4-dione
• CAS: 41613-26-7
• 化学式: C₆H₇N₃O₄
• mdl: MFCD00023800
• 分子量: 185.139
• InChiKey: SDLBIQNBDPOOPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  155-160 °C(lit.)
• 沸点：
  262.7±43.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25,S26,S36/37
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933599090
• 储存条件：
  存放于0至6℃阴凉干燥处。

SDS

Name:	1 3-Dimethyl-5-Nitrouracil Monohydrate Material Safety Data Sheet
Synonym:	None
CAS:	41613-26-7

Section 1 - Chemical Product MSDS Name:1 3-Dimethyl-5-Nitrouracil Monohydrate Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
41613-26-7	1,3-Dimethyl-5-Nitrouracil Monohydrate	100	255-462-8

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. Wash clothing before reuse.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid if cough or other symptoms appear.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide. Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Wash hands before eating. Use with adequate ventilation. Minimize dust generation and accumulation.
Avoid breathing dust, vapor, mist, or gas. Do not get on skin or in eyes. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 41613-26-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 155 - 157 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H7N3O4.H2O
Molecular Weight: 203.16

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 41613-26-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,3-Dimethyl-5-Nitrouracil Monohydrate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 41613-26-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 41613-26-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 41613-26-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,3-二甲基-5-硝基尿嘧啶水合物 在 双氧水 作用下， 生成 5-hydroxy-1,3-dimethylimidazolidine-2,4-dione
  参考文献：
  名称：

  Dehydrogenation, oxidative denitration and ring contraction of N,N-dimethyl-5-nitrouracil by a Bacillus nitroreductase Nfr-A1

  摘要：

  Nfr-A1, a Bacillus subtilis nitroreductase, catalyzes the nitroreduction of a large panel of aromatic and heterocyclic nitro compounds, except those belonging to nitrouracil class of molecules. Besides nitroreduction, Nfr-A1 exhibits a strong NADH oxidase activity in the presence of oxygen, leading to high concentration of H2O2 (up to 200 mu M). In the presence of (N,N)-dimethyl-5-nitrouracil 1 (dim-NU), Nfr-A1 achieves the reduction of dim-NU double bond to compounds 2 and 3 and in parallel the oxidation of dim-NU to the denitrated five membered derivatives 4 and 5. The reduction is catalyzed by the reduced Flavin Fl-(Red) and resembles those catalyzed by dihydropyrimidine clehydrogenases (DPD), during the catabolism of pyrimidines. The oxidative denitration is catalyzed in part by hydrogen peroxide generated through the NADH-oxidase activity, and certainly by the peroxyflavin intermediate Fl-(OOH) for the other part. The mechanisms of reaction were proposed according to experimental data and literature. These findings together with our previous results on the potential biological role of Nfr-A1, confirm the large spectrum of catalysis supported by this enzyme. The oxidative denitration is sporadically reported in literature and represents a safe and green alternative for the remediation of nitro-compounds. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.11.014
• 作为产物：
  描述：

  3-methyl-5-nitro-1-phenyluracil 在 硝酸 作用下， 以 甲醇 、 硫酸 为溶剂， 反应 1.0h， 生成 1,3-二甲基-5-硝基尿嘧啶水合物
  参考文献：
  名称：

  在5位上具有吸电子基团的尿嘧啶衍生物与胺的新反应：尿嘧啶N 1部分与胺之间的交换反应

  摘要：

  具有在5-位的吸电子基团例如硝基，氨基甲酰基和氰基的1，3-二取代的尿嘧啶与伯胺的反应导致尿嘧啶环的N 1部分与胺部分交换。交换反应受5-和N 1-位上取代基的性质影响。用加成，开环和闭环的方式解释反应顺序。

  DOI：

  10.1039/p19900000367

文献信息

• [EN] FUSED PYRIMIDINE-DIONE DERIVATIVES AS TRPA1 MODULATORS<br/>[FR] DÉRIVÉS DE PYRIMIDINEDIONES FUSIONNÉS UTILISÉS COMME MODULATEURS DES RÉCEPTEURS TRPA1
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2010109287A1

  公开（公告）日：2010-09-30

  The invention described herein relates to novel fused pyrimidinediones derivatives of formula (I) which are TRPA (Transient Receptor Potential subfamily A) modulators. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by TRPAl (Transient Receptor Potential subfamily A, member 1). This invention also provides processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders modulated by TRPAl. Formula (I)

  本发明描述的是一类新颖的杂合吡啶二酮衍生物，其化学公式为（I），这些衍生物是TRPA（瞬时受体电位亚家族A）的调节剂。特别是，本文所述的化合物对于治疗或预防由TRPA1（瞬时受体电位亚家族A成员1）调控的疾病、状况和/或失调是有用的。本发明还提供了制备所述化合物、它们合成中使用的中间体、药物组合物以及治疗或预防由TRPA1调控的疾病、状况和/或失调的方法。公式（I）
• [EN] IMIDAZOPYRROLIDINONE COMPOUNDS<br/>[FR] COMPOSÉS IMIDAZOPYRROLIDINONE
  申请人：NOVARTIS AG

  公开号：WO2013111105A1

  公开（公告）日：2013-08-01

  The invention relates to compounds of formula (I): (I) as described herein, pharmaceutical preparations comprising such compounds, uses and methods of use for such compounds in the treatment of a disorder or a disease mediated by the activity of MDM2 and/or MDM4, and combinations comprising such compounds.

