5-benzyl-N,N-diethyl-4-(4-methoxyphenyl)thiazol-2-amine | 1446017-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-benzyl-N,N-diethyl-4-(4-methoxyphenyl)thiazol-2-amine
• 英文别名: 5-benzyl-N,N-diethyl-4-(4-methoxyphenyl)-1,3-thiazol-2-amine
• CAS: 1446017-90-8
• 化学式: C₂₁H₂₄N₂OS
• 分子量: 352.5
• InChiKey: BPMGWXYHNZEHAS-UHFFFAOYSA-N

物化性质

• 熔点：
  83.2-83.6 °C
• 沸点：
  498.3±55.0 °C(predicted)
• 密度：
  1.130±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-benzyl-N,N-diethyl-4-(4-methoxyphenyl)thiazol-2-amine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以18.8%的产率得到4-(5-benzyl-2-(diethylamino)thiazol-4-yl)phenol
  参考文献：
  名称：

  2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase

  摘要：

  Novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Among the thirty-eight synthesized target compounds, thirty TSTs showed potent inhibition against HIV-1 replication in wild type HIV-1 at submicromolar concentrations (from 0.046 to 9.59 mu M). Compounds 21, 23 and 24 were also tested on seven NNRTI-resistant HIV-1 strains, and all exhibited inhibitory effects with fold changes in IC50 ranging from 2.6 to 111, which were better than those of nevirapine (15.6-fold-371-fold). Docking simulations of compound 24 revealed a reasonable mechanism for the binding mode, and three-dimensional quantitative structure activity relationship (3-DQSAR) studies on this novel series of TST further elucidated the structure-activity relationship (SAR). The results suggested the great potential of TSTs as a novel class of NNRTIs with antiviral efficacy and a good resistance profile. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.072
• 作为产物：
  描述：

  1-(4-甲氧基苯基)-3-苯基-丙-1-酮 在 aluminum (III) chloride 、 lithium hydroxide monohydrate 、 溴 、 sodium acetate 、 亚硝酸异戊酯 作用下， 以 乙醇 、 氯仿 、 水 、 乙腈 为溶剂， 反应 21.33h， 生成 5-benzyl-N,N-diethyl-4-(4-methoxyphenyl)thiazol-2-amine
  参考文献：
  名称：

  2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase

  摘要：

  Novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Among the thirty-eight synthesized target compounds, thirty TSTs showed potent inhibition against HIV-1 replication in wild type HIV-1 at submicromolar concentrations (from 0.046 to 9.59 mu M). Compounds 21, 23 and 24 were also tested on seven NNRTI-resistant HIV-1 strains, and all exhibited inhibitory effects with fold changes in IC50 ranging from 2.6 to 111, which were better than those of nevirapine (15.6-fold-371-fold). Docking simulations of compound 24 revealed a reasonable mechanism for the binding mode, and three-dimensional quantitative structure activity relationship (3-DQSAR) studies on this novel series of TST further elucidated the structure-activity relationship (SAR). The results suggested the great potential of TSTs as a novel class of NNRTIs with antiviral efficacy and a good resistance profile. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.072