N1,N1-dimethyl-N2-(2-(4-methylphenyl)quinolin-4-yl)ethane-1,2-diamine | 133671-50-8

• 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: N1,N1-dimethyl-N2-(2-(4-methylphenyl)quinolin-4-yl)ethane-1,2-diamine
• 英文别名: N-[2-(dimethylamino)ethyl]-2-(4-methylphenyl)quinolin-4-amine；1,2-Ethanediamine, N,N-dimethyl-N'-(2-(4-methylphenyl)-4-quinolinyl)-；N',N'-dimethyl-N-[2-(4-methylphenyl)quinolin-4-yl]ethane-1,2-diamine
• CAS: 133671-50-8
• 化学式: C₂₀H₂₃N₃
• 分子量: 305.423
• InChiKey: DEUWWPYHIOKTRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  486.5±45.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 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 N1,N1-dimethyl-N2-(2-(4-methylphenyl)quinolin-4-yl)ethane-1,2-diamine
  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

• 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。
• Synthesis and evaluation of graveoline and graveolinine derivatives with potent anti-angiogenesis activities
  作者：Zeng-Yun An、Yi-Yong Yan、Dan Peng、Tian-Miao Ou、Jia-Heng Tan、Shi-Liang Huang、Lin-Kun An、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.ejmech.2010.05.043

  日期：2010.9

  A series of graveoline and graveolinine derivatives were synthesized. The biological results showed that most of graveoline derivatives possessed higher cytotoxicity and better inhibitive effect against the adhesion and migration of human umbilical vein endothelial cell (HUVEC) than graveolinine derivatives. Among these compounds, 8d was the most potent agents that also showed significant anti-angiogenesis activities in chick embryo chorioallantoic membrane (CAM) assay. (C) 2010 Elsevier Masson SAS. All rights reserved.
• 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.