6-(三氟甲基)-8-喹啉胺 | 955413-26-0

• 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-(三氟甲基)-8-喹啉胺
• 中文别名: 6-三氟甲基-8-喹啉胺
• 英文名称: 6-(trifluoromethyl)quinolin-8-amine
• CAS: 955413-26-0
• 化学式: C₁₀H₇F₃N₂
• 分子量: 212.174
• InChiKey: OWBHAJLHWDFULE-UHFFFAOYSA-N

物化性质

• 沸点：
  315.3±42.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 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：
  38.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  6-(三氟甲基)-8-喹啉胺 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.17h， 生成 6-(trifluoromethyl)-N-(pyrazolo[1,5-a]pyrimidin-7-yl)quinolin-8-amine
  参考文献：
  名称：

  Synthesis and in vitro evaluation of novel 8-aminoquinoline–pyrazolopyrimidine hybrids as potent antimalarial agents

  摘要：

  In the search of novel chemotherapeutic agents for emerging drug resistant parasites, the hybridization approaches have successfully emerged as an efficient tool in malarial chemotherapy. Herein, a rational design and synthesis of novel 8-aminoquinoline and pyrazolopyrimidine hybrids and their antimalarial activity against wild type Plasmodium falciparum (Pf_NF54) and resistant strain (Pf_K1) is reported. The medicinal chemistry approach to expand the scope of this series resulted in an identification of potent compounds with nanomolar potency (best IC50 5-10 nM). Systematic structure activity relationship (SAR) studies revealed that pyrazolopyrimidine and 8-aminoquinoline ring are essential for achieving good P. falciparum potency. The docking study revealed that the compound 6 can retain some of the critical interactions within pfDHODH drug target. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.003
• 作为产物：
  描述：

  4-氨基-3-硝基三氟甲苯 在 盐酸 、 tin(II) chloride dihdyrate 、 硫酸 、 arsenic pentoxide pentahydrate 作用下， 以 水 为溶剂， 反应 8.83h， 生成 6-(三氟甲基)-8-喹啉胺
  参考文献：
  名称：

  使用Skraup和Doebner-von Miller反应的温和型合成含氟1,10-菲咯啉

  摘要：

  描述了合成具有含氟基团的新的1,10-菲咯啉衍生物的通用途径。基于不同的氟化苯胺作为起始原料，进行Skraup反应的产率为19到48％，总产率为5到13％。合成了十个以前未知的衍生物，并通过NMR光谱（1 H，13 C，19 F），ESI质谱和元素分析对其进行了表征。

  DOI：

  10.1016/j.jfluchem.2016.11.016

文献信息

• Novel small molecules with selective cytotoxicity against human microvascular endothelial cell proliferation
  申请人：Kane L. John

  公开号：US20070254894A1

  公开（公告）日：2007-11-01

  Disclosed herein are angiogenesis inhibitors represented by formula (I) or formula (II): The variables for formulas (I) and (II) are defined herein.

  本文披露了由式(I)或式(II)表示的抑制血管生成的药物： 式(I)和式(II)中的变量在本文中有定义。
• Ni‐Catalyzed Direct Carboxylation of Aryl C−H Bonds in Benzamides with CO ₂
  作者：Chunzhe Pei、Jiarui Zong、Bin Li、Baiquan Wang

  DOI：10.1002/adsc.202101285

  日期：2022.2

  The direct carboxylation of inert aryl C−H bond catalyzed by abundant and cheap nickel is still facing challenge. Herein, we report the Ni-catalyzed direct carboxylation of aryl C−H bonds in benzamides under 1 atm of CO2 to afford various methyl carboxylates or phthalimides, dealing with different post-processing. The reaction displays excellent functional group tolerance and affords moderate to high

  丰富且廉价的镍催化惰性芳基 C-H 键直接羧化仍面临挑战。在此，我们报道了在 1 个大气压的 CO 2下 Ni 催化的苯甲酰胺中芳基 C-H 键的直接羧化反应，得到各种羧酸甲酯或邻苯二甲酰亚胺，并进行了不同的后处理。该反应表现出优异的官能团耐受性，并在温和条件下提供中等至高的羧化产率。详细的机理研究表明，Ni(0)-Ni(II)-Ni(I) 催化循环可能参与该反应。
• [EN] QUINOLINYL-PYRAZINE-CARBOXAMIDE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE QUINOLINYL-PYRAZINE-CARBOXAMIDE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2020132459A1

  公开（公告）日：2020-06-25

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quinolinyl-pyrazine-carboxamide (or similar) structure which function as activators of the cholesterol biosynthesis pathway within cancer cells and/or immune cells, which function as activators of the cell cycle regulation pathway within cancer cells and/or immune cells, and which function as up-regulators of HMGCS1 protein expression within cancer cells and/or immune cells, and which function as effective therapeutic agents for treating, ameliorating, and preventing various forms of cancer and other inflammatory disease.

  这项发明属于药物化学领域。具体来说，该发明涉及一类新型小分子，其具有喹啉基-吡嗪-羧酰胺（或类似）结构，其在癌细胞和/或免疫细胞内作为胆固醇生物合成途径的激活剂，作为癌细胞和/或免疫细胞内细胞周期调控途径的激活剂，作为癌细胞和/或免疫细胞内HMGCS1蛋白表达的上调剂，以及作为治疗、改善和预防各种癌症和其他炎症性疾病的有效治疗剂。
• Design and Synthesis of Orally Active Quinolyl Pyrazinamides as Sigma 2 Receptor Ligands for the Treatment of Pancreatic Cancer
  作者：Joyeeta Roy、Armita Kyani、Maha Hanafi、Yibin Xu、John Takyi-Williams、Duxin Sun、Essam Eldin A. Osman、Nouri Neamati

  DOI：10.1021/acs.jmedchem.2c01769

  日期：2023.2.9

  (σ2R) is overexpressed in select cancers and is regarded as a biomarker for tumor proliferation. σ2R ligands are emerging as promising theranostics for cancer and neurodegenerative diseases. Herein, we describe the design and synthesis of a series of novel quinolyl pyrazinamides as selective and potent σ2R ligands that show sub-micromolar potency in pancreatic cancer cell lines. Compounds 14 (JR1-157)

  Sigma 2 受体 (σ2R) 在某些癌症中过度表达，被视为肿瘤增殖的生物标志物。 σ2R 配体正在成为癌症和神经退行性疾病的有前途的治疗诊断剂。在此，我们描述了一系列新型喹啉基吡嗪酰胺的设计和合成，作为选择性和有效的 σ2R 配体，在胰腺癌细胞系中显示出亚微摩尔效力。化合物14 (JR1-157) 和17 (JR2-298) 结合 σ2R， K i分别为 47 和 10 nM。重要的是，化合物14的口服生物利用度为60%，在同基因胰腺癌模型中显示出显着的体内疗效，且没有明显的毒性。喹啉吡嗪酰胺的细胞毒性在铜存在下显着增强，而在铜螯合剂四硫代钼酸盐存在下减弱。总之，化合物14是水溶性的、代谢稳定的、口服活性的，并且增加自噬标记物LC3B的表达，并且值得进一步开发用于治疗胰腺癌。
• Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway
  作者：Chiranjit Sen、Tapan Sahoo、Harshvardhan Singh、Eringathodi Suresh、Subhash Chandra Ghosh

  DOI：10.1021/acs.joc.9b00942

  日期：2019.8.16

  An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ^•CBr₃ radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.