7-氯-4-(1-哌嗪基)喹啉 | 837-52-5

• 物质功能分类: 医药中间体 - 哌嗪类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 7-氯-4-(1-哌嗪基)喹啉
• 中文别名: 7-氯-4-哌嗪基喹啉；7-氯-4-哌嗪-1-基喹啉
• 英文名称: 7-chloro-4-piperazinylquinoline
• 英文别名: 7-chloro-4-(piperazin-1-yl)quinoline；7-chloro-4-(1-piperazinyl)quinoline；7-chloro-4-(piperazine-1-yl)quinoline；4-piperazinyl-7-chloroquinoline；7-chloro-4-piperazin-1-ylquinoline
• CAS: 837-52-5
• 化学式: C₁₃H₁₄ClN₃
• mdl: MFCD01476123
• 分子量: 247.727
• InChiKey: DNXNPMDUDGUXOB-UHFFFAOYSA-N

物化性质

• 熔点：
  113-116
• 沸点：
  433.5±35.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微）、DMSO（轻微）、甲醇（非常轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  C
• 危险类别码：
  R34
• 海关编码：
  2933990090
• 安全说明：
  S22,S26,S36/37/39,S45
• WGK Germany：
  3
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,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: 7-Chloro-4-piperazin-1-yl-quinoline
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-Chloro-4-piperazin-1-yl-quinoline
CAS number: 837-52-5

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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: C13H14ClN3
Molecular weight: 247.7

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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

制备方法与用途

化学性质：液体化合物。

用途：作为喹哌磷酸盐的中间体。

生产方法：通过将4,7-二氯喹啉与六水哌嗪加热缩合而制得。

反应信息

• 作为反应物：
  描述：

  7-氯-4-(1-哌嗪基)喹啉 在 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 7-chloro-4-(4-(3-((7-chloroquinolin-4-yl)oxy)propyl)piperazin-1-yl)quinoline
  参考文献：
  名称：

  Bhovi, Manjunath G.; Tanwar, Pooja; Yadav, Gyan Chand, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 215 - 220

  摘要：

  DOI：
• 作为产物：
  描述：

  7-氯-4-羟基喹啉 在 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 22.0h， 生成 7-氯-4-(1-哌嗪基)喹啉
  参考文献：
  名称：

  带有1,2,4-恶二唑基团的新喹啉衍生物的合成，抗结核研究和生物学评估

  摘要：

  结核病是由结核分枝杆菌（Mtb）引起的传染病，它是全世界每年死亡人数最多的原因。在此，设计和合成了二十一种新的取代的1,2,4-恶二唑-3-基甲基-哌嗪-1-基-喹啉衍生物，并通过多步合成，然后对其抗Mtb WT H37Rv的抗结核潜力进行了体外评估。发现化合物QD-18的MIC值为0.5 µg / ml很有前景，而QD-19至QD-21的MIC值为0.25 µg / ml也很引人注目。此外，我们进行了实验，以确认这些化合物的代谢稳定性，细胞毒性和药代动力学，以及对它们的杀灭动力学。QD-18。发现这些化合物是口服生物利用的并且是高度有效的。总而言之，这些结果表明QD-18，QD-19，QD-20和QD-21是用于开发新型化学类抗结核药物的有前途的先导化合物。

  DOI：

  10.1016/j.bmcl.2018.11.002

文献信息

• New N-Mannich bases obtained from isatin and piperazine derivatives: the synthesis and evaluation of antimicrobial activity
  作者：Andrei V. Bogdanov、Al’bina M. Vazykhova、Nadezhda R. Khasiyatullina、Dmitry B. Krivolapov、Alexey B. Dobrynin、Alexandra D. Voloshina、Vladimir F. Mironov

  DOI：10.1007/s10593-016-1826-6

  日期：2016.1

  A Mannich reaction of isatin with monosubstituted piperazines in the presence of aqueous formaldehyde was used to synthesize new, as well as two previously described derivatives of 1-piperazinomethylisatins, which were further converted to isoindigo derivatives. The antimicrobial activity of the obtained heterocycles was evaluated.

  在含水甲醛的存在下，靛红与单取代的哌嗪的曼尼希反应用于合成新的以及先前描述的1-哌嗪子甲基靛红的两种衍生物，然后将其进一步转化为异靛蓝衍生物。评价得到的杂环的抗菌活性。
• [EN] SUBSTITUTED QUINOLINE CCR5 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR CCR5 A BASE DE QUINOLEINE SUBSTITUES
  申请人：SCHERING AG

  公开号：WO2004002960A1

  公开（公告）日：2004-01-08

  The present invention relates to CCR5 receptor antagonists of formulae (1a) or (1b), enantiomers, diastereomers, salts and solvates thereof wherein R1, R2, R3, R4, R5, and R7 are as defined herein. The invention further includes a method of CCR5-mediated disorders employing such compounds.