  这项发明涉及式(I)的化合物：(I)如本文所述，包括这种化合物的药物制剂，以及在治疗由MDM2和/或MDM4活性介导的疾病或疾病中使用这种化合物的用途和方法，以及包含这种化合物的组合物。
• Effect of the 6-Methyl Group on Peroxyl Radical Trapping by 5-Hydroxyand 5-Amino- Derivatives of 1,3-Dimethyluracil
  作者：Stanislav Grabovskiy、Arcadiy Antipin、Yulia Grabovskaya、Nadezhda Andriayshina、Oksana Akchurina、Natalie Kabal'nova

  DOI：10.2174/1570178614666161121123024

  日期：2017.2.13

  Background: Many synthetic and natural uracil derivatives have biological activity. Furthermore, many of these derivatives have pro- and antioxidant properties, but the mechanism of these processes is far from being understood. Methods: Oxygen-uptake kinetics and computational methods (CBS-QB3, M062X/MG3S and SMDM05/ MG3S) were combined to study the reaction of peroxyl radicals with five organic-soluble derivatives: 5-amino- and 5-hydroxy-1,3-dimethyluracil, 5-amino- and 5-hydroxy-1,3,6-trimethyluracil, and 5-hydroxy-1,3-dimethyl-6-phenyluracil in chlorobenzene. Results: The studied uracil derivatives should be classified as inhibitors of medium reactivity kin = (1-10) × 10-4 M-1 s-1. The methyl group in the 6-position of the pyrimidine ring increases the rate constant of the reaction with peroxyl radicals by 3-4 times and the stoichiometric coefficient of inhibition. The calculation of the reaction barrier heights at the SMD-M05/MG3S level of theory for the hydrogen abstraction is in good agreement with experimental data. Conclusion: 1,3-Dimethyl-5-aminouracil is transformed by the addition of a methyl group at the 6-position into a favic-like pyrimidine, while the 5-hydroxy derivative becomes a more effective antioxidant. The bound dissociation energy (O-H or N-H) and the IP for the reactivity forecasting of uracil derivatives were used, but it was found that this methodology did not lead to good correlation between experimental and theoretical results. The SMD-M05/MG3S method provided the most accurate calculations of the reaction barrier heights for hydrogen abstraction from uracil derivatives by peroxyl radical.

  背景：许多合成和天然的尿嘧啶衍生物具有生物活性。此外，这些衍生物中的许多具有促进氧化和抗氧化特性，但其作用机制远未被理解。 方法：结合氧摄取动力学和计算方法（CBS-QB3、M062X/MG3S 和 SMDM05/MG3S）研究了过氧自由基与五种有机可溶性衍生物的反应：5-氨基和5-羟基-1,3-二甲基尿嘧啶、5-氨基和5-羟基-1,3,6-三甲基尿嘧啶，以及5-羟基-1,3-二甲基-6-苯基尿嘧啶在氯苯中的反应。 结果：所研究的尿嘧啶衍生物应归类为中等反应活性抑制剂，反应速率常数kin = (1-10) × 10-4 M-1 s-1。嘧啶环的6位甲基增加了与过氧自由基反应的速率常数3-4倍，并增加了抑制的化学计量系数。在SMD-M05/MG3S理论水平上对氢抽提反应势垒高度的计算与实验数据吻合良好。 结论：1,3-二甲基-5-氨基尿嘧啶通过在6位添加一个甲基，转化为类似favic的嘧啶，而5-羟基衍生物则成为更有效的抗氧化剂。使用了结合解离能（O-H或N-H）和IP来进行尿嘧啶衍生物反应性的预测，但发现这种方法并未导致实验和理论结果之间的良好相关性。SMD-M05/MG3S方法为过氧自由基从尿嘧啶衍生物中抽提氢的反应提供了最准确的势垒高度计算。
• Nitration of Aromatic Heterocycles with Palladium(II) Acetate and Sodium Nitrite
  作者：Toshio Itahara、Reiko Ebihara、Kazukuni Kawasaki

  DOI：10.1246/bcsj.56.2171

  日期：1983.7

  Treatments of 1,3-dimethyluracil, 1-methyl-2-pyridone, and thiophene with palladium(II) acetate and sodium nitrite gave the corresponding nitro-substituted products.

  用乙酸钯 (II) 和亚硝酸钠处理 1,3-二甲基尿嘧啶、1-甲基-2-吡啶酮和噻吩，得到相应的硝基取代产物。
• [EN] PYRROLO[3,2-D]PYRIMIDINE-2,4(3H,5H)-DIONE DERIVATIVES<br/>[FR] DÉRIVÉS DE PYRROLO[3,2-D]PYRIMIDINE-2,4(3H,5H)-DIONE
  申请人：HYDRA BIOSCIENCES INC

  公开号：WO2016023831A1

  公开（公告）日：2016-02-18

  This invention relates to novel Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione derivatives of Formula (I), and their use as TRPC5 modulators, pharmaceutical compositions containing the same, and methods of using the same as agents for the treatment of TRPC5 receptor mediated disorders or conditions. R1, R2, R3 R4 and R5 have meanings given in the description.

  本发明涉及一种新型的Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-二酮衍生物，其化学式为（I），以及它们作为TRPC5调节剂的用途，含有这些化合物的药物组合物，以及将其用作治疗TRPC5受体介导的疾病或症状的药物的方法。R1、R2、R3、R4和R5的含义见描述。

表征谱图