5-氨基-1(2H)-异喹啉酮 | 93117-08-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 异喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 5-氨基-1(2H)-异喹啉酮
• 中文别名: 5-氨基-2H-异喹啉-1-酮；1-羟基-5-氨基异喹啉
• 英文名称: 5-aminoisoquinolin-1(2H)-one
• 英文别名: 5-aminoisoquinolinone；5-AIQ；5-amino-1(2H)-isoquinolinone；5-amino-2H-isoquinolin-1-one
• CAS: 93117-08-9
• 化学式: C₉H₈N₂O
• mdl: MFCD06198896
• 分子量: 160.175
• InChiKey: SVASVGVAQIVSEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  249-250°C
• 密度：
  1.287
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  | 室温 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Amino-2h-isoquinolin-1-one
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-Amino-2h-isoquinolin-1-one
CAS number: 93117-08-9

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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: C9H8N2O
Molecular weight: 160.2

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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

制备方法与用途

5-AIQ（5-氨基异喹啉-1-酮）是一种水溶性PARP-1抑制剂，广泛用作各种药物中的重要功能基团。研究表明，5-AIQ能够有效减少肝脏缺血再灌注引起的组织损伤，适用于研究相关的治疗条件[1][2]。

反应信息

• 作为反应物：
  描述：

  5-氨基-1(2H)-异喹啉酮 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  发现新的选择性糖皮质激素受体激动剂

  摘要：

  我们报告了两个新的铅系列糖皮质激素受体激动剂的发展的发现。首先，四氢萘的发现导致了代谢稳定和离解的化合物。它们与糖皮质激素受体的结合模式可通过X射线结构阐明。对反应路径的仔细检查和副产物的分析显示，新的氨基醇系列也解决了糖皮质激素受体的问题，并在体外显示出强大的抗炎活性。

  DOI：

  10.1016/j.bmcl.2016.12.047
• 作为产物：
  描述：

  5-硝基-1(2H)-异喹啉酮 在 palladium-carbon silica gel 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以to give 5-amino-2H-isoquinolin-1-one (620 mg, 70%)的产率得到5-氨基-1(2H)-异喹啉酮
  参考文献：
  名称：

  PENTADIENAMIDE DERIVATIVES

  摘要：

  本发明提供了一种由以下公式（I）表示的五二烯酰胺衍生物：（其中，R1代表取代或未取代的芳基或取代或未取代的芳香杂环基；R2代表取代或未取代的芳基，取代或未取代的芳香杂环基，取代或未取代的杂环螺环基或类似物；R3代表氢原子或与R4及其相邻的氮原子结合形成取代或未取代的杂环基；R4代表取代或未取代的芳基，取代或未取代的芳香杂环基，取代或未取代的杂环螺环基或类似物，或与R3及其相邻的氮原子结合形成取代或未取代的杂环基；R5、R6和R7可以相同也可以不同，每个代表氢原子或甲基）或其药学上可接受的盐等。

  公开号：

  US20090203667A1

文献信息

• Design, synthesis and biological activity of novel molecules designed to target PARP and DNA
  作者：Elliot Goodfellow、Zhor Senhaji Mouhri、Christopher Williams、Bertrand J. Jean-Claude

  DOI：10.1016/j.bmcl.2016.09.054

  日期：2017.2

  or 2 deficient tumours, we designed a series of molecules containing a 1,2,3-triazene moiety tethered to a PARP targeting scaffold. A cell-based selectivity assay involving a BRCA2-deficient Chinese hamster cell line and its corresponding BRCA2 wild type transfectant, was used to predict the PARP targeting potential of the latter agents. The results showed that adding a DNA damaging function to the PARP

  为了增强BRCA1或2型缺乏肿瘤中聚（ADP-核糖）聚合酶（PARP）抑制剂的细胞毒性潜能，我们设计了一系列分子，这些分子包含与PARP靶向支架相连的1,2,3-三氮烯部分。基于细胞的选择性测定涉及BRCA2缺陷型中国仓鼠细胞系及其对应的BRCA2野生型转染子，用于预测后一种药物的PARP靶向潜力。结果表明，向PARP抑制剂中添加DNA破坏功能有所降低，但并未消除BRCA2缺陷型细胞的选择性靶向作用。DNA损伤部分增强了BRCA2的效力细胞缺陷减少2–20倍。发现最具选择性的双重PARP-DNA靶向剂14b具有双重DNA和PARP靶向特性。
• N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems
  作者：Sandra Ferrer、Declan P. Naughton、Ifat Parveen、Michael D. Threadgill

  DOI：10.1039/b109776h

  日期：2002.1.23

  Regioselective methods were investigated to prepare N- and O-alkylated isoquinolin-1-ones efficiently. The predicted regioselective alkylation of the nitrogen with (hetero)benzyl halides was complemented using (hetero)benzylic Mitsunobu electrophiles to alkylate predominantly at the oxygen. A series of drug-delivery conjugates was prepared demonstrating control over the site of alkylation. The Mitsunobu reaction provides a new approach to 1-alkoxyisoquinolines that were unavailable via previous harsher synthetic methods.

  研究了区域选择性方法，以高效制备N-和O-烷基化的异喹啉-1-酮。通过使用（杂）苄基 Mitsunobu 亲电试剂，补充了氮的区域选择性烷基化，主要在氧处进行烷基化。制备了一系列药物输送偶联物，展示了烷基化位点的控制。Mitsunobu 反应为通过先前较为苛刻的合成方法无法获得的1-烷氧基异喹啉提供了一种新途径。
• Rearranged pentanols, a process for their production and their use as anti-inflammatory agents
  申请人：Rehwinkel Hartmut

  公开号：US20050131226A1

  公开（公告）日：2005-06-16

  The invention relates to the compounds of formula I, a process for their production and their use as anti-inflammatory agents.

  这项发明涉及到式I的化合物，以及它们的生产过程和作为抗炎药物的用途。
• [DE] UMGELAGERTE PENTANOLE, EIN VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS ENTZÜNDUNGSHEMMER<br/>[EN] REARRANGED PENTANOLS, A METHOD FOR THE PRODUCTION THEREOF, AND THEIR USE AS ANTIPHLOGISTICS<br/>[FR] PENTANOLS REARRANGES, UN PROCEDE POUR LEUR PRODUCTION ET LEUR UTILISATION EN TANT QU'ANTI-INFLAMMATOIRES
  申请人：SCHERING AG

  公开号：WO2005035518A1

  公开（公告）日：2005-04-21

  Die Erfindung betrifft Verbindungen der Formel (I), ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer.

  这项发明涉及公式（I）的化合物，其制备方法以及它们作为抗炎药物的用途。
• [DE] TETRAHYDRONAPHTHALINDERIVATE, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS ENTZÜNDUNGSHEMMER<br/>[EN] 1-AMINO-2-OXY-SUBSTITUTED TETRAHYDRONAPHTALENE DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF, AND THEIR USE AS ANTIPHLOGISTICS<br/>[FR] DERIVES DE TETRAHYDRONAPHTALENE A SUBSTITUTION 1-AMINO-2-OXY, PROCEDES POUR LEUR PRODUCTION ET LEUR UTILISATION EN TANT QU'ANTI-INFLAMMATOIRES
  申请人：SCHERING AG

  公开号：WO2005034939A1

  公开（公告）日：2005-04-21

  Die Erfindung betrifft mehrfach substituierte Tetrahydronaphthalinderivate der Formel (I), Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer.

  这项发明涉及公式（I）的多取代四氢萘衍生物，其制备方法以及它们作为抗炎药物的用途。