6-氯-2-甲基-4-羟基喹啉 | 15644-86-7

• 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 - 喹啉及其衍生物
• 中文名称: 6-氯-2-甲基-4-羟基喹啉
• 中文别名: 6-氯-2-甲基喹啉-4-醇；6-氯-4-羟基-2-甲基喹啉
• 英文名称: 6-chloro-2-methyl-quinolin-4-ol
• 英文别名: 6-chloro-2-methyl-1H-quinolin-4-one
• CAS: 15644-86-7
• 化学式: C₁₀H₈ClNO
• mdl: MFCD00023981
• 分子量: 193.633
• InChiKey: VGDMRXDQWBBKBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险类别码：
  R41
• 海关编码：
  2933499090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 6-Chloro-2-methylquinolin-4-ol
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 6-Chloro-2-methylquinolin-4-ol
CAS number: 15644-86-7

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C10H8ClNO
Molecular weight: 193.6

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-氯-2-甲基-4-羟基喹啉 在 三氯氧磷 作用下， 反应 26.0h， 生成 N¹-(6-chloro-2-methylquinolin-4-yl)-N²,N²-dimethylethane-1,2-diamine
  参考文献：
  名称：

  6-氯-2-芳基乙烯基喹啉的合成、构效关系及抗疟作用。

  摘要：

  迫切需要开发新的有效抗疟药来解决新出现的耐药性临床病例。我们之前的表型筛选将苯乙烯基喹啉UCF501鉴定为一种有前途的抗疟化合物。为了优化UCF501，我们在此报告了 2-芳基乙烯基喹啉的详细构效关系研究，从而发现了针对恶性疟原虫CQ 抗性 Dd2 菌株的有效、低纳摩尔抗疟原虫化合物，具有出色的选择性（抗性指数 < 1 和选择性指数 > 200）。几种代谢稳定的 2-芳基乙烯基喹啉被鉴定为在滋养体阶段杀死无性血液阶段寄生虫的速效剂，以及最有希望的化合物24还展示了传输阻塞的潜力。此外，24的单磷酸盐在小鼠模型中表现出优异的体内抗疟功效，而没有明显的毒性。因此，2-芳基乙烯基喹啉代表了一类有前途的抗疟药物先导。

  DOI：

  10.1021/acs.jmedchem.0c00858
• 作为产物：
  描述：

  3-(4-氯苯胺基)巴豆酸乙酯 在 二苯醚 作用下， 生成 6-氯-2-甲基-4-羟基喹啉
  参考文献：
  名称：

  通过全细胞生物转化生成 Aurachin 衍生物及其抗原生动物特性评价。

  摘要：

  天然产物金鱼草素 D 是一种法尼基化喹诺酮生物碱，已知其具有抗疟疾病原体疟原虫属的活性。在这项研究中，我们表明金鱼草素 D 也能抑制其他寄生原生动物。虽然 aurachin D 对布氏锥虫罗得西亚锥虫只有适度的影响，但在体外试验中，另外两种锥虫，克氏锥虫和杜氏利什曼原虫，分别在低微摩尔和纳摩尔浓度下被杀死。经测定，aurachin D 的 IC50 值甚至低于参比药物苯并咪唑和米替福新的 IC50 值。由于这些有希望的结果，我们着手探索结构修饰对这种天然产物生物活性的影响。为了生成在 C-2 具有不同取代基的金鱼草素 D 衍生物，喹诺酮环系统的 C-6 和 C-7 位置，我们使用能够进行金黄色素型异戊二烯化的重组大肠杆菌菌株进行全细胞生物转化。将具有甲基、甲氧基和卤素基团的喹诺酮前体分子喂入该大肠杆菌菌株，该菌株将底物转化为所需的类似物。与 aurachin D 相比，所生成的衍生物均未表

  DOI：

  10.3390/molecules28031066

文献信息

• 4-Substituted Thioquinolines and Thiazoloquinolines: Potent, Selective, and Tween-80 in vitro Dependent Families of Antitubercular Agents with Moderate in vivo Activity
  作者：Jaime Escribano、Cristina Rivero-Hernández、Hilda Rivera、David Barros、Julia Castro-Pichel、Esther Pérez-Herrán、Alfonso Mendoza-Losana、Íñigo Angulo-Barturen、Santiago Ferrer-Bazaga、Elena Jiménez-Navarro、Lluís Ballell

  DOI：10.1002/cmdc.201100309

  日期：2011.12.9

  Two new families of closely related selective, non‐cytotoxic, and potent antitubercular agents were discovered: thioquinolines and thiazoloquinolines. The compounds were found to possess potent antitubercular properties in vitro, an activity that is dependent on experimental conditions of MIC determination (resazurin test and the presence or absence of Tween‐80). To clarify the therapeutic potential

  发现了两个密切相关的选择性，非细胞毒性和有效抗结核药的新家族：硫喹啉和噻唑啉喹啉。发现这些化合物在体外具有有效的抗结核特性，其活性取决于MIC测定的实验条件（刃天青测试和是否存在Tween-80）。为了阐明这些化合物家族的治疗潜能，人们进行了化学化学努力以生成类似铅的结构，从而可以进行鼠药功效研究并帮助阐明体外观察的体内意义。尽管最终化合物在小鼠中仅显示出有限的全身暴露水平，但在无毒剂量下观察到了适中的体内功效水平。
• Synthesis and identification of quinoline derivatives as topoisomerase I inhibitors with potent antipsoriasis activity in an animal model
  作者：Wen-Jin Zhang、Peng-Hui Li、Min-Cong Zhao、Yao-Hao Gu、Chang-Zhi Dong、Hui-Xiong Chen、Zhi-Yun Du

