2,4-喹唑啉二酮 | 86-96-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2,4-喹唑啉二酮
• 中文别名: 苯并四氢嘧啶-2,4-二酮；硫化氢氨钾；2,4(1H,3H)-喹唑啉二酮；2,4-二羟基喹唑啉；亚苯甲酰基脲；2,4(1H,3H)-喹唑二酮；伸苯甲醯尿；喹唑啉-2,4-二酮
• 英文名称: 1,2,3,4-tetrahydro-quinazoline-2,4-dione
• 英文别名: 1H-quinazoline-2,4-dione；quinazoline-2,4(1H,3H)-dione；benzoyleneurea；quinazoline-2,4-dione；1,3-dihydroquinazoline-2,4-dione
• CAS: 86-96-4
• 化学式: C₈H₆N₂O₂
• mdl: MFCD00006699
• 分子量: 162.148
• InChiKey: SDQJTWBNWQABLE-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C(lit.)
• 沸点：
  288.82°C (rough estimate)
• 密度：
  1.3264 (rough estimate)
• 溶解度：
  氢氧化铵：可溶10mg/mL
• 最大波长(λmax)：
  217nm(EtOH)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  2
• 海关编码：
  2933990090
• RTECS号：
  VA1390000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  避光，密闭保存。

SDS

Name:	Benzoyleneurea Material Safety Data Sheet
Synonym:	2,4(1H,3H)-Quinazolinedion
CAS:	86-96-4

Section 1 - Chemical Product MSDS Name:Benzoyleneurea Material Safety Data Sheet
Synonym:2,4(1H,3H)-Quinazolinedion

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
86-96-4	Benzoyleneurea		201-712-6

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
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.
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:
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 86-96-4: 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: Powder
Color: light pink
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 300 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: C8H6N2O2
Molecular Weight: 162.15

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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.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 86-96-4: VA1390000 LD50/LC50:
CAS# 86-96-4: Oral, mouse: LD50 = >3 gm/kg.
Carcinogenicity:
Benzoyleneurea - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 86-96-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 86-96-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 86-96-4 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

制备方法与用途

生物活性

Benzoyleneurea 具有抗菌活性，并常被用作合成新型 PGGTase-I 抑制剂的支架。

化学性质

Benzoyleneurea 为白色针状晶体，熔点为300℃。它可溶于醇类物质，而不溶于水。

用途

Benzoyleneurea 主要用作有机合成中间体。

反应信息

• 作为反应物：
  描述：

  2,4-喹唑啉二酮 在 盐酸 、 三正丙胺 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 N-(2-methoxyphenyl)-2-(piperazin-1-yl)quinazolin-4-amine
  参考文献：
  名称：

  Discovery of novel potent and selective ligands for 5-HT2A receptor with quinazoline scaffold

  摘要：

  A series of compounds with quinazoline scaffold were designed, synthesized and evaluated as novel potent 5-HT2A receptor ligands. N-(4-Chlorophenyl)-2-(piperazin-1-yl)quinazolin-4-amine (5o) has a K-i value of 14.04 +/- 0.21 nM, with a selectivity more than 10,000 fold over 5-HT1A receptors (D-1 and D-2-like receptors). The functional assay showed that this compound is an antagonist to 5-HT2A receptor with an IC50 value of 1.66 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.030
• 作为产物：
  描述：

  2-氨基苯甲腈 在 二氧化碳 、 C₅H₁₄NO⁽¹⁺⁾*C₅H₄NO^(1-) 作用下， 80.0 ℃ 、100.0 kPa 条件下， 反应 9.0h， 以92.3%的产率得到2,4-喹唑啉二酮
  参考文献：
  名称：

  一种制备 2,4-（1H, 3H）-喹唑啉二酮类化合物的方法

  摘要：

  本发明公开了一种制备2,4‑（1H,3H）‑喹唑啉二酮类化合物的方法，它以式（1）所示的2‑氨基苯甲氰类化合物和二氧化碳为原料，在2‑羟基吡啶型离子液体中反应得到式（II）所示的2,4‑（1H,3H）‑喹唑啉二酮类化合物，其反应式如下：。本发明的离子液体在应用于制备2,4‑（1H,3H）‑喹唑啉二酮类化合物的反应中时，反应条件较为温和，产物的分离纯化过程较为简单，产物产率高，底物适用范围广。

