7-氯-N-(1-苯基乙基)喹啉-4-胺 | 1039994-08-5

• 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: 7-氯-N-(1-苯基乙基)喹啉-4-胺
• 英文名称: 7-chloro-N-(1-phenylethyl)quinolin-4-amine
• CAS: 1039994-08-5
• 化学式: C₁₇H₁₅ClN₂
• 分子量: 282.772
• InChiKey: UBBLKFCVKXJBRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 乙醚 、 7-氯-N-(1-苯基乙基)喹啉-4-胺 、 [PtCl₂(dppb)]*2H₂O 反应 24.0h， 以78.2%的产率得到[Pt(dppb)(Q-MOD-II)Cl]PF_6*1.5C₄H₁₀O
  参考文献：
  名称：

  Chiral Platinum(II) Complexes Featuring Phosphine and Chloroquine Ligands as Cytotoxic and Monofunctional DNA-Binding Agents

  摘要：

  Chiral molecules in nature are involved in many biological events; their selectivity and specificity make them of great interest for understanding the behavior of bioactive molecules, by providing information about the chiral discrimination. Inspired by these conformational properties, we present the design and synthesis of novel chiral platinum(II) complexes featuring phosphine and chloroquine ligands with the general formula [PtCl(P)(2)(CQ)]PF6 (where (P)(2) = triphenylphosphine (PPh3) (5), 1,3-bis-(diphenylphosphine)propane (dppp) (6), 1,4-bi-s(diphenylphosphine)butane (dppb) (7), 1,1'-bis-(diphenylphosphine)ferrocene (dppf) (8), and CQ = chloroquine] and their precursors of the type [PtCl2(P)(2)] are described. The complexes were characterized by elemental analysis, absorption spectroscopy in the infrared and ultraviolet-visible (UV-vis) regions, multinudear (H-1, C-13, P-31, N-15, and Pt-195) NMR spectroscopy, cyclic voltammetry, and mass spectrometry (in the case of chloroquine complexes). The interactions of the new platinum-chloroquine complexes with both albumin (BSA), using.fluorescence spectroscopy, and DNA, by four widely reported methods were also evaluated. These experiments showed that these Pt-CQ complexes interact strongly with DNA and have high affinities for BSA, in contrast to CQ and CQDP (chloroquine diphosphate), which interact wealdy with these biomolecules. Additional assays were performed in order to investigate the cytotoxicity of the platinum complexes against two healthy cell lines (mouse fibroblasts (L929) and the Chinese hamster lung (V79-4)) and four tumor cell lines (human breast (MDA-MB-231 and MCF-7), human lung (A549), and human prostate (DU-145)). The results suggest that the Pt-CQ complexes are generally more cytotoxic than the free CO2. showing that they are promising as anticancer drugs.

  DOI：

  10.1021/acs.inorgchem.5b01647
• 作为产物：
  描述：

  4,7-二氯喹啉 、 α-苯乙胺 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 7-氯-N-(1-苯基乙基)喹啉-4-胺
  参考文献：
  名称：

  [EN] AMINOQUINOLINIUM SALTS, METHODS OF THEIR PRODUCTION AND THEIR USE AS ACTIVE AGENTS FOR BIOTECHNOLOGICAL AND MEDICAL APPLICATIONS AGAINST BINARY TOXINS
  [FR] SELS D'AMINOQUINOLINE, LEURS PROCÉDÉS DE PRODUCTION ET LEUR UTILISATION EN TANT QU'AGENTS ACTIFS POUR DES APPLICATIONS BIOTECHNOLOGIQUES ET MÉDICALES CONTRE LES TOXINES BINAIRES

  摘要：

  本发明涉及氨基喹啉盐，其用途以及合成此类氨基喹啉盐的方法。此外，本发明涉及包含根据本发明的氨基喹啉盐的组合物。本发明涉及来自氨基喹啉化合物类的生物活性化合物，特别是它们对多种细菌的AB型二元毒素的抑制作用，如厌氧梭菌、肉毒梭菌和炭疽芽孢杆菌。该发明还涉及将这些氨基喹啉化合物用作药物，更具体地用作治疗细菌感染的药物，尤其是由产生二元型毒素的细菌引起的细菌感染。本发明还涉及根据本发明生产这些化合物的方法。

