(E)-N-(4-(3-(3,4-dihydroxyphenyl)acryloyl)phenyl)-1-adamantylamide | 1273524-44-9

• 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: (E)-N-(4-(3-(3,4-dihydroxyphenyl)acryloyl)phenyl)-1-adamantylamide
• 英文别名: FtsZ-IN-9；N-[4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]phenyl]adamantane-1-carboxamide
• CAS: 1273524-44-9
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: IAEGEBQBPTWKEV-LREOWRDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氨基苯乙酮 在 甲烷磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.08h， 生成 (E)-N-(4-(3-(3,4-dihydroxyphenyl)acryloyl)phenyl)-1-adamantylamide
  参考文献：
  名称：

  Design and synthesis of caffeoyl-anilides as portmanteau inhibitors of HIV-1 integrase and CCR5

  摘要：

  Designing multi-functional ligands is a recent strategy by which multiple targets can be inhibited by a single entity. A series of caffeoyl-anilide compounds based on structures of various integrase and CCR5 inhibitors have been designed and synthesized as anti-HIV agents in the present study. Most of the compounds exhibited potent anti-HIV activity at micromolar concentration in CEM-GFP CD4+ T cells infected with HIV-1NL4.3 virus. Compound 14 showed a lower EC50 and better TI as compared to AZT. Mechanism based studies suggest that these compounds inhibit either one or in some cases, both the targets. The experimental data and the docking results showed that these compounds are potential inhibitors for both HIV-1 IN and CCR5. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.031

文献信息

• An adamantyl-caffeoyl-anilide exhibits broad-spectrum antibacterial activity by inhibiting FtsZ assembly and Z-ring formation
  作者：Prajakta Bhondwe、Neha Sengar、Hardik S. Bodiwala、Inder Pal Singh、Dulal Panda

  DOI：10.1016/j.ijbiomac.2024.129255

  日期：2024.2

  MsFtsZ and produces conformational changes in FtsZ. The docking analysis indicated that the compound binds at the interdomain cleft of MsFtsZ. Further, it caused delocalization of the Z-ring in Mycobacterium smegmatis and Bacillus subtilis without affecting DNA segregation. Notably, compound 11 did not inhibit tubulin polymerization, the eukaryotic homolog of FtsZ, suggesting its specificity on bacteria

  由于广泛使用，一些有害细菌已经对传统抗生素产生了耐药性。 FtsZ 是一种主要的细菌细胞分裂蛋白，被认为是对抗耐药性的重要药物靶点。我们鉴定出咖啡酰苯胺衍生物 ( E )-N-(4-(3-(3,4-二羟基苯基)丙烯酰基)苯基)-1-金刚酰胺（化合物11 ）作为针对 FtsZ 的新型抗菌剂。化合物11引起耻垢分枝杆菌、枯草芽孢杆菌和大肠杆菌细胞的细胞伸长，表明它抑制细胞分裂。化合物11抑制耻垢分枝杆菌FtsZ（ Ms FtsZ）的组装，在体外形成短而细的丝。有趣的是，该化合物提高了Ms FtsZ 的 GTP 水解速率。化合物11还阻碍结核分枝杆菌FtsZ 的组装。荧光和吸收光谱分析表明化合物11与Ms FtsZ结合并在FtsZ中产生构象变化。对接分析表明该化合物结合在Ms FtsZ 的域间裂口处。此外，它导致耻垢分枝杆菌和枯草芽孢杆菌中的Z环离域，但不影响 DNA 分离。值得注意的是，化合物11不会抑制微管蛋白聚合（FtsZ
• Design and synthesis of caffeoyl-anilides as portmanteau inhibitors of HIV-1 integrase and CCR5
  作者：Hardik S. Bodiwala、Sudeep Sabde、Pawan Gupta、Ruchira Mukherjee、Rajender Kumar、Prabha Garg、Kamlesh Kumar Bhutani、Debashis Mitra、Inder Pal Singh

  DOI：10.1016/j.bmc.2010.12.031

  日期：2011.2

  Designing multi-functional ligands is a recent strategy by which multiple targets can be inhibited by a single entity. A series of caffeoyl-anilide compounds based on structures of various integrase and CCR5 inhibitors have been designed and synthesized as anti-HIV agents in the present study. Most of the compounds exhibited potent anti-HIV activity at micromolar concentration in CEM-GFP CD4+ T cells infected with HIV-1NL4.3 virus. Compound 14 showed a lower EC50 and better TI as compared to AZT. Mechanism based studies suggest that these compounds inhibit either one or in some cases, both the targets. The experimental data and the docking results showed that these compounds are potential inhibitors for both HIV-1 IN and CCR5. (C) 2010 Elsevier Ltd. All rights reserved.