5-羟基-1H-咪唑-4-甲酰胺 | 56973-26-3

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 5-羟基-1H-咪唑-4-甲酰胺
• 中文别名: 5-羟基-4-甲酰氨基-1H-咪唑
• 英文名称: 5-hydroxy-1H-imidazole-4-carboxamide
• 英文别名: 4(5)-hydroxy-5(4)-imidazolecarboxamide；mizoribine nucleobase；5-oxo-4,5-dihydro-1(3)H-imidazole-4-carboxylic acid amide；4-carbamoyl-5-hydroxyimidazole；4-Carbamoyl-5-hydroxyimidazol；5-Hydroxyimidazolo-4-carboxamid；4-hydroxy-1H-imidazole-5-carboxamide
• CAS: 56973-26-3
• 化学式: C₄H₅N₃O₂
• mdl: MFCD06797616
• 分子量: 127.103
• InChiKey: UEWSIIBPZOBMBL-UHFFFAOYSA-N

物化性质

• 熔点：
  260°C
• 沸点：
  575.0±35.0 °C(Predicted)
• 密度：
  1.627
• 溶解度：
  DMSO（少许）、水（少许）

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：
  92
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Hydroxy-1h-imidazole-4-carboxamide
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: 5-Hydroxy-1h-imidazole-4-carboxamide
CAS number: 56973-26-3

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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: C4H5N3O2
Molecular weight: 127.1

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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

生物活性方面，bredinin aglycone（5-羟基咪唑-4-甲酰胺）是一种嘌呤核苷酸类似物，可用于评估嘌呤核苷酸类似物催化剂的效率。

反应信息

• 作为反应物：
  描述：

  5-羟基-1H-咪唑-4-甲酰胺 在 硫酸 、 水 作用下， 反应 0.5h， 以1.8 g的产率得到5-hydroxy-1H-imidazole-4-carboxamide sulfate
  参考文献：
  名称：

  SULFATE OF 5-HYDROXY-1H-IMIDAZOLE-4-CARBOXAMIDE

  摘要：

  5-羟基-1H-咪唑-4-甲酰胺硫酸盐具有抑制蓝色染色、高纯度、低吸湿性和优异的储存稳定性等特性，因此可用作药物的活性成分。

  公开号：

  US20150266826A1
• 作为产物：
  描述：

  5-(3,3-dimethyl-1-triazeno)imidazone-4-carboxamide 以 水 为溶剂， 生成 5-羟基-1H-咪唑-4-甲酰胺
  参考文献：
  名称：

  A new light on the photo-decomposition of the antitumour drug DTIC

  摘要：

  DOI：

  10.1111/j.2042-7158.1981.tb13944.x

文献信息

• 4-Carbamoylimidazolium-5-olate derivatives
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04464531A1

  公开（公告）日：1984-08-07

  There are provided compounds of the formula: ##STR1## wherein either R.sub.1 or R.sub.2 is a hydrogen atom, a hydroxy group, an acyloxy group, a phthalimido group or an acetamido group and the other is a hydrogen atom; either R.sub.3 or R.sub.4 is a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R.sub.5 or R.sub.6 is a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R.sub.7 or R.sub.8 is a hydrogen atom, a methyl group, a hydroxymethyl group, an acyloxymethyl group, an alkoxycarbonyl group, a group of the formula: ##STR2## (wherein X.sub.1 and X.sub.2 are a hydrogen atom or a lower alkyl group), or a carboxyl group and the other is a hydrogen atom; either R.sub.11 or R.sub.12 is a hydrogen atom, a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R.sub.13 or R.sub.14 is a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R.sub.15 or R.sub.16 is a methyl group, a hydroxymethyl group or an acyloxymethyl group and the other is a hydrogen atom; and a process for producing them. These compounds are useful as antitumor agents.