  公开号：

  CN112778219A
• 作为试剂：
  描述：

  、 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole tosylate 、 2,4-喹唑啉二酮 、 氢氧化钾 在 甲醇 、 2,4-喹唑啉二酮 、 crude solution 、 水 、 N,N-二甲基甲酰胺 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 、 甲苯 为溶剂， 反应 4.0h， 以to give 3-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-2,4-(1H,3H)quinazolinedione melting at about 261°-264° C.的产率得到3-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-1H-quinazoline-2,4-dione
  参考文献：
  名称：

  N-[2-(nitro-1-imidazolyl)ethyl]naphthal imides

  摘要：

  本文描述了一种具有硝基咪唑乙基基团作为N-取代基的咪唑类化合物。它们是抗菌和抗原虫剂。这些化合物是通过将适当的酰亚胺与氯乙基咪唑或相应的羟乙基化合物的tosylate或mesylate反应而制备的。

  公开号：

  US03997572A1

文献信息

• Quinazolines. 4*. Acylation of quinazoline-2,4-diones with aromatic acids chlorides in the presence of ferric chloride hexahydrate
  作者：R. Sh. Kuryazov、Yu. R. Takhirov、D. A. Dushamov、N. S. Mukhamedov、K. K. Turgunov、Kh. M. Shakhidoyatov、B. Tashkhodjaev

  DOI：10.1007/s10593-011-0675-6

  日期：2011.2

  The interaction of quinazoline-2,4-diones with aromatic acids chlorides in nitrobenzene has been investigated in the presence of FeCl3·6H2O. Optimum conditions for the acylation reaction have been developed, the used 4-substituted benzoyl chlorides have been put in order of relative activity, depending on the degree of their electrophilicity.

  在FeCl 3 ·6H 2 O存在的条件下，研究了喹唑啉-2,4-二酮与芳香族酰氯在硝基苯中的相互作用。研究了酰化反应的最佳条件，并提出了所用的4-取代的苯甲酰氯。相对活性的顺序，取决于它们的亲电程度。
• Synthesis and characterization of the first inhibitor of<i>N</i>-acylphosphatidylethanolamine phospholipase D (NAPE-PLD)
  作者：Beatrice Castellani、Eleonora Diamanti、Daniela Pizzirani、Piero Tardia、Martina Maccesi、Natalia Realini、Paola Magotti、Gianpiero Garau、Thomas Bakkum、Silvia Rivara、Marco Mor、Daniele Piomelli

  DOI：10.1039/c7cc07582k

  日期：——

  (NAPE-PLD) is a membrane-associated zinc enzyme that catalyzes the hydrolysis of N-acylphosphatidylethanolamines (NAPEs) into fatty acid ethanolamides (FAEs). Here, we describe the identification of the first small-molecule NAPE-PLD inhibitor, the quinazoline sulfonamide derivative 2,4-dioxo-N-[4-(4-pyridyl)phenyl]-1H-quinazoline-6-sulfonamide, ARN19874.

  Ñ -Acylphosphatidylethanolamine磷脂酶d（NAPE-PLD）是一种膜相关的，其催化水解酶锌Ñ -acylphosphatidylethanolamines（NAPEs）转换成脂肪酸乙醇酰胺（的FAE）。在这里，我们描述了第一个小分子NAPE-PLD抑制剂，喹唑啉磺酰胺衍生物2,4-二氧代-N- [4-（4-吡啶基）苯基] -1 H-喹唑啉-6-磺酰胺，ARN19874的鉴定。
• QUINAZOLINE-2,4-DIONE DERIVATIVES
  申请人：Hubschwerlen Christian

