1,4-二氢-6-(甲硫基)-4-氧代-2-苯基-5-嘧啶甲腈 | 15908-64-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 1,4-二氢-6-(甲硫基)-4-氧代-2-苯基-5-嘧啶甲腈
• 中文别名: 4-(甲硫基)-6-羰基-2-苯基-1,6-二氢嘧啶-5-甲腈
• 英文名称: 6-Hydroxy-4-(methylthio)-2-phenylpyrimidin-5-carbonitril
• 英文别名: 4-hydroxy-6-(methylthio)-2-phenylpyrimidine-5-carbonitrile；4-(Methylthio)-6-oxo-2-phenyl-1,6-dihydropyrimidine-5-carbonitrile；4-methylsulfanyl-6-oxo-2-phenyl-1H-pyrimidine-5-carbonitrile
• CAS: 15908-64-2
• 化学式: C₁₂H₉N₃OS
• mdl: MFCD00067844
• 分子量: 243.289
• InChiKey: OUSBLYHTCSUCNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  90.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090

SDS

Name:	4-(Methylthio)-6-oxo-2-phenyl-1 6-dihydropyrimidine-5-carbonitrile Material Safety Data Sheet
Synonym:
CAS:	15908-64-2

Section 1 - Chemical Product MSDS Name:4-(Methylthio)-6-oxo-2-phenyl-1 6-dihydropyrimidine-5-carbonitrile Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
15908-64-2	4-(Methylthio)-6-oxo-2-phenyl-1,6-dihy	97+%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
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.
Notes to Physician:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 15908-64-2: Personal Protective Equipment Eyes: Not available.
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: 312 - 314 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H9N3OS
Molecular Weight: 243.29

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 15908-64-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(Methylthio)-6-oxo-2-phenyl-1,6-dihydropyrimidine-5-carbonitrile - 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
Shipping Name: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 15908-64-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 15908-64-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 15908-64-2 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：

  1,4-二氢-6-(甲硫基)-4-氧代-2-苯基-5-嘧啶甲腈 在 盐酸 、 sodium hydride 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 二甲基亚砜 为溶剂， 反应 7.0h， 生成 methyl 1-cyano-1-(5-cyano-4-methylthio-2-phenylpyrimidin-6-yl)acetate
  参考文献：
  名称：

  Kohra, Shinya; Tominaga, Yoshinori; Hosomi, Akira, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 959 - 968

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3-双(甲硫基)-2-氰基丙烯酸乙酯 、 苄脒盐酸盐 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以93%的产率得到1,4-二氢-6-(甲硫基)-4-氧代-2-苯基-5-嘧啶甲腈
  参考文献：
  名称：

  新型强效PDE4抑制剂5-氨基甲酰基-2-苯基嘧啶衍生物的合成及生物学评价

  摘要：

  5-氨基甲酰基-2-苯基嘧啶衍生物2被鉴定为具有中等PDE4B抑制活性（IC 50  = 200 nM）的磷酸二酯酶4（PDE4）抑制剂。的羧酸部分的修饰2得到Ñ -neopentylacetamide衍生物10f中，其具有在体外PDE4B抑制活性高（IC 50  = 8.3纳米）和体内抗内毒素效力（LPS）诱导的中性粒细胞增多肺小鼠（ID 50  = 16毫克/千克，ip）。此外，基于与人类PDE4B催化域结合的10f的X射线晶体学，我们设计了7,8-dihydro-6 H -pyrido [4,3- d] pyrimidin-5-one衍生物39，其具有稠合的双环内酰胺支架。化合物39对小鼠脾细胞中LPS诱导的肿瘤坏死因子α（TNF-α）的产生表现出优异的抑制活性（IC 50  = 0.21 nM），对小鼠LPS诱导的肺嗜中性粒细胞具有体内抗炎活性（在时抑制41％）剂量为1.0 mg /

  DOI：

  10.1016/j.bmc.2013.09.013

文献信息

• A convenient synthesis of pyrimidinone and pyrimidine containing bisheteroarenes and analogs
  作者：Hardesh K. Maurya、Atul Gupta

  DOI：10.1039/c4ra01689k

  日期：——

  The synthesis of pyrimidinone containing bisheteroarenes (3) and related analogs (9 and 10) by the reaction of active methylenes or substituted methyl acrylate with nitrogen containing precursors viz. amidines, or thiourea in water as well as other organic solvents was studied. Synthesized compounds have further been explored for the synthesis of diversified pyrimidines 4, 6–8, 11, 12 and 14 through

  通过活性亚甲基或取代的丙烯酸甲酯与含氮前体的反应合成含双嘧啶酮的嘧啶酮（3）和相关类似物（9和10）。water以及其他有机溶剂中的或硫脲进行了研究。合成的化合物已进一步探讨了多元化嘧啶的合成4，6-8，11，12和14通过一个顺序方法。
• New heterocyclic compounds
  申请人：Sharma Ganapavarapu V.R.

