2-甲氧基-5-氨基嘧啶 | 56621-89-7

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 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: 2-甲氧基-5-氨基嘧啶
• 英文名称: 2-methoxypyrimidin-5-amine
• 英文别名: 5-amino-2-methoxypyrimidine；2-methoxy-5-aminopyrimidine；5-Amino-2-methoxy-pyrimidin
• CAS: 56621-89-7
• 化学式: C₅H₇N₃O
• 分子量: 125.13
• InChiKey: HKHRENFWPKWVML-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C(Solv: benzene (71-43-2))
• 沸点：
  294.4±32.0 °C(Predicted)
• 密度：
  1.224±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：
  0.2
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methoxypyrimidin-5-amine
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: 2-Methoxypyrimidin-5-amine
CAS number: 56621-89-7

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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: C5H7N3O
Molecular weight: 125.1

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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

反应信息

• 作为反应物：
  描述：

  2-甲氧基-5-氨基嘧啶 在 氧气 、 Streptomyces chattanoogensis AzoC N-oxygenase 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  非血红素二铁N-加氧酶AzoC的定向进化以提高其对氮杂环底物的催化效率

  摘要：

  已知具有有趣化学键 [-N=N+(-O-)-] 的偶氮氧基化合物在许多行业中具有广泛的应用。我们之前的工作表明，在偶氮霉素生物合成中，非血红素二铁 N-加氧酶 AzoC 催化氨基氧化成亚硝基类似物，形成偶氮键。然而，除已报道的吡啶类生物碱偶氮氧基化合物外，目前大部分氮杂环的偶氮键尚未被生物合成，AzoC的底物范围仅限于对氨基苯类化合物。因此，利用AzoC实现偶氮氮杂环化合物的生物合成具有非常重要的意义。在这项工作中，我们进一步研究了AzoC对包括5-氨基嘧啶和5-氨基吡啶化合物在内的氮杂环底物的催化潜力，以通过定向进化形成新的偶氮氧基化合物。我们通过分子工程构建了双突变体 L101I/Q104R，提高了对 2-甲氧基嘧啶-5-胺的催化效率。这些突变也被证明有利于 5-氨基嘧啶-2-羧酸甲酯的 N-氧化。结构分析表明，相对较短的底物与二铁中心和活性中心的氨基酸残基之间的距离可能是L101I/

  DOI：

  10.3390/molecules27030868
• 作为产物：
  描述：

  2-甲氧基-5-硝基嘧啶 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以97%的产率得到2-甲氧基-5-氨基嘧啶
  参考文献：
  名称：

  效力和药代动力学的并行优化导致吡咯甲酰胺 ERK5 激酶结构域抑制剂的发现

  摘要：

  非经典细胞外信号相关激酶 5 (ERK5) 丝裂原激活蛋白激酶途径与细胞增殖、迁移、存活和血管生成的增加有关；因此，ERK5抑制可能是一种有吸引力的癌症治疗方法。然而，选择性 ERK5 抑制剂的开发一直充满挑战。之前，我们描述了吡咯甲酰胺高通量筛选靶点的开发，使其成为 ERK5 激酶活性的选择性亚微摩尔抑制剂。提高 ERK5 效力对于鉴定用于靶标验证研究的 ERK5 抑制剂工具是必要的。在此，我们描述了该系列的优化，以鉴定包含基本中心的 ERK5 纳摩尔吡咯甲酰胺抑制剂，但其口服生物利用度较差。效力和体外药代动力学参数的并行优化导致鉴定出具有 ERK5 抑制和口服暴露最佳平衡的非碱性吡唑类似物。

  DOI：

  10.1021/acs.jmedchem.1c01756

文献信息

• PYRIMIDINYL AND 1,3,5-TRIAZINYL BENZIMIDAZOLES AND THEIR USE IN CANCER THERAPY
  申请人：Rewcastle Gordon William

  公开号：US20110009405A1

  公开（公告）日：2011-01-13

  Provided herein are pyrimidinyl and 1,3,5-triazinyl benzimidazoles of Formula I, and their pharmaceutical compositions, preparation, and use as agents or drugs for cancer therapy, either alone or in combination with radiation and/or other anticancer drugs.

