1-甲基-6-氨基-1H-吲唑 | 74728-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 1-甲基-6-氨基-1H-吲唑
• 中文别名: 6-氨基-1-甲基-1H-吲唑
• 英文名称: 1-methyl-1H-indazol-6-ylamine
• 英文别名: 1-methyl-1H-indazol-6-amine；1-methyl-6-aminoindazole；6-amino-1-methyl-indazole；1-methyl-6-amino-1H-indazole；6-amino-1-methyl-1H-indazole；1-methylindazol-6-amine
• CAS: 74728-65-7
• 化学式: C₈H₉N₃
• 分子量: 147.18
• InChiKey: YTKNUPJYGSOVLV-UHFFFAOYSA-N

物化性质

• 熔点：
  172-173
• 沸点：
  321.6±15.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 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：
  存储温度应保持在2-8°C，并避免光照。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Methyl-1h-indazol-6-ylamine
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: 1-Methyl-1h-indazol-6-ylamine
CAS number: 74728-65-7

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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: C8H9N3
Molecular weight: 147.2

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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：

  1-甲基-6-氨基-1H-吲唑 在 硫酸 、 水 、 sodium nitrite 作用下， 反应 4.0h， 以300 mg的产率得到1-甲基-6-羟基-1H吲唑
  参考文献：
  名称：

  [EN] PRMT5 INHIBITORS CONTAINING A DIHYDRO- OR TETRAHYDROISOQUINOLINE AND USES THEREOF
  [FR] INHIBITEURS DE LA PRMT5 CONTENANT UNE DIHYDRO- OU TÉTRAHYDRO-ISOQUINOLÉINE ET LEURS UTILISATIONS

  摘要：

  本文描述了式（A）的化合物，其药学上可接受的盐以及药物组合物。本发明的化合物对抑制PRMT5活性是有用的。还描述了利用这些化合物治疗PRMT5介导的疾病的方法。

  公开号：

  WO2014100730A1
• 作为产物：
  描述：

  6-硝基吲唑 在 铁粉 、 sodium hydride 、 氯化铵 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 1-甲基-6-氨基-1H-吲唑
  参考文献：
  名称：

  靶向PI3K/AKT/mTOR通路的1H-吲唑类衍生物的合成、抗肿瘤作用及分子机制

  摘要：

  PI3K/AKT/mTOR信号通路是肿瘤细胞中最常见的异常激活通路之一，与肿瘤细胞的生长、增殖、迁移、侵袭和肿瘤血管生成等多种功能相关。在这里，合成了一系列 3-氨基-1H-吲唑衍生物，并评估了它们对 HT-29、MCF-7、A-549、HepG2 和 HGC-27 细胞的抗增殖活性。其中，W24对四种癌细胞表现出广谱抗增殖活性，IC 50值为0.43–3.88 μM。机制研究表明，W24通过影响 DNA 合成抑制增殖，诱导 G 2/M通过调控Cyclin B1、BAD和Bcl-xL导致细胞周期停滞和凋亡，同时诱导HGC-27细胞内ROS和线粒体膜电位的变化。此外，W24通过减少EMT通路相关蛋白和降低Snail、Slug和HIF-1α的mRNA表达水平来抑制HGC-27细胞的迁移和侵袭。此外，W24在体内表现出低组织毒性和良好的药代动力学特性。因此，3-氨基-1H-吲唑衍生物可能作为开发

  DOI：

  10.1016/j.bioorg.2023.106412

文献信息

• [EN] PYRROLOTRIAZINES AS ALK AND JAK2 INHIBITORS<br/>[FR] PYRROLOTRIAZINES EN TANT QU'INHIBITEURS D'ALK ET DE JAK2
  申请人：CEPHALON INC

  公开号：WO2010071885A1

  公开（公告）日：2010-06-24

  The present invention provides a compound of formula (I) or a salt form thereof, wherein Q1, Q2, Q3, and Q4 are as defined herein. The compound of formula (I) has ALK and/or JAK2 inhibitory activity, and may be used to treat proliferative disorders.

  本发明提供了一种式（I）的化合物或其盐形式，其中Q1、Q2、Q3和Q4如本文所定义。式（I）的化合物具有ALK和/或JAK2抑制活性，并可用于治疗增殖性疾病。
• PRMT5 INHIBITORS AND USES THEREOF
  申请人：Duncan Kenneth W.

