6-羟基-3-哒嗪甲酸 | 37972-69-3

• 物质功能分类: 有机原料 - 杂环化合物
• 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-羟基-3-哒嗪甲酸
• 中文别名: 6-氧代-1,6-二氢吡嗪-3-羧酸单水合物；6-羟基哒嗪-3-羧酸；6-氧代-1,6-二氢哒嗪-3-羧酸
• 英文名称: 6-oxo-1,6-dihydropyridazine-3-carboxylic acid
• 英文别名: 6-oxo-1H-pyridazine-3-carboxylic acid；6-Oxo-1,6-dihydro-pyridazin-carbonsaeure-(3)；6-hydroxypyridazine-3-carboxylic acid
• CAS: 37972-69-3
• 化学式: C₅H₄N₂O₃
• mdl: MFCD00052805
• 分子量: 140.098
• InChiKey: GIFSROMQVPUQFK-UHFFFAOYSA-N

物化性质

• 熔点：
  246 °C
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 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：
  78.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Hydroxypyridazine-3-carboxylic acid
Synonyms: 6-Oxo-1,6-dihydro-pyridazine-3-carboxylic acid

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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-Hydroxypyridazine-3-carboxylic acid
CAS number: 37972-69-3

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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: C5H4N2O3
Molecular weight: 140.1

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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

制备方法与用途

应用

6-氧代-1,6-二氢哒嗪-3-羧酸是一种有机中间体，可通过α-酮戊二酸先关环得到1,4,5,6-四氢-6-氧哒嗪-3-羧酸，再与溴反应制备而成。

制备

6-氧代-1,6-二氢哒嗪-3-羧酸：将2.50克(17.59毫米摩尔)的6-氧代-1,4,5,6-四氢哒嗪-3-羧酸溶解于44毫升甲苯中，室温下加入450毫克(2.48毫米摩尔)Cu(OAc)₂、7.01克(66.14毫米摩尔)碳酸钠和4.4毫升吡啶。所得溶液在100℃搅拌16小时后，待反应完成，滤出不溶固体，减压浓缩滤液以获得乳白色固体的6-氧代-1,6-二氢哒嗪-3-羧酸(1.80克，产率73％)。MS：m/z＝177.0[M+H]+。

反应信息

• 作为反应物：
  描述：

  6-羟基-3-哒嗪甲酸 在 氯化亚砜 、 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 反应 18.0h， 生成 6-氯哒嗪-3-甲酸甲酯
  参考文献：
  名称：

  小分子TGFβR1抑制剂BMS-986260的可扩展合成方法的开发

  摘要：

  开发了可扩展的小分子TGFβR1抑制剂BMS-986260（1）的途径。这种替代方法避免了通过柱色谱法纯化中间体的问题，并提供了获取多千克量的关键中间体6的途径。对API的其他片段（TosMIC 10）的合成方法的安全性进行了严格评估，并成功证明了其大规模合成的可靠过程。

  DOI：

  10.1021/acs.oprd.0c00232
• 作为产物：
  描述：

  alpha-酮戊二酸 在 溴 、 溶剂黄146 、 sodium hydroxide 、 硫酸肼 作用下， 以 水 为溶剂， 生成 6-羟基-3-哒嗪甲酸
  参考文献：
  名称：

  开发哒嗪-3-羧酰胺作为CB2激动剂：设计，合成，结构-活性关系和对接研究

  摘要：

  在这里，我们描述了通过支架跳跃和生物等排策略的组合，将一系列哒嗪-3-羧酰胺设计和合成为CB2选择性激动剂。通过钙动员测定法对化合物的潜在活性进行评估。在测试的衍生物中，这些化合物中超过一半的化合物表现出中等至有效的CB2激动剂活性。六种化合物的EC 50值低于35 nM，几种衍生物在CB2受体上的效力和选择性也大大高于CB1受体。具体而言，化合物26显示出最高的CB2激动剂活性（EC 50 ＝ 3.665±0.553nM）和对CB1的显着选择性（选择性指数＞ 2729）。此外，与GW842166X相比，一些代表性化合物的logPs被测量为显示出明显降低的值。此外，进行了对接仿真以解释该系列的交互模式。

  DOI：

  10.1016/j.ejmech.2017.05.060

文献信息

• Design, Synthesis, and Biological Evaluation of New 8-Heterocyclic Xanthine Derivatives as Highly Potent and Selective Human A_2B Adenosine Receptor Antagonists
  作者：Pier Giovanni Baraldi、Mojgan Aghazadeh Tabrizi、Delia Preti、Andrea Bovero、Romeo Romagnoli、Francesca Fruttarolo、Naser Abdel Zaid、Allan R. Moorman、Katia Varani、Stefania Gessi、Stefania Merighi、Pier Andrea Borea

