N-<2-(dimethylamino)ethyl>-2-(4-fluorophenyl)quinolin-4-amine | 133671-46-2

• 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: N-<2-(dimethylamino)ethyl>-2-(4-fluorophenyl)quinolin-4-amine
• 英文别名: N-[2-(dimethylamino)ethyl]-2-(4-fluorophenyl)quinolin-4-amine；1,2-Ethanediamine, N'-(2-(4-fluorophenyl)-4-quinolinyl)-N,N-dimethyl-；N-[2-(4-fluorophenyl)quinolin-4-yl]-N',N'-dimethylethane-1,2-diamine
• CAS: 133671-46-2
• 化学式: C₁₉H₂₀FN₃
• 分子量: 309.386
• InChiKey: WUUSWESBGKCYHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  哌啶 、 N-<2-(dimethylamino)ethyl>-2-(4-fluorophenyl)quinolin-4-amine 在 正丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 20.5h， 以40%的产率得到N,N-Dimethyl-N'-[2-(4-piperidin-1-yl-phenyl)-quinolin-4-yl]-ethane-1,2-diamine
  参考文献：
  名称：

  取代的2-苯基喹啉-4-胺的合成和活性，它们是免疫刺激性CpG-寡脱氧核苷酸的拮抗剂。

  摘要：

  合成了在喹啉的苯基和C4处取代的57个2-苯基喹啉，并分析了其对具有CpG基序的寡脱氧核苷酸的免疫刺激作用的抑制作用。经典Free-Wilson分析的Fujita-Ban变体对一系列48个相对较小的分子给出了高度显着的相关性，表明（i）取代基对生物活性的部分贡献（EC（50））是加和的（ii）假设所研究的所有喹啉具有相似的生物利用度，则较大的分子无法容纳在仍未知的生物受体内。结果表明碱性拮抗剂分子与拮抗剂-受体复合物中的弱酸性基团相互作用。

  DOI：

  10.1021/jm020374y
• 作为产物：
  描述：

  邻氨基三氟甲苯 在 正丁基锂 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 11.08h， 生成 N-<2-(dimethylamino)ethyl>-2-(4-fluorophenyl)quinolin-4-amine
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationship analysis of 2-(aryl or heteroaryl)quinolin-4-amines, a new class of anti-HIV-1 agents

  摘要：

  Thirty-eight 2-(aryl or heteroaryl)quinolin-4-amines, N,N-disubstituted, N-monosubstituted, and without a substituent at the amino group have been synthesized with use of novel chemistries developed by us recently. Some of these derivatives show anti-HIV-1 activity at a concentration level of 1-mu-M and low cell toxicity in vitro. The most active and least toxic compounds are derivatives of 2-(3-pyridyl)quinoline. The results of the quantitative structure-activity relationship analyses, including several classical, linear regression correlations and a Free-Wilson approach, of de novo model, provide guidelines for the design of new active compounds of this class.

  DOI：

  10.1021/jm00109a031

文献信息

• Amination by lithium alkylamide reagents of ketimines derived from 2-(trifluoromethyl)anilines and methyl halophenyl ketones and their cyclization products 2-(halophenyl)quinolin-4-amines
  作者：Lucjan Strekowski、Lubomir Janda、Steven E Patterson、Johnny Nguyen

  DOI：10.1016/0040-4020(95)01110-2

  日期：1996.2

  title ketimines containing a fluorine atom at position 2 of the phenyl group are efficiently cyclized under mild conditions to N-[2-(dimethylamino)ethyl]-2-(2-fluorophenyl)quinolin-4-amines by the reaction with a lithium reagent derived from N,N-dimethylethylenediamine. The facile regioselective displacement of C2-F in the presence of another fluorine atom at the phenyl group by the same reagent or

  通过与锂的反应，在温和的条件下将在苯基的第2位上含有氟原子的标题酮亚胺有效地环化为N- [2-（二甲基氨基）乙基] -2-（2-氟苯基）喹啉-4-胺。由N，N-二甲基乙二胺衍生的试剂。通过相同的试剂或N-硫代-N在苯基上存在另一个氟原子的情况下C2-F的区域选择性迁移用复杂诱导邻近效应（CIPE）过程解释了较高温度下的'-甲基哌嗪。CIPE工艺可在环化为喹啉之前通过反应性更高的哌嗪试剂对2-氟苯基酮亚胺进行胺化。2-氯苯基衍生物在CIPE辅助胺化反应中的反应性要低得多。
• STREKOWSKI, LUCJAN;MOKROSZ, JERZY L.;HONKAN, VIDYA A.;CZARNY, AGNIESZKA;C+, J. MED. CHEM., 34,(1991) N, C. 1739-1746
  作者：STREKOWSKI, LUCJAN、MOKROSZ, JERZY L.、HONKAN, VIDYA A.、CZARNY, AGNIESZKA、C+

  DOI：——

  日期：——
• Synthesis and quantitative structure-activity relationship analysis of 2-(aryl or heteroaryl)quinolin-4-amines, a new class of anti-HIV-1 agents
  作者：Lucjan Strekowski、Jerzy L. Mokrosz、Vidya A. Honkan、Agnieszka Czarny、Marek T. Cegla、Roman L. Wydra、Steven E. Patterson、Raymond F. Schinazi

  DOI：10.1021/jm00109a031

  日期：1991.5

  Thirty-eight 2-(aryl or heteroaryl)quinolin-4-amines, N,N-disubstituted, N-monosubstituted, and without a substituent at the amino group have been synthesized with use of novel chemistries developed by us recently. Some of these derivatives show anti-HIV-1 activity at a concentration level of 1-mu-M and low cell toxicity in vitro. The most active and least toxic compounds are derivatives of 2-(3-pyridyl)quinoline. The results of the quantitative structure-activity relationship analyses, including several classical, linear regression correlations and a Free-Wilson approach, of de novo model, provide guidelines for the design of new active compounds of this class.
• Synthesis and Activity of Substituted 2-Phenylquinolin-4-amines, Antagonists of Immunostimulatory CpG-Oligodeoxynucleotides
  作者：Lucjan Strekowski、Martial Say、Maged Henary、Patricia Ruiz、Lori Manzel、Donald E. Macfarlane、Andrzej J. Bojarski

  DOI：10.1021/jm020374y

  日期：2003.3.1

  2-phenylquinolines substituted at the phenyl group and C4 of the quinoline were synthesized and analyzed for inhibition of the immunostimulatory effect of oligodeoxynucleotides with a CpG-motif. The Fujita-Ban variant of the classical Free-Wilson analysis gave a highly significant correlation for a series of 48 relatively small molecules demonstrating that (i) the partial contributions of substituents to biological

  合成了在喹啉的苯基和C4处取代的57个2-苯基喹啉，并分析了其对具有CpG基序的寡脱氧核苷酸的免疫刺激作用的抑制作用。经典Free-Wilson分析的Fujita-Ban变体对一系列48个相对较小的分子给出了高度显着的相关性，表明（i）取代基对生物活性的部分贡献（EC（50））是加和的（ii）假设所研究的所有喹啉具有相似的生物利用度，则较大的分子无法容纳在仍未知的生物受体内。结果表明碱性拮抗剂分子与拮抗剂-受体复合物中的弱酸性基团相互作用。