α-bromo-phenethyl 2,4-dichlorophenyl ketone

• 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: α-bromo-phenethyl 2,4-dichlorophenyl ketone
• 英文别名: 2-Bromo-1-(2,4-dichlorophenyl)-3-phenylpropan-1-one
• 化学式: C₁₅H₁₁BrCl₂O
• 分子量: 358.062
• InChiKey: SLIQQRNJSXDOLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-bromo-phenethyl 2,4-dichlorophenyl ketone 在 sodium tetrahydroborate 、 sodium acetate 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 5-benzyl-4-(2,4-dichlorophenyl)-N-(4-methoxybenzyl)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
• 作为产物：
  描述：

  2,4-二氯苯乙酮 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 α-bromo-phenethyl 2,4-dichlorophenyl ketone
  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

• Thiazole derivatives and pharmaceutical compositions containing them
  申请人：Synthelabo

  公开号：US04349557A1

  公开（公告）日：1982-09-14

  Thiazole derivatives of the general formula: ##STR1## wherein n represents 1 or 2 and each of X and Y independently of one another represents one or more substituents selected from hydrogen and halogen atoms, the trifluoromethyl radical and straight- or branched-chain alkyl and alkoxy radicals of 1 to 4 carbon atoms, are new therapeutically useful compounds, especially of interest in the treatment of depression.

  通式为：##STR1##其中n代表1或2，X和Y分别独立地代表氢原子和卤原子、三氟甲基基团以及1到4个碳原子的直链或支链烷基和烷氧基取代基的一种或多种取代基。这些新的治疗上有用的化合物，特别在抑郁症治疗方面具有重要意义。
• US4349557A
  申请人：——

  公开号：US4349557A

  公开（公告）日：1982-09-14
• 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.