2-Bromo-3-(2-methoxyphenyl)-1-phenylpropan-1-one | 1446018-69-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-Bromo-3-(2-methoxyphenyl)-1-phenylpropan-1-one
• CAS: 1446018-69-4
• 化学式: C₁₆H₁₅BrO₂
• 分子量: 319.198
• InChiKey: VDNGLLBPYRVILF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Bromo-3-(2-methoxyphenyl)-1-phenylpropan-1-one 在 sodium tetrahydroborate 、 sodium acetate 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 5-(2-methoxybenzyl)-N-(4-methoxybenzyl)-4-phenylthiazol-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
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 aluminum (III) chloride 、 palladium on activated charcoal 、 氢气 、 溴 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 6.17h， 生成 2-Bromo-3-(2-methoxyphenyl)-1-phenylpropan-1-one
  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 as HIV-1 NNRTIs effective on both wild-type and mutant HIV-1 reverse transcriptase: Optimization of the substitution of positions 4 and 5
  作者：Zhongliang Xu、Jiamei Guo、Ying Yang、Mengdi Zhang、Mingyu Ba、Zhenzhong Li、Yingli Cao、Ricai He、Miao Yu、Hua Zhou、Xiaoxi Li、Xiaoshan Huang、Ying Guo、Changbin Guo

  DOI：10.1016/j.ejmech.2016.07.047

  日期：2016.11

  In our previous work, novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were synthesized, and their activities were evaluated against HIV-1 reverse transcriptase. Some interesting results were obtained, which led us to a new discovery regarding these TST5. In the present study, 21 new 2,4,5-trisubstituted thiazole derivatives were rationally designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) in accordance with our previous study. Among the synthesized target compounds, compounds 14, 16, 17, and 19 showed more potent inhibitory activities against HIV-1 with an IC50 value of 0.010 mu M. Compounds 4, 9, 10, 11, 13 and 16 were further tested on nine NNRTI-sresistant HIV-1 strains, and all of these compounds exhibited inhibitory effects. A molecular docking study was conducted, and the results showed a consistent and stable binding mode for the typical compounds. These results have provided deeper insights and SAR of these types of NNRTIs. (C) 2016 Elsevier Masson SAS. All rights reserved.