4-((5-benzyl-4-(4-methoxyphenyl)thiazol-2-ylamino)methyl)benzonitrile | 1446017-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-((5-benzyl-4-(4-methoxyphenyl)thiazol-2-ylamino)methyl)benzonitrile
• 英文别名: 4-[[[5-Benzyl-4-(4-methoxyphenyl)thiazol-2-yl]amino]methyl]benzonitrile；4-[[[5-benzyl-4-(4-methoxyphenyl)-1,3-thiazol-2-yl]amino]methyl]benzonitrile
• CAS: 1446017-86-2
• 化学式: C₂₅H₂₁N₃OS
• 分子量: 411.527
• InChiKey: IBTXUDKAERJZBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  86.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-甲氧基苯基)-3-苯基-丙-1-酮 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 溴 、 sodium acetate 、 对甲苯磺酸 作用下， 以 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 6.0h， 生成 4-((5-benzyl-4-(4-methoxyphenyl)thiazol-2-ylamino)methyl)benzonitrile
  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

文献信息

• 2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase
  作者：Zhongliang Xu、Mingyu Ba、Hua Zhou、Yingli Cao、Chaojun Tang、Ying Yang、Ricai He、Yu Liang、Xuemei Zhang、Zhenzhong Li、Lihong Zhu、Ying Guo、Changbin Guo

  DOI：10.1016/j.ejmech.2014.07.072

  日期：2014.10

  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.