4-(3-methyl-5-trifluoromethyl-1H-pyrazol-1-yl)-7-chloroquinoline | 193203-45-1

• 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
• 英文名称: 4-(3-methyl-5-trifluoromethyl-1H-pyrazol-1-yl)-7-chloroquinoline
• 英文别名: 7-Chloro-4-[3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl]quinoline；7-chloro-4-[3-methyl-5-(trifluoromethyl)pyrazol-1-yl]quinoline
• CAS: 193203-45-1
• 化学式: C₁₄H₉ClF₃N₃
• 分子量: 311.694
• InChiKey: QCGYFYDSSBUJMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  409.9±45.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三氟乙酰丙酮 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 4-(3-methyl-5-trifluoromethyl-1H-pyrazol-1-yl)-7-chloroquinoline
  参考文献：
  名称：

  Reaction of hydrazinoquinolines with trifluoromethyl-β-diketones: structural and mechanistic studies

  摘要：

  Reaction of 2-hydrazino-4-methylquinoline with a series of trifluoromethyl-beta-diketones gives 3-substituted-5-hydroxy-1-(4-methylquinolin-2-yl)-5-trifluoromethyl-4,5-dihydropyrazoles and, in some cases, 5-substituted-1-(4-methylquinolin-2-yl)depending on the substitution of the diketone. Dehydration of the hydroxydihydropyrazoles can be effected with sulphuric acid in acetic acid to give the regioisomeric 3-substituted-1-(4-methylquinolin-2-yl)-5-trifluoromethylpyrazoles. In contrast, the reaction of two 4-hydrazinoquinolines with 1,1,1-trifluoropentane-2,4-dione afforded a different isolable intermediate, the corresponding hydrazone formed at the 4-carbonyl. Dehydration gave the 1-(substituted-quinolin-4-yl)-3-methyl-5-trifluoromethylpyrazoles. The regioisomeric identity of the pyrazoles was established using F-19 NMR. (C) Elsevier Science S.A.

  DOI：

  10.1016/s0022-1139(96)03570-1

文献信息

• Antimalarial activity of 4-(5-trifluoromethyl-1H-pyrazol-1-yl)-chloroquine analogues
  作者：Wilson Cunico、Cleber A. Cechinel、Helio G. Bonacorso、Marcos A.P. Martins、Nilo Zanatta、Marcus V.N. de Souza、Isabela O. Freitas、Rodrigo P.P. Soares、Antoniana U. Krettli

  DOI：10.1016/j.bmcl.2005.10.033

  日期：2006.2

  the eight (4,5-dihydropyrazol-1-yl) chloroquine 2 derivatives tested showed a significant activity in vitro, thus, are a promising new class of antimalarials. The three most active ones were also tested in vivo against Plasmodium berghei in mice. However, the (pyrazol-1-yl) chloroquine 3 derivatives were mostly inactive, suggesting that the aromatic functionality of the pyrazole ring was critical.

  由1,1,1-三氟-4-甲氧基-3-烯丙基-2-酮与4-肼基-7-氯喹啉反应合成的氯喹吡唑类似物的抗疟活性已在体外针对氯喹进行了评估。抗性恶性疟原虫克隆。与没有药物的对照相比，通过掺入[（3）H]次黄嘌呤来测量存在试验药物的寄生虫的生长。测试的八种（4,5-二氢吡唑-1-基）氯喹2衍生物中，除一种化合物外，其他化合物均在体外具有显着活性，因此是一类有前途的新型抗疟药。还在小鼠中对三种活性最强的伯氏疟原虫进行了体内测试。然而，（吡唑-1-基）氯喹3衍生物大部分是无活性的，这表明吡唑环的芳族官能度是关键的。
• An efficient and regiospecific preparation of trifluoromethyl substituted 4-( 1<i>H</i>-pyrazol-1 -yl)-7-chloroquinolines
  作者：Helio G. Bonacorso、Cleber A. Cechinel、Marli R. Oliveira、Michelle B. Costa、Marcos A. P. Martins、Nilo Zanatta、Alex F. C. Flores

  DOI：10.1002/jhet.5570420604

  日期：2005.9

  A new series of 4-[3-alkyl(aryl)(heteroaryl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl]-7-chloroquinolines, where [alkyl = CH3; aryl = C6H5, 4-CH3C6H4, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-CH3OCgH4, 4-NO2CgH4, 4-biphenyl, 1-naphthyl; heteroaryl = 2-furyl and 2-thienyl] has been regiospecifi-caly obtained from the reaction of 7-chloro-4-hydrazinoquinoline with 4-substituted-l,1,1-trifluoro-

  一系列新的4- [3-烷基（芳基）（杂芳基）-5-羟基-5-三氟甲基-4,5-二氢-1 H-吡唑-1-基] -7-氯喹啉，其中[烷基= CH 3；芳= C 6 H ^ 5，4-CH 3 C ^ 6 ħ 4，4-FC 6 H ^ 4，4-CLC 6 ħ 4，4- BRC 6 ħ 4，4-CH 3 OCgH 4，4-NO 2 CGH 4，4-联苯基，1-萘基；杂芳基＝ 2-呋喃基和2-噻吩基]是由7-氯-4-肼基喹啉与4-取代的-1,1,1-三氟-4-甲氧基丁-3-en-2-的反应在区域上确定的。收率为61-96％。随后，在酸性条件下4,5-二氢吡喃-唑基喹啉的脱水反应在73-96中提供了一系列新的4-（3-取代的5-三氟甲基-1 H-吡唑-基-1-基）-7-氯喹啉。 ％ 屈服。