  公开号：US20190083482A1

  公开（公告）日：2019-03-21

  Described herein are compounds of Formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

  本文描述了式（I）的化合物，其药学上可接受的盐以及药物组合物。本发明的化合物对抑制PRMT5活性是有用的。还描述了利用这些化合物治疗PRMT5介导的疾病的方法。
• [EN] PYRIMIDINE DERIVATIVES CAPABLE OF INHIBITING ONE OR MORE KINASES<br/>[FR] DÉRIVÉS DE PYRIMIDINE CAPABLES D'INHIBER UNE OU PLUSIEURS KINASES
  申请人：MEDICAL RES COUNCIL

  公开号：WO2009122180A1

  公开（公告）日：2009-10-08

  A first aspect of the invention relates to a compound of formula (I), or a pharmaceutically acceptable salt or ester thereof, formula (I): wherein: R1 is C3-8-cycloalkyl; X is O, NR7 or C3-6-heterocycloalkyl; R2 is aryl, heteroaryl, fused or unfused aryl-C3-6-heterocycloalkyl or fused or unfused heteroaryl-C3-6-heterocycIoalkyl, each of which is optionally substituted by one or more substitutents selected from aryl, heteroaryl, C1-6-alkyl, C3-7-cycloalkyl and a group A, wherein said C1-6-alkyl group is optionally substituted by one or more substituents selected from aryl, heteroaryl, R10 and a group A, said heteroaryl group is optionally substituted by one or more R10 groups; and wherein said C3-6-heterocycloalkyl group optionally contains one or more groups selected from oxygen, sulfur, nitrogen and CO; R3 is C1-6-alkyl optionally substituted by one or more substituents selected from aryl, heteroaryl, -NR4R5, -OR6, -NR7(CO)R6, -NR7(CO)NR4R5, -NR7SO2R6, -NR7COOR7, -CONR4R5, C3-6-heterocycloalkyl and formula (a, b, c): wherein R4-7 and A are as defined in the claims. Further aspects relate to the use of said compounds in the treatment of various therapeutic disorders, and more particularly as inhibitors of one or more kinases.

  本发明的第一个方面涉及式(I)的化合物，或其药学上可接受的盐或酯，式(I)如下：其中：R1为C3-8环烷基；X为O、NR7或C3-6杂环烷基；R2为芳基、杂芳基、融合或未融合的芳基-C3-6杂环烷基或融合或未融合的杂芳基-C3-6杂环烷基，每个基可选择地由来自芳基、杂芳基、C1-6烷基、C3-7环烷基和A基的一个或多个取代基取代，其中所述C1-6烷基基可选择地由来自芳基、杂芳基、R10和A基的一个或多个取代基取代，所述杂芳基可选择地由一个或多个R10基取代；以及所述C3-6杂环烷基基可选择地包含一个或多个来自氧、硫、氮和CO的基；R3为C1-6烷基，可选择地由一个或多个来自芳基、杂芳基、-NR4R5、-OR6、-NR7(CO)R6、-NR7(CO)NR4R5、-NR7SO2R6、-NR7COOR7、-CONR4R5、C3-6杂环烷基和式(a, b, c)的取代基取代；其中R4-7和A如权利要求中所定义。进一步方面涉及所述化合物在治疗各种治疗性疾病中的使用，特别是作为一个或多个激酶的抑制剂。
• TANK-BINDING KINASE INHIBITOR COMPOUNDS
  申请人：Gilead Sciences, Inc.

  公开号：US20160096827A1

  公开（公告）日：2016-04-07

  Compounds having the following formula (I) and methods of their use and preparation are disclosed:

  具有以下化学式（I）的化合物以及它们的使用和制备方法已被披露：
• Ligand-Promoted <i>Meta</i>-C–H Arylation of Anilines, Phenols, and Heterocycles
  作者：Peng Wang、Marcus E. Farmer、Xing Huo、Pankaj Jain、Peng-Xiang Shen、Mette Ishoey、James E. Bradner、Steven R. Wisniewski、Martin D. Eastgate、Jin-Quan Yu

  DOI：10.1021/jacs.6b04966

  日期：2016.7.27

  Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic

  在这里，我们报告了一种通用的 3-乙酰氨基-2-羟基吡啶类配体的开发，这些配体使用降冰片烯作为瞬态介质促进苯胺、杂环芳香胺、苯酚和 2-苄基杂环的间位 CH 芳基化。提供了 120 多个例子，证明了这种配体支架能够实现广泛的底物和偶联伙伴范围。使用该配体还首次实现了以杂环芳基碘化物作为偶联伙伴的间位 CH 芳基化。通过允许来那度胺衍生物的间位 CH 芳基化，展示了这种药物发现转化的效用。还展示了该反应的无银方案的第一步。