  公开号：

  WO2012041493A1

文献信息

• [EN] AMINOQUINOLINIUM SALTS, METHODS OF THEIR PRODUCTION AND THEIR USE AS ACTIVE AGENTS FOR BIOTECHNOLOGICAL AND MEDICAL APPLICATIONS AGAINST BINARY TOXINS<br/>[FR] SELS D'AMINOQUINOLINE, LEURS PROCÉDÉS DE PRODUCTION ET LEUR UTILISATION EN TANT QU'AGENTS ACTIFS POUR DES APPLICATIONS BIOTECHNOLOGIQUES ET MÉDICALES CONTRE LES TOXINES BINAIRES
  申请人：UNIV WUERZBURG J MAXIMILIANS

  公开号：WO2012041493A1

  公开（公告）日：2012-04-05

  The present invention relates to aminoquinoline salts, their uses and to methods of synthesizing such aminoquinoline salts. Moreover, the present invention relates to compositions comprising aminoquinoline salts in accordance with the present invention. The present invention relates to bioactive compounds from the class of aminoquinoline compounds, and in particular their inhibitory effects on the binary toxins of an AB-type of a number of bacteria, such as Clostridium perfringens, Clostridium botulinum, and Bacillus anthracis. The invention also relates to the use of these aminoquinoline compounds as drugs, more particularly as drugs for the treatment of bacterial infections, even more particularly bacterial infections caused by bacteria which produce pore forming toxins of a binary type. The present invention also relates to methods of producing the compounds in accordance with the present invention.

  本发明涉及氨基喹啉盐，其用途以及合成此类氨基喹啉盐的方法。此外，本发明涉及包含根据本发明的氨基喹啉盐的组合物。本发明涉及来自氨基喹啉化合物类的生物活性化合物，特别是它们对多种细菌的AB型二元毒素的抑制作用，如厌氧梭菌、肉毒梭菌和炭疽芽孢杆菌。该发明还涉及将这些氨基喹啉化合物用作药物，更具体地用作治疗细菌感染的药物，尤其是由产生二元型毒素的细菌引起的细菌感染。本发明还涉及根据本发明生产这些化合物的方法。
• Chiral Platinum(II) Complexes Featuring Phosphine and Chloroquine Ligands as Cytotoxic and Monofunctional DNA-Binding Agents
  作者：Wilmer Villarreal、Legna Colina-Vegas、Clayton Rodrigues de Oliveira、Juan C. Tenorio、Javier Ellena、Fábio C. Gozzo、Marcia Regina Cominetti、Antonio G. Ferreira、Marco Antonio Barbosa Ferreira、Maribel Navarro、Alzir A. Batista

  DOI：10.1021/acs.inorgchem.5b01647

  日期：2015.12.21

  Chiral molecules in nature are involved in many biological events; their selectivity and specificity make them of great interest for understanding the behavior of bioactive molecules, by providing information about the chiral discrimination. Inspired by these conformational properties, we present the design and synthesis of novel chiral platinum(II) complexes featuring phosphine and chloroquine ligands with the general formula [PtCl(P)(2)(CQ)]PF6 (where (P)(2) = triphenylphosphine (PPh3) (5), 1,3-bis-(diphenylphosphine)propane (dppp) (6), 1,4-bi-s(diphenylphosphine)butane (dppb) (7), 1,1'-bis-(diphenylphosphine)ferrocene (dppf) (8), and CQ = chloroquine] and their precursors of the type [PtCl2(P)(2)] are described. The complexes were characterized by elemental analysis, absorption spectroscopy in the infrared and ultraviolet-visible (UV-vis) regions, multinudear (H-1, C-13, P-31, N-15, and Pt-195) NMR spectroscopy, cyclic voltammetry, and mass spectrometry (in the case of chloroquine complexes). The interactions of the new platinum-chloroquine complexes with both albumin (BSA), using.fluorescence spectroscopy, and DNA, by four widely reported methods were also evaluated. These experiments showed that these Pt-CQ complexes interact strongly with DNA and have high affinities for BSA, in contrast to CQ and CQDP (chloroquine diphosphate), which interact wealdy with these biomolecules. Additional assays were performed in order to investigate the cytotoxicity of the platinum complexes against two healthy cell lines (mouse fibroblasts (L929) and the Chinese hamster lung (V79-4)) and four tumor cell lines (human breast (MDA-MB-231 and MCF-7), human lung (A549), and human prostate (DU-145)). The results suggest that the Pt-CQ complexes are generally more cytotoxic than the free CO2. showing that they are promising as anticancer drugs.