  DOI：10.1016/j.bioorg.2019.03.073

  日期：2019.7

  and effective strategies for the treatment of this condition remains important. Research suggests that DNA topoisomerase I (Topo I) inhibitors may have potent psoriasis-ameliorating effects. Here, 25 quinoline derivatives were synthesized and identified as Topo I inhibitors. These compounds inhibited the 12-O-tetradecanoylphorbol-13-acetate-induced mouse ear inflammation. The most potent analogs, 5i and

  牛皮癣是一种慢性炎症和免疫介导的皮肤病。尽管某些药物已显示出在治疗牛皮癣方面的临床成功，但是开发安全有效的治疗该病的策略仍然很重要。研究表明，DNA拓扑异构酶I（Topo I）抑制剂可能具有有效的改善牛皮癣的作用。在这里，合成了25种喹啉衍生物并将其鉴定为Topo I抑制剂。这些化合物抑制了12-O-十四烷酰phorbol-13-乙酸盐诱导的小鼠耳朵发炎。最有效的类似物5i和5l抑制了脂多糖刺激的HaCaT细胞中炎性细胞因子的表达。另外，先导化合物显着改善了小鼠咪喹莫特诱发的牛皮癣样炎症。此外，细胞因子和炎性介质的表达水平 白细胞介素（IL）-17A，IL-22，IL-23，核因子-κB亚基p65，肿瘤坏死因子-α和干扰素-γ等在5i和5l处理的小鼠的背部皮肤中被显着抑制。这些发现表明，Topo I活性的抑制可能是牛皮癣治疗的有效策略。
• Neue 4-Chinolinol- und 5,6,7,8-Tetrahydro-4-chinolinol-abkömmlinge mit biozider Wirkung
  作者：Horst Gildemeister、Harald Knorr、Hilman Mildenberger、Gerhard Salbeck

  DOI：10.1002/jlac.198219820908

  日期：1982.9.17

  Es wird die Synthese einiger O-substituierter 4-Chinolinole und 5,6,7,8-Tetrahydro-4-chinolinole 7–13 beschrieben. Ausgehend von 2 und 4 gelangt man mit POCl3 zu 4-Chlorchinolinen 14 und 15, welche in die 4-Aryloxychinoline 16 und 17 sowie 4-Alkyl-(Aryl-)thiochinoline 20 bzw. 4-Aminochinoline 21 übergeführt werden.

  描述了一些O-取代的4-喹啉醇和5,6,7,8-四氢-4-喹啉醇7-13的合成。从2和4开始，POCl 3产生4-氯喹啉14和15，它们分别被转化为4-芳氧基喹啉16和17和4-烷基（芳基）硫代喹啉20和4-氨基喹啉21。
• Design, Synthesis and anti-HIV-1 Activity of Modified Styrylquinolines
  作者：Shivani Mahajan、Shiv Gupta、Nisha Jariwala、Deepali Bhadane、Late K.K. Bhutani、Smita Kulkarni、Inder Pal Singh

  DOI：10.2174/1570180815666171212143339

  日期：2018.7.16

  the synthesis of novel compounds based on naturally occurring scaffolds and their evaluation as potential anti-HIV agents. Objective: Design and synthesis of styrylquinoline scaffold based new molecules and evaluation of their anti-HIV-1 activity. Methods: A series of forty three new styrylquinolines (SQLs) was designed and synthesized. The newly synthesized compounds were tested for anti-HIV-1 activity

  背景：耐药性和潜在的病毒感染库已经阻止了HIV病毒的彻底根除，这凸显了在发现新的抗HIV药物方面需要不断努力的必要。本研究涉及基于天然支架的新型化合物的合成及其作为潜在抗HIV药物的评估。 目的：基于苯乙烯基喹啉骨架的新分子的设计，合成及其抗HIV-1活性的评价。 方法：设计并合成了四十三种新的苯乙烯基喹啉（SQL）。测试了新合成的化合物对TZM-b1细胞系中HIV-1VB59和HIV-1UG070主要分离株的抗HIV-1活性。 结果：最具活性的化合物9和34（IC50 = 0.5-4.0 µM）对PBMC中的HIV-1VB51初次分离株也表现出显着的抑制活性（IC50 = 7.3 µM）。还发现化合物9和34抑制HIV-1进入宿主细胞和融合抑制活性。该研究鼓励进一步探索SQL核以设计抗HIV-1药物。 结论：该研究鼓励进一步探索SQL核以设计抗HIV-1药物。
• NaHSO₄/SiO₂: An Efficient Catalyst for the Synthesis of β-Enaminones and 2-Methylquinolin-4(1H)-Ones under Solvent-Free Condition
  作者：Suryakant B. Sapkal、Kiran F. Shelke、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.5012/jkcs.2010.54.6.723

  日期：2010.12.20

  An efficient and simplified protocol for NaHSO 4 /SiO 2 catalyzed solvent-free synthesis of β-enaminone and 2-methyl-quinolin-4( 1H)-one derivatives under microwave irradiation is described. A series of functionalized derivatives have been synthesized in shorter reaction times with moderate to good yields. The use of milder catalyst in non-conventional method offers significant advantages over conventional

  描述了一种在微波辐射下NaHSO 4 / SiO 2催化的β-烯胺酮和2-甲基-喹啉-4（1H）-one衍生物的无溶剂合成的有效且简化的方案。已经以较短的反应时间合成了一系列官能化衍生物，具有中等至良好的产率。与常规方法相比，在非常规方法中使用温和的催化剂具有明显的优势，例如更高的选择性，简便性，无溶剂反应和非环境污染条件。

表征谱图