3-氨基呋咱-4-羧酸 | 78350-50-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 中文名称: 3-氨基呋咱-4-羧酸
• 中文别名: 4-氨基-1,2,5-恶二唑-3-羧酸；4-氨基-1,2,5-噁二唑-3-羧酸；4-氨基-1,2,5悪二唑-3-甲酸；4-氨基-1,2,5-噁二唑-3-甲酸
• 英文名称: 4-amino-1,2,5-oxadiazole-3-carboxylic acid
• 英文别名: 4-aminofurazan-3-carboxylic acid；3-aminofurazan-4-carboxylic acid；3-amino-4-carboxyfurazan；3-aminofurazancarboxylic acid
• CAS: 78350-50-2
• 化学式: C₃H₃N₃O₃
• mdl: MFCD00235172
• 分子量: 129.075
• InChiKey: YOXIXLVJYMCCIB-UHFFFAOYSA-N

物化性质

• 熔点：
  216-217 °C(Solv: water (7732-18-5))
• 沸点：
  385.4±52.0 °C(Predicted)
• 密度：
  1.756±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 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：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Amino-1,2,5-oxadiazole-3-carboxylic acid
Synonyms:

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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: 4-Amino-1,2,5-oxadiazole-3-carboxylic acid
CAS number: 78350-50-2

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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, refrigerated.
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: C3H3N3O3
Molecular weight: 129.1

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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

简介

呋喃环是一类重要的NO供体，可用于合成抑制白血病或其他癌细胞中核酸及蛋白质的药物。近年来还发现一些呋喃环化合物对艾滋病病毒有较好的抑制作用。在民用领域，呋喃类化合物常用作金属抛光剂、防腐剂、照相感光促进剂等。3-氨基呋咱-4-羧酸是合成呋喃、氧化呋喃、吡咯呋喃等化合物的重要中间体。

用途

3-氨基呋咱-4-羧酸是一种羧酸类有机物，它作为合成呋喃、氧化呋喃、吡咯呋喃等化合物的重要中间体具有重要意义。

合成方法

目前，3-氨基呋咱-4-羧酸的合成通常以氰基乙酸甲酯为原料，通过与盐酸羟胺反应来制备。

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  4-氨基-1,2,5-恶二唑-3-羧酸甲酯	3-amino-4-carbmethoxyfurazan	159013-94-2	C4H5N3O3	143.102
  4-氨基-1,2,5-噁二唑-3-甲酸乙酯	ethyl 4-amino-1,2,5-oxadiazole-3-carboxylate	17376-63-5	C5H7N3O3	157.129
  ——	4-amino-1,2,5-oxadiazole-3-methanol	1092310-34-3	C3H5N3O2	115.092
  4-(二氟氨基)-1,2,5-恶二唑-3-羧酸	4-(Difluoroamino)-1,2,5-oxadiazole-3-carboxylic acid	108284-66-8	C3HF2N3O3	165.056
  ——	4,4'-(methylenediimino)bis-1,2,5-oxadiazole-3-carboxylic acid	709623-88-1	C7H6N6O6	270.161

反应信息

• 作为反应物：
  描述：

  3-氨基呋咱-4-羧酸 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以50%的产率得到4-氨基-1,2,5-噁二唑-3-甲酸乙酯
  参考文献：
  名称：

  [EN] (4 -AMINO -1,2, 5-OXADIAZOL-4-YL) -HET?ROAROMATIC COMPOUNDS USEFUL AS PROTEIN KINASE INHIBITORS
  [FR] COMPOSES D'AMINOFURAZAN UTILES COMME INHIBITEURS DE PROTEINE-KINASES

  摘要：

  公开号：

  WO2005019190A3
• 作为产物：
  描述：

  氰乙酸乙酯 在 磷酸 、 盐酸羟胺 、 potassium hydroxide 、 sodium nitrite 作用下， 生成 3-氨基呋咱-4-羧酸
  参考文献：
  名称：

  基于呋喃山或4-硝基吡唑的非金属戊唑盐，可提高密度和稳定性

  摘要：

  在这项工作中，三种新的非金属五唑盐（6 - 8）的基础上或呋咱-4-硝基吡唑合成。将一些共面基团引入化合物中以改善晶体堆积的平面度。4-氨基1,2,5-恶二唑-3-碳酰肼酰胺五唑酸酯（6），5-（4-氨基1,2,5-恶二唑-3-基）-4 H -1,2,4-三唑-3,4-二胺五唑酸酯（7）和5,5'-（4-硝基-1 H-吡唑-3,5-二基）-双（4 H -1,2,4-三唑-3,4 -二胺）戊唑酸酯（8）均表现出比大多数其他报告的非金属戊唑盐（T发作）更稳定的π-π堆积和优异的热稳定性（110.5-116.4°C）。：80–110°C），并且化合物8具有迄今为止非金属戊唑盐的最高晶体密度（1.722 g·cm –3 / 173 K）。所有盐均已通过NMR（1 H和13 C）光谱，红外（IR），罗马（RA）和元素分析进行了全面表征。所有盐的分解温度均显示超过110°C，这是通过差示扫描量热法（D

  DOI：

  10.1021/acs.cgd.0c01574

文献信息

• IDO1 INHIBITOR AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：SHANDONG LUYE PHARMACEUTICAL CO., LTD.