  提供的化合物具有以下结构：##STR1## 其中R.sub.1或R.sub.2是氢原子、羟基、酰氧基、邻苯二甲酰亚胺基团或乙酰氨基团之一，另一个是氢原子；R.sub.3或R.sub.4是羟基或酰氧基之一，另一个是氢原子；R.sub.5或R.sub.6是羟基或酰氧基之一，另一个是氢原子；R.sub.7或R.sub.8是氢原子、甲基、羟甲基、酰氧甲基、烷氧羰基、##STR2##（其中X.sub.1和X.sub.2是氢原子或较低的烷基基团）或羧基之一，另一个是氢原子；R.sub.11或R.sub.12是氢原子、羟基或酰氧基之一，另一个是氢原子；R.sub.13或R.sub.14是羟基或酰氧基之一，另一个是氢原子；R.sub.15或R.sub.16是甲基、羟甲基或酰氧甲基之一，另一个是氢原子；以及生产这些化合物的方法。这些化合物可用作抗肿瘤剂。
• 5-Carbamoyl imidazoles
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04260774A1

  公开（公告）日：1981-04-07

  There are provided compounds of the formula: ##STR1## wherein R is an adamantyl group, or a phenyl group unsubstituted or substituted with a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halogen atom, a nitro group, a cyano group, a methylenedioxy group or an acetamido group, useful as anti-transplanted-tumor agents and immunosuppressants.

  提供了以下式的化合物：##STR1## 其中 R 是一个金刚烷基团，或者是一个未取代或取代有较低烷基团、较低烷氧基团、较低烷硫基团、卤原子、硝基团、氰基团、亚甲二氧基基团或乙酰胺基团的苯基团，可用作抗移植肿瘤药物和免疫抑制剂。
• Studies on imidazole derivatives and related compounds. I. Synthesis of novel antineoplastic derivatives of 4-carbamoylimidazolium-5-olate
  作者：Y. Tarumi、Y. Takebayashi、K. Moriguchi、T. Atsumi、T. Fukumaru、H. Yamamoto

  DOI：10.1002/jhet.5570170715

  日期：1980.11

  diazomethane gave the N-3 methyl derivative (6) and a mixture of the N-3, O-dimethyl derivative (9), the N-1, N-3-dimethyl derivative (10) and the O-methyl derivative (11), respectively. 5-Carbamoyl-1-methylimidazolium-4-olate (7) and its 4-carbamoyl isomer (16) were prepared from 2-aminopropanediamides 8 and 15, respectively. Treatment of the imidazolium compound (10) with aqueous potassium hydroxide

  用各种酰基氯酰化4-氨基甲酰基咪唑鎓5-油酸酯（2），产生4（5）-氨基甲酰基-1 H-咪唑-5-（4）酰基羧酸酯（3a-j）。用氢氧化钠处理酯3a，c，得到酰亚胺4a，c。3a和2用重氮甲烷甲基化得到N -3甲基衍生物（6）和N -3，O-二甲基衍生物（9），N -1，N -3-二甲基衍生物（10）和N -3的混合物邻甲基衍生物（11）， 分别。由2-氨基丙烷二酰胺8和15分别制备5-氨基甲酸酯基-1-甲基咪唑-4-油酸酯（7）及其4-氨基甲酰基异构体（16）。用氢氧化钾水溶液处理咪唑鎓化合物（10），得到再循环的产物1-甲基-5-甲基氨基甲酰咪唑鎓4-油酸酯（18）。除16之外的甲基衍生物6、7和9证明对小鼠的Lewis肺癌或肉瘤180完全缺乏抗肿瘤活性。
• Antitumor and immunosuppressive 4-carbamoyl imidazolium-5-olate
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04317825A1

  公开（公告）日：1982-03-02

  There are provided compounds of the formula: ##STR1## wherein R is a heteroaroyl group containing a nitrogen, sulfur or oxygen atom which may be substituted with a lower alkyl group, an aralkyl group, an acyl group or a halogen atom; or a cycloalkanoyl group which may be substituted with a lower alkyl group, a lower alkenyl group, a halogen atom, a halogeno-lower alkenyl group, a phenyl group, a halogenophenyl group, a lower alkoxyphenyl group, a lower alkylphenyl group, a formyl group, a hydroxy group, an amino group, a carboxyl group, an aminomethyl group or an oxo group, its non toxic salt and a process for producing them. These compounds are useful as antitumor agents and immunosuppressants.