  DOI：10.1021/jm0309654

  日期：2004.3.1

  in radioligand binding assays at human (h) A(1), A(2A), A(2B), and A(3) ARs. We introduced several heterocycles, such as pyrazole, isoxazole, pyridine, and pyridazine, at the 8-position of the xanthine nucleus and we have also investigated different spacers (substituted acetamide, oxyacetamide, and urea moieties) on the heterocycle introduced. Various groups at the 3- and 4-positions of phenylacetamide

  在这里，我们报告8杂环取代的黄嘌呤作为有效和选择性A（2B）腺苷受体拮抗剂的合成。探索了黄嘌呤与重组人A（2B）腺苷受体（ARs）结合在HEK-293细胞（HEK-A（2B））和其他AR亚型中的结构活性关系（SAR）。合成的化合物在纳摩尔浓度范围内显示出A（2B）腺苷受体亲和力，并且在人类（h）A（1），A（2A），A（2B）和A（3）的放射性配体结合测定中评估了良好的选择性水平AR。我们在黄嘌呤核的8位引入了几个杂环，例如吡唑，异恶唑，吡啶和哒嗪，我们还研究了所引入杂环上的不同间隔基（取代的乙酰胺，氧乙酰胺和脲部分）。研究了苯基乙酰胺部分的3位和4位上的各种基团。这项研究使我们能够确定衍生物2-（3,4-二甲氧基苯基）-N- [5-（2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin- 8-基）-1-甲基-1H-吡唑-3-基]乙酰胺（29
• TBK/IKK INHIBITOR COMPOUNDS AND USES THEREOF
  申请人：Merck Patent GmbH

  公开号：US20160376283A1

  公开（公告）日：2016-12-29

  The present invention relates to compounds of Formula I and pharmaceutically acceptable compositions thereof, useful as TBK/IKKε inhibitors.

  本发明涉及式I化合物及其药用可接受的组合物，用作TBK/IKKε抑制剂。
• 8-Heteroaryl xanthine adenosine A2B receptor antagonists
  申请人：——

  公开号：US20030207879A1

  公开（公告）日：2003-11-06

  The present invention relates generally to compounds of formula (IA): (IA) 1 the preparation thereof, pharmaceutical formulations thereof, and their use in medicine as potent or selective A 2B adenosine receptor antagonists and their uses for treating asthma, autoimmune diseases and retinal vascular diseases.

  本发明总体上涉及公式（IA）的化合物：(IA)1，其制备方法、药物制剂及其在医学中的应用，作为强效或选择性的A2B腺苷受体拮抗剂，以及用于治疗哮喘、自身免疫疾病和视网膜血管疾病的用途。
• [EN] INHIBITORS OF WDR5 PROTEIN-PROTEIN BINDING<br/>[FR] INHIBITEURS DE LA LIAISON ENTRE LA PROTÉINE WDR5 ET SES PARTENAIRES DE LIAISON
  申请人：ONTARIO INST FOR CANCER RES (OICR)

  公开号：WO2017147701A1

  公开（公告）日：2017-09-08

  The present application is directed to compounds of Formula I: (I) compositions comprising these compounds and their uses, for example as medicaments for the treatment of diseases, disorders or conditions mediated or treatable by inhibition of binding between WDR5 protein and its binding partners.

  本申请涉及到Formula I的化合物：(I) 包含这些化合物的组合物及其用途，例如作为治疗由于抑制WDR5蛋白与其结合伙伴之间结合而介导或可治疗的疾病、紊乱或状况的药物。
• Synthesis, tautomeric forms, specific intermolecular interactions, and lipophilicity of methylated 6-hydroxypyridazine-3-carboxylic acid and its 4,5-dihydro analogs
  作者：Anna Katrusiak、Paweł Piechowiak、Andrzej Katrusiak

  DOI：10.1016/j.molstruc.2011.05.016

  日期：2011.7

  derivatives. Carboxylic acid 2 preferably crystallizes as a hydrate, built of carboxylate anions and hydronium cations 2− H3O+, hydrogen bonded into catemeric patterns involving both ions. In methyl 4,5-dihydro-6-oxopyridazine-3-carboxylate (4A) the molecules are NH⋯O hydrogen bonded into chains. In both structures 2− H3O+ and 4A, there are relatively strong CH⋯O hydrogen bonds, arranging the molecules

  摘要 已经研究了一系列甲基化 4,5-二氢-6-羟基哒嗪-3-羧酸和 6-羟基哒嗪-3-羧酸（1 和 2）的甲基化对分子间相互作用和亲脂性的影响。在溶液中，它们以内酰胺和内酰胺互变异构体的平衡状态存在，类似物 1 和 2 的相反偏好会影响其甲基化衍生物的合成。羧酸 2 优选以水合物的形式结晶，由羧酸根阴离子和水合氢阳离子 2- H3O+ 构成，氢键结合成涉及这两种离子的分子式模式。在 4,5-dihydro-6-oxopyridazine-3-carboxylate (4A) 中，分子由 NH⋯O 氢键连接成链。在 2− H3O+ 和 4A 两种结构中，都有相对较强的 CH⋯O 氢键，将分子排列成片状。