  公开号：US20190169140A1

  公开（公告）日：2019-06-06

  A compound as an indoleamine-2,3-dioxygenase 1 (IDO1) inhibitor, and an application thereof in the field of IDO1-related diseases, and in particular a compound as shown in formula (I) and a pharmaceutically acceptable salts thereof.

  一种作为吲哌酮胺-2,3-二氧化酶1（IDO1）抑制剂的化合物，以及其在IDO1相关疾病领域中的应用，特别是如公式（I）所示的化合物及其药用可接受的盐。
• Modulators of indoleamine 2,3-dioxygenase and methods of using the same
  申请人：Combs P. Andrew

  公开号：US20060258719A1

  公开（公告）日：2006-11-16

  The present invention is directed to modulators of indoleamine 2,3-dioxygenase (IDO), as well as compositions and pharmaceutical methods thereof.

  本发明涉及色氨酸2,3-二氧化酶（IDO）的调节剂，以及其组合物和药用方法。
• Carbamic acid compounds comprising an amide linkage as hdac inhibitors
  申请人：——

  公开号：US20040092598A1

  公开（公告）日：2004-05-13

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the formula (1) wherein: A is an aryl group; Q1 is an aryl leader group having a backbone of at least 2 carbon atoms; J is an amide linkage selected from: —NR1C(═O)—and —C(═O)NR1—; R1 is an amido substituent; and, Q2 is an acid leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.

  这项发明涉及抑制HDAC活性的某些活性碳酸酰胺化合物，其化学式为（1），其中：A是芳基；Q1是至少有2个碳原子骨架的芳基前导基团；J是选择自以下的酰胺键：—NR1C(═O)—和—C(═O)NR1—；R1是酰胺取代基；Q2是酸前导基团；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这种化合物的药物组合物，以及在体外和体内使用这种化合物和组合物来抑制HDAC，例如，抑制增殖性疾病，如癌症和牛皮癣。
• Crystal structures of the “two” 4-aminofurazan-3-carboxylic acids
  作者：Rodney L. Willer、Robson F. Storey、Mark Frisch、Jeffery R. Deschamps

  DOI：10.1002/jhet.821

  日期：2012.1

  The crystal structures of the two compounds reported to be 4‐aminofurazan‐3‐carboxylic acid have been determined. The compound reported by Sheremetev et al. (J Heterocycl Chem 2005, 42, 519) is the actual 4‐aminofurazan‐3‐carboxylic acid. The compound reported by Meyer (Org Prep Proced Int 2004, 36, 361) is the interesting complex formed from a molecule of the acid and a molecule of the potassium salt

  已经确定了据报道为4-氨基呋喃-3-羧酸的两种化合物的晶体结构。Sheremetev等报道的化合物。（J Heterocycl Chem 2005，42，519）是实际的4-氨基呋喃赞纳3-羧酸。Meyer报告的化合物（Org Prep Proced Int 2004，36，361）是一种有趣的络合物，由酸的分子和酸的钾盐分子形成。J.杂环化​​学。（2012）。
• A Safer Synthesis of the Explosive Precursors 4-Aminofurazan-3-Carboxylic Acid and its Ethyl Ester Derivative
  作者：Christopher W. Miller、Eric C. Johnson、Rosario C. Sausa、Joshua A. Orlicki、Jesse J. Sabatini

  DOI：10.1021/acs.oprd.0c00068

  日期：2020.4.17

  A safe and efficient one-pot synthesis of 4-aminofurazan-3-carboxylic acid and its hydrogen chloride gas-free conversion to the ethyl ester derivative are described. Previous syntheses of these intermediates were plagued with mischaracterization issues, low yields, and/or dangerous exothermic profiles. The safe scale-up of these materials not only provides benefits to the energetic materials community

  描述了一种安全高效的4-氨基呋喃赞-3-羧酸的一锅法合成及其无氯化氢气体转化为乙酯衍生物的方法。这些中间体的先前合成方法受到误特征问题，低产率和/或危险的放热曲线的困扰。这些材料的安全放大不仅为高能材料领域提供了好处，而且对制药和农用化学工业也可能具有重要意义。