  本发明涉及式（1a）或（1b）的CCR5受体拮抗剂，其对映体、二对映体、盐和溶剂合物，其中R1、R2、R3、R4、R5和R7如本文所定义。该发明还包括一种利用这些化合物治疗CCR5介导的疾病的方法。
• Alkylated/aminated nitroimidazoles and nitroimidazole-7-chloroquinoline conjugates: Synthesis and anti-mycobacterial evaluation
  作者：Shalini、Albertus Viljoen、Laurent Kremer、Vipan Kumar

  DOI：10.1016/j.bmcl.2018.03.021

  日期：2018.5

  The success in exploring anti-tubercular potency of nitroimidazole and quinoline, the core moieties of recently approved anti-tubercular drugs instigated us to synthesize a series of alkylated/aminated 2-methyl-5-nitroimidazoles and nitroimidazole-7-chloroquinoline conjugates and to evaluate them for their activities against Mycobacterium tuberculosis as well as for their cytotoxicity towards the J774

  探索硝基咪唑和喹啉抗结核药的成功，是最近批准的抗结核药的核心部分，促使我们合成了一系列烷基化/胺化的2-甲基-5-硝基咪唑和硝基咪唑-7-氯喹啉共轭物，并进行了评估它们具有抗结核分枝杆菌的活性以及对J774鼠巨噬细胞系的细胞毒性。尽管合成的化合物没有超过标准药物异烟肼的活性，但它们具有明显的活性，且细胞毒性最小。合成的以丁基链为连接基的硝基咪唑-7-氯喹啉共轭物11c被证明是该系列中最有效的化合物，MIC 50值为2.2μg/ mL。
• Design, Synthesis and Study of Antibacterial and Antitubercular Activity of Quinoline Hydrazone Hybrids
  作者：Shruthi T G、Sangeetha Subramanian、Sumesh Eswaran

  DOI：10.1515/hc-2020-0109

  日期：2020.10.15

  various infections. Therefore, the search for antimicrobials is a never-ending task. Hydrazones and quinolines possess a wide variety of biological activities. Herewith, eleven quinoline hydrazone derivatives have been designed, synthesized, characterized and evaluated for their antibacterial activity and antitubercular potential against Mtb WT H37Rv. Compounds QH-02, QH-04 and QH-05 were found to be

  摘要 新出现的细菌耐药性给各种感染的治疗带来了广泛的问题。因此，寻找抗菌药物是一项永无止境的任务。腙和喹啉具有多种生物活性。因此，已经设计、合成、表征和评估了 11 种喹啉腙衍生物的抗菌活性和对 Mtb WT H37Rv 的抗结核潜力。发现化合物 QH-02、QH-04 和 QH-05 是有前途的化合物，对 Mtb WT H37Rv 的 MIC 值为 4 μg/mL。还发现化合物 QH-02、QH-04、QH-05 和 QH-11 对包括鲍曼不动杆菌、大肠杆菌和金黄色葡萄球菌在内的细菌菌株具有活性。更多，
• Discovery of a Novel CCR5 Antagonist Lead Compound Through Fragment Assembly
  作者：Yanqing Liu、Enkun Zhou、Kunqian Yu、Jin Zhu、Yu Zhang、Xin Xie、Jian Li、Hualiang Jiang

  DOI：10.3390/molecules13102426

  日期：——

  CCR5, as the major co-receptor for HIV-1 entry, is an attractive novel target for the pharmaceutical industry in the HIV-1 therapeutic area. In this study, based on the structures of maraviroc and 1,4-bis(4-(7-chloroquinolin-4-yl)piperazin-1-yl)butane-1,4-dione (1), which was identified using structure-based virtual screening in conjunction with a calcium mobilization assay, a series of novel small molecule CCR5 antagonists have been designed and synthesized through fragment assembly. Preliminary SARs were obtained, which are in good agreement with the molecular binding model and should prove helpful for future antagonist design. The novel scaffold presented here might also be useful in the development of maraviroc-derived second generation CCR5 antagonists.

  CCR5作为HIV-1入侵的主要共受体，是制药工业在HIV-1治疗领域的一个具有吸引力的新型靶点。本研究基于马拉韦罗克和1，4-双(4-(7-氯喹啉-4-基)哌嗪-1-基)丁烷-1，4-二酮(1)的结构，通过片段组装设计并合成了一系列新型小分子CCR5拮抗剂，其中1是通过结构虚拟筛选结合钙动员测定鉴定的。初步的SARs(构效关系)得以获得，这些SARs与分子结合模型吻合良好，有望对未来拮抗剂设计具有指导意义。本文所展示的新型骨架在开发由马拉韦罗克衍生的第二代CCR5拮抗剂中可能还有用武之地。