  公开号：US20140171425A1

  公开（公告）日：2014-06-19

  The invention relates to antibacterial compounds of formula (I), wherein R 1 is H, halogen, (C 1 -C 3 )alkyl or (C 1 -C 3 )alkoxy; R 2 is H, halogen, (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy or pyrrolidin-1-yl; R 3 is H, halogen, (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy, vinyl or 2-methoxycarbonyvinyl or R 2 and R 3 together with the two carbon atoms which bear them form a phenyl ring; R 4 is H, halogen, (C 1 -C 3 )alkyl or (C 1 -C 3 )alkoxy; and R 5 is H, (C 1 -C 3 )alkyl or cyclopropyl, or R 4 and R 5 form together a —CH 2 CH 2 CH 2 — group; A is the divalent group —CH 2 —, —CH 2 CH 2 —, #—CH(OH)CH 2 —*, #—CH 2 N(R 6 )—* and —CH 2 NHCH 2 —, wherein # indicates the point of attachment to the optionally substituted (quinazoline-2,4-dione-3-yl)methyl residue and * represents the point of attachment to the substituted (oxazolidinon-4-yl)methyl residue; R 6 is H or acetyl; Y is CH or N; and Q is O or S; and salts of such compounds.

  该发明涉及式(I)的抗菌化合物，其中R1为H、卤素、(C1-C3)烷基或(C1-C3)氧烷；R2为H、卤素、(C1-C3)烷基、(C1-C3)氧烷或吡咯烷-1-基；R3为H、卤素、(C1-C3)烷基、(C1-C3)氧烷、乙烯基或2-甲氧羰基乙烯基，或R2和R3与携带它们的两个碳原子一起形成苯环；R4为H、卤素、(C1-C3)烷基或(C1-C3)氧烷；R5为H、(C1-C3)烷基或环丙基，或R4和R5一起形成一个—CH2CH2CH2—基团；A为二价基团—CH2—、—CH2CH2—、#—CH(OH)CH2—*、#—CH2N(R6)—*和—CH2NHCH2—，其中#表示可选择取代的(喹唑啉-2,4-二酮-3-基)甲基残基的连接点，*表示取代的(噁唑烷酮-4-基)甲基残基的连接点；R6为H或乙酰基；Y为CH或N；Q为O或S；以及这类化合物的盐。
• Npy antagonists, preparation and uses
  申请人：Botez Iuliana

  公开号：US20090233910A1

  公开（公告）日：2009-09-17

  The present invention concerns novel compounds, their preparation and their uses, therapeutic uses in particular. More specifically it concerns derivative compounds having at least two aromatic cycles, their preparation and their uses, in particular in the area of human or animal health. These compounds have an affinity for the biological receptors of neuropeptide Y, NPY, present in the central and peripheral nervous systems. The compounds of the invention are preferably NPY antagonists, and more particularly antagonists of sub-type NPY Y1, and can therefore be used for the therapeutic or prophylactic treatment of any disorder involving NPY. The present invention also concerns pharmaceutical compositions containing said compounds, their preparation and their uses, as well as treatment methods using said compounds.

  本发明涉及新颖化合物，它们的制备和用途，特别是在治疗方面的用途。更具体地说，它涉及至少具有两个芳香环的衍生化合物，它们的制备和用途，特别是在人类或动物健康领域。这些化合物对存在于中枢和外周神经系统中的神经肽Y（NPY）的生物受体具有亲和力。本发明的化合物优选为NPY拮抗剂，更具体地说是NPY Y1亚型的拮抗剂，因此可用于治疗或预防涉及NPY的任何疾病。本发明还涉及含有所述化合物的药物组合物，其制备和用途，以及使用所述化合物的治疗方法。
• PHARMACEUTICAL COMPOUNDS AS INHIBITORS OF CELL PROLIFERATION AND THE USE THEREOF
  申请人：ANDERSON MARK B.

  公开号：US20100068197A1

  公开（公告）日：2010-03-18

  Disclosed are compounds of Formula I effective as cytotoxic agents. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  揭示的是作为细胞毒性剂有效的I式化合物。本发明的化合物在治疗多种临床病况中是有用的，这些病况中发生异常细胞的不受控制的生长和扩散。

表征谱图