  本文提供了式I的嘧啶基和1,3,5-三嗪基苯并咪唑化合物，以及它们的药物组合物、制备方法，以及作为抗癌治疗药物或药剂的用途，可以单独使用，也可以与放疗和/或其他抗癌药物联合使用。
• IDO INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160289171A1

  公开（公告）日：2016-10-06

  There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.

  已披露的化合物可调节或抑制吲哌酮胺2,3-二氧化酶（IDO）的酶活性，含有该化合物的药物组合物以及利用本发明的化合物治疗增殖性疾病，如癌症、病毒感染和/或炎症性疾病的方法。
• [EN] BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS<br/>[FR] COMPOSÉS BICYCLIQUES SUBSTITUÉS PAR HÉTÉROARYLE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018013774A1

  公开（公告）日：2018-01-18

  Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

  公开了公式(I)至(VIII)的化合物：(I) (II) (III) (IV) (V) (VI) (VII) (VIII)；或其立体异构体、互变异构体、药物可接受的盐、溶剂化物或前药，其中R3是与0至3个R3a取代的双环杂芳基团；且R1、R2、R3a、R4和n在此定义。还公开了使用这些化合物作为PAR4抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物用于抑制或预防血小板聚集，用于治疗血栓栓塞障碍或作为血栓栓塞障碍的初级预防。
• [EN] TRICYCLIC HETEROARYL-SUBSTITUTED QUINOLINE AND AZAQUINOLINE COMPOUNDS AS PAR4 INHIBITORS<br/>[FR] COMPOSÉS TRICYCLIQUES DE QUINOLÉINE ET D'AZAQUINOLINE À SUBSTITUTION HÉTÉROARYLE INHIBITEURS DE PAR4
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018013776A1

  公开（公告）日：2018-01-18

  Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII) or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a tricyclic heteroaryl group substituted with R3a and zero to 2 R3b; and R1, R2, R3a, R3b, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

  揭示了化合物的结构式（I）至（VIII）：（I）（II）（III）（IV）（V）（VI）（VII）（VIII）或其立体异构体、互变异构体、药学上可接受的盐、溶剂合物或前药，其中R3是一个三环杂芳基，其上取代有R3a和零至2个R3b；R1、R2、R3a、R3b、R4和n在此有定义。还揭示了将这些化合物用作PAR4抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物在抑制或预防血小板聚集方面很有用，并且可用于治疗血栓栓塞性疾病或血栓栓塞性疾病的初级预防。
• Discovery and Preclinical Evaluation of BMS-986242, a Potent, Selective Inhibitor of Indoleamine-2,3-dioxygenase 1
  作者：Emily C. Cherney、Liping Zhang、Susheel Nara、Xiao Zhu、Johnni Gullo-Brown、Derrick Maley、Tai-An Lin、John T. Hunt、Christine Huang、Zheng Yang、Celia Darienzo、Lorell Discenza、Asoka Ranasinghe、Mary Grubb、Theresa Ziemba、Sarah C. Traeger、Xin Li、Kathy Johnston、Lisa Kopcho、Mark Fereshteh、Kimberly Foster、Kevin Stefanski、Joseph Fargnoli、Jesse Swanson、Jennifer Brown、Diane Delpy、Steven P. Seitz、Robert Borzilleri、Gregory Vite、Aaron Balog

  DOI：10.1021/acsmedchemlett.0c00668

  日期：2021.2.11

  Indoleamine 2,3-dioxygenase 1 (IDO1) is a heme-containing dioxygenase enzyme implicated in cancer immune response. This account details the discovery of BMS-986242, a novel IDO1 inhibitor designed for the treatment of a variety of cancers including metastatic melanoma and renal cell carcinoma. Given the substantial interest around this target for cancer immunotherapy, we sought to identify a structurally

  吲哚胺 2,3-双加氧酶 1 (IDO1) 是一种含血红素的双加氧酶，与癌症免疫反应有关。该帐户详细介绍了 BMS-986242 的发现，这是一种新型 IDO1 抑制剂，旨在治疗多种癌症，包括转移性黑色素瘤和肾细胞癌。鉴于围绕这一癌症免疫治疗靶点的浓厚兴趣，我们试图确定一种结构差异化的临床候选药物，其在小鼠异种移植模型中的体外效力和体内药效学效果与 linrodostat (BMS-986205) 相当。根据其临床前概况，BMS-986242 被选为临床开发的候选者。