3'-(1,3-dioxolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde | 893737-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3'-(1,3-dioxolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde
• 英文别名: 3'-(1,3-Dioxolan-2-yl)[1,1'-biphenyl]-4-carbaldehyde；4-[3-(1,3-dioxolan-2-yl)phenyl]benzaldehyde
• CAS: 893737-18-3
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: DOUMAXMUAJUAJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3'-(1,3-dioxolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde 在 18-冠醚-6 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 4.0h， 生成 methyl 2'-(2-(3'-(1,3-dioxolan-2-yl)-[1,1'-biphenyl]-4-yl)ethyl)-2,4'-dimethoxy-[1,1'-biphenyl]-4-carboxylate
  参考文献：
  名称：

  Anti-MRSA activity of isoplagiochin-type macrocyclic bis(bibenzyl)s is mediated through cell membrane damage

  摘要：

  We synthesized three geometrical isomers of a macrocyclic bis(bibenzyl) based on isoplagiochin, a natural product isolated from bryophytes, and evaluated their antibacterial activity towards methicillin-resistant Staphylococcus aureus (anti-MRSA activity). The isomer containing a 1,4-linked ring (5) showed only weak activity, whereas the isomers containing a 1,3-linked (6) or 1,2-linked (7) C ring showed potent anti-MRSA activity. Molecular dynamics calculations indicated that these differences are probably due to differences in the conformational flexibility of the macrocyclic ring; the active compounds 6 and 7 were more rigid than 5.In order to understand the action mechanism of anti-MRSA activity, we investigated the cellular flux of a fluorescent DNA-binder, ethidium bromide (EtBr), in the presence and absence of these macrocycles. The active compound 6 increased the levels of EtBr inflow and outflow in S. aureus cells, as did our potent anti-MRSA riccardin derivative (4), indicating that these compounds increased the permeability of the cytoplasmic membrane. Inactive 5 had no effect on EtBr inflow or outflow. Furthermore, compound 6 abrogated the normal intracellular concentration gradients of Na+ and K+ in S. aureus cells, increasing the intracellular Na+ concentration and decreasing the K+ concentration, while 5 had no such effect. These results indicate that anti-MRSA-active macrocyclic bis(bibenzyl) derivatives directly damage the gram-positive bacterial membrane, resulting in increased permeability. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.047