  提供了以下化合物的结构式：##STR1## 其中R是含有氮、硫或氧原子的杂芳基团，可以被较低的烷基团、芳基烷基团、酰基或卤素原子取代；或者是可以被较低的烷基团、较低的烯基团、卤素原子、卤素较低的烯基团、苯基、卤苯基、较低的烷氧基苯基、较低的烷基苯基、甲酰基、羟基、氨基、羧基、氨甲基基团或氧代基团取代的环烷酰基团，其无毒盐及其制备方法。这些化合物可用作抗肿瘤剂和免疫抑制剂。
• Antitumor and immunosuppressive 4-carbamoylimidazolium-5-olate
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04410696A1

  公开（公告）日：1983-10-18

  There are provided compounds of the formula: ##STR1## wherein R is a mono-substituted benzoyl group wherein the substituent is a phenyl group, an alkanoyl group, a formyl group, a halogeno-alkyl group, an aralkyloxy group, a phenoxy group, an alkoxycarbonyl group, an aralkyloxycarbonyl group, an alkanoyloxy group, a benzoyl group, a carboxyl group, a hydroxy group, a group of the formula: ##STR2## (wherein X.sub.1 and X.sub.2 are a hydrogen atom or a lower alkyl group), an aralkyloxycarbonylamino group, a lower alkoxycarbonylamino group, a carboxyamino group or a carbamoyl group; a cinnamoyl group which may be substituted at the .alpha. position or the phenyl ring with an alkyl group, an alkoxy group, an aryl group, a nitro group, a methylenedioxy group, a formyl group, a halogeno-alkyl group, a halogen atom, a hydroxy group, a carboxyl group, an amino group or a cyano group; or a benzoyl group substituted with from two to five of the same or different substituents selected from the group consisting of alkyl groups, alkoxy groups, aralkyloxy groups, nitro group, halogen atoms, hydroxy group, alkanoyloxy groups, formyl group, carboxyl group, alkylthio groups, alkylsulfonyl groups, groups of the formula: ##STR3## (wherein X.sub.1 and X.sub.2 are a hydrogen atom or a lower alkyl group), sulfo group and sulfamoyl group; or its non-toxic salt, and a process for producing them. The compounds are useful as antitumor agents and immunosuppressants.

  提供的化合物具有以下结构式：其中R是一个单取代苯甲酰基团，其中取代基是苯基、烷酰基、甲酰基、卤代烷基、芳基氧基、苯氧基、烷氧羰基、芳基氧羰基、烷酰氧基、苯甲酰基、羧基、羟基、下述结构式的基团：（其中X₁和X₂是氢原子或低碳基）、芳基氧羰胺基团、低碳氧羰胺基团、羧胺基团或氨基甲酰基团；可在α位或苯环上用烷基、烷氧基、芳基、硝基、亚甲二氧基、甲酰基、卤代烷基、卤原子、羟基、羧基、氨基或氰基取代的肉桂酰基；或用从两个到五个相同或不同的取代基选自烷基、烷氧基、芳基氧基、硝基、卤原子、羟基、烷酰氧基、甲酰基、羧基、烷硫基、烷磺基、下述结构式的基团：（其中X₁和X₂是氢原子或低碳基）、磺基和磺胺基取代的苯甲酰基；或其无毒盐，以及生产它们的方法。这些化合物可用作抗肿瘤剂和免疫抑制剂。