  公开号：US20080221103A1

  公开（公告）日：2008-09-11

  Provided herein are heterocyclic compounds of the general formula (I), their derivatives, analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts and compositions, metabolites and prodrugs thereof, wherein R 1 , R 2 , R 3 , R 4 and R 5 are as described herein. Further described herein in particular are heterocyclic compounds of the formula (I) for treating various diseases. and disorders by administering in a patient one or more TNF-α, Thromboxane synthase, 5-LOX, and PDE4 inhibitors. In particular described herein are methods for treating immunological diseases, inflammation, pain disorder, rheumatoid arthritis; osteoporosis; multiple myeloma; uveititis; acute and chronic myelogenous leukemia; ischemic heart disease; atherosclerosis; cancer; ischemic-induced cell damage; pancreatic beta cell destruction; osteoarthritis; rheumatoid spondylitis; gouty arthritis; inflammatory bowel disease; adult respiratory distress syndrome (ARDS); psoriasis; Crohn's disease; allergic rhinitis; ulcerative colitis; anaphylaxis; contact dermatitis; muscle degeneration; cachexia; asthma; bone resorption diseases; ischemia reperfusion injury; brain trauma; multiple sclerosis; sepsis; septic shock; toxic shock syndrome; fever, and myalgias due to infection and diseases mediated by HIV-1; HIV-2; HIV-3; cytomegalovirus (CMV); influenza; adenovirus; the herpes viruses (including HSV-1, HSV-2) and herpes zoster viruses in a mammal comprising administering an effective amount of a compound of formula (I).

  本文提供了一般式(I)的杂环化合物，它们的衍生物、类似物、互变异构体、立体异构体、多晶形态、水合物、溶剂合物、药学上可接受的盐和组合物、代谢产物及其前药，其中R1、R2、R3、R4和R5如本文所述。特别在此描述了一般式(I)的杂环化合物，用于治疗各种疾病和疾病，通过在患者中给予一种或多种TNF-α、血栓素合成酶、5-LOX和PDE4抑制剂。特别在此描述了治疗免疫性疾病、炎症、疼痛障碍、类风湿性关节炎；骨质疏松症；多发性骨髓瘤；葡萄膜炎；急性和慢性骨髓性白血病；缺血性心脏病；动脉粥样硬化；癌症；缺血性细胞损伤；胰岛素β细胞破坏；骨关节炎；类风湿脊柱炎；痛风性关节炎；炎症性肠病；成人呼吸窘迫综合症（ARDS）；银屑病；克罗恩病；过敏性鼻炎；溃疡性结肠炎；过敏性休克；接触性皮炎；肌肉退化；虚弱症；哮喘；骨吸收疾病；缺血再灌注损伤；脑外伤；多发性硬化；败血症；脓毒性休克；中毒性休克综合征；发热，以及由HIV-1；HIV-2；HIV-3；巨细胞病毒（CMV）；流感病毒；腺病毒；单纯疱疹病毒（包括HSV-1、HSV-2）和带状疱疹病毒介导的感染和疾病在哺乳动物中，包括给予一种一般式(I)化合物的有效剂量。
• A Novel One-Pot Method for the Synthesis of Pyrimidine Derivatives Using Ketene N,S-Acetal with Aryl Aldehydes
  作者：Masayori Hagimori、Yuka Murakami、Naoko Mizuyama、Yoshinori Tominaga

  DOI：10.1002/jhet.2397

  日期：2016.1

  A very simple and facile one‐pot method for the synthesis of pyrimidine derivatives is presented. In this method, 2‐aryl‐pyrimidine derivatives were prepared by the reaction of ketene N,S‐acetal 1 with commercially available aryl aldehydes by heating under solvent and catalyst‐free conditions. The synthesized pyrimidine derivatives showed blue‐green fluorescence in solid state.

  提出了一种非常简单，简便的嘧啶衍生物合成方法。在这种方法中，通过在无溶剂和无催化剂的条件下加热，使烯酮N，S-乙缩醛1与市售的芳基醛反应，可以制备2-芳基-嘧啶衍生物。合成的嘧啶衍生物呈固态呈蓝绿色荧光。
• Richter, Monika; Vogt, Almut; Augustin, Manfred, Zeitschrift fur Chemie, 1989, vol. 29, # 12, p. 443 - 444
  作者：Richter, Monika、Vogt, Almut、Augustin, Manfred、Strauss, Karin

  DOI：——

  日期：——
• Ram, Vishnu J; Haque, Navedul; Nath, Mahendra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 7, p. 754 - 759
  作者：Ram, Vishnu J、Haque, Navedul、Nath, Mahendra

  DOI：——

  日期：——