7,8-二氯异喹啉 | 61563-36-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 7,8-二氯异喹啉
• 英文名称: 7,8-dichloroisoquinoline
• CAS: 61563-36-8
• 化学式: C₉H₅Cl₂N
• mdl: MFCD09258638
• 分子量: 198.051
• InChiKey: MYYHZQIWSAUHJB-UHFFFAOYSA-N

物化性质

• 熔点：
  89-92
• 沸点：
  327.0±22.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933499090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 7,8-Dichloroisoquinoline
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: 7,8-Dichloroisoquinoline
CAS number: 61563-36-8

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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: C9H5Cl2N
Molecular weight: 198.0

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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, hydrogen chloride.

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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：

  7,8-二氯异喹啉 在 platinum(IV) oxide 氢气 、 乙酸酐 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 1.0h， 生成 2-acetyl-7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines

  摘要：

  In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2 greater than 6,7,8-Cl3 greater than 7-Cl approximately 5,6,7,8-Cl4 greater than 5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (13, SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.

  DOI：

  10.1021/jm00179a007
• 作为产物：
  描述：

  2,3-二氯苯甲醛 在 硫酸 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 7,8-二氯异喹啉
  参考文献：
  名称：

  Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines

  摘要：

  In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2 greater than 6,7,8-Cl3 greater than 7-Cl approximately 5,6,7,8-Cl4 greater than 5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (13, SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.

  DOI：

  10.1021/jm00179a007

文献信息

• Pharmaceutical compositions and methods of inhibiting phenylethanolamine
  申请人：SmithKline Corporation

  公开号：US03988339A1

  公开（公告）日：1976-10-26

  Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase using 7 and/or 8 substituted 1,2,3,4-tetrahydroisoquinoline compounds.

  制药组合物和使用7和/或8取代的1,2,3,4-四氢异喹啉化合物抑制苯乙醇胺N-甲基转移酶的方法。
• 7- and/or 8-Sulfur substituted 1,2,3,4-tetrahydroisoquinoline compounds
  申请人：SmithKline Corporation

  公开号：US04228170A1

  公开（公告）日：1980-10-14

  1,2,3,4-Tetrahydroisoquinoline compounds having 7- and/or 8-sulfur substituents are inhibitors of phenylethanolamine N-methyltransferase.

  具有7-和/或8-硫取代基的1,2,3,4-四氢异喹啉化合物是苯乙醇胺N-甲基转移酶的抑制剂。
• 7 AND 8-Halo substituted 1,2,3,4-tetrahydroisoquinoline compounds
  申请人：SmithKline Corporation

  公开号：US03939164A1

  公开（公告）日：1976-02-17

  1,2,3,4-Tetrahydroisoquinoline compounds having 7 and 8 halo substituents are inhibitors of phenylethanolamine N-methyltransferase.

  具有7和8个卤素取代基的1,2,3,4-四氢异喹啉化合物是苯乙醇胺N-甲基转移酶的抑制剂。
• Transition-State Analogues of Phenylethanolamine <i>N</i>-Methyltransferase
  作者：Niusha Mahmoodi、Rajesh K. Harijan、Vern L. Schramm

  DOI：10.1021/jacs.0c05446

  日期：2020.8.19

  of 12.0 nM. This is among the first TS analogue inhibitors of methyltransferase enzymes to show an affinity in the nanomolar range. Isothermal titration calorimetry (ITC) measurements indicated negative cooperative binding of inhibitor to the dimeric protein, driven by favorable entropic contributions. Structural analysis revealed that inhibitor 3 binds to hPNMT by filling the catalytic binding pockets

  苯乙醇胺 N-甲基转移酶 (PNMT) 是儿茶​​酚胺合成中的关键酶。它转移 S-腺苷甲硫氨酸 (SAM) 的甲基以催化去甲肾上腺素合成肾上腺素。肾上腺素与多种人类过程有关，包括调节血压和呼吸，以及在阿尔茨海默病中发现的神经变性。人类 PNMT (hPNMT) 通过 SN2 过渡态 (TS) 进行，其中甲基的转移是限速的。TS 类似物酶抑制剂对它们的目标具有特异性，并且比它们的底物结合更紧密的数量级。设计、合成了类似于 hPNMT TS 的分子，并对其进行了动力学表征。这种新的抑制支架旨在模仿 hPNMT TS 的几何形状和电子特性。合成努力产生了一种紧密结合的抑制剂，其 Ki 值为 12.0 nM。这是在纳摩尔范围内显示亲和力的首批甲基转移酶的 TS 类似物抑制剂之一。等温滴定量热法 (ITC) 测量表明抑制剂与二聚体蛋白的负协同结合，受有利的熵贡献驱动。结构分析表明，抑制剂 3 通过填充辅因子
• Non-natural nucleotides and dinucleotides
  申请人：——

  公开号：US20040122223A1

  公开（公告）日：2004-06-24

  Nucleotide derivatives of formula (1) are described: wherein: G is a hydrogen atom or an optionally substituted aliphatic, heteroaliphatic, cycloaliphatic, polycycloaliphatic, aromatic or heteroaromatic group or a non-natural nucleoside as defined herein; G′ is a non-natural necleoside as defined herein; n is zero, or the integer 1 or 2; m is zero or the integer 1 or 2; and the salts, solvates, hydrates and N-oxides thereof. The compounds are P2Y receptor agonists and are of use in the prophylaxis and treatment of diseases and disorders involving abnormal secretory mechanisms such as inadequate functioning of mucociliary clearance mechanisms or abnormal tear secretion or in the treatment of diseases involving inappropriate cellular glucose uptake.

  公式（1）的核苷酸衍生物被描述如下：其中：G是氢原子或可选择取代的脂肪，杂脂肪，环脂肪，多环脂肪，芳香或杂芳基团或非天然核苷酸，如此处所定义；G'是如此处所定义的非天然核苷酸；n为零或整数1或2；m为零或整数1或2；以及其盐，溶剂化合物，水合物和N-氧化物。这些化合物是P2Y受体激动剂，用于预防和治疗涉及异常分泌机制的疾病和障碍，如粘液纤毛清除机制功能不足或泪液分泌异常，或用于治疗涉及不适当的细胞葡萄糖摄取的疾病。