3'-(1,3-Dioxolan-2-yl)[1,1'-biphenyl]-2-carbaldehyde | 893737-24-1

• 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]-2-carbaldehyde
• 英文别名: 2-[3-(1,3-dioxolan-2-yl)phenyl]benzaldehyde
• CAS: 893737-24-1
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: TVMPCRZGPKIQIO-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]-2-carbaldehyde 在 lithium aluminium tetrahydride 、 18-冠醚-6 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 三溴化硼 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， -78.0~20.0 ℃ 、400.01 kPa 条件下， 反应 110.0h， 生成 Pentacyclo[21.2.2.116,20.02,7.010,15]octacosa-1(25),2(7),3,5,10,12,14,16,18,20(28),23,26-dodecaene-5,25-diol
  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
• 作为产物：
  描述：

  2-(3-溴苯基)-1,3-二氧烷 、 2-甲酰基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 14.0h， 以73%的产率得到3'-(1,3-Dioxolan-2-yl)[1,1'-biphenyl]-2-carbaldehyde
  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

文献信息

• N-(2-arylethyl) benzylamines as antagonists of the 5-ht6 receptor
  申请人：Chen Zhaogen

  公开号：US20060009511A9

  公开（公告）日：2006-01-12

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT 6 receptor.

  本发明提供了式(I)的化合物，它们是5-HT6受体的拮抗剂。
• N-(2-ARYLETHYL)BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR
  申请人：Chen Zhaogen

  公开号：US20070099909A1

  公开（公告）日：2007-05-03

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT 6 receptor.

  本发明提供了公式（I）的化合物，它们是5-HT6受体的拮抗剂。
• N-(2-ARYLETHYL) BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR
  申请人：ELI LILLY AND COMPANY

  公开号：EP1859798B1

  公开（公告）日：2015-12-30
• US7157488B2
  申请人：——

  公开号：US7157488B2

  公开（公告）日：2007-01-02
• US8044090B2
  申请人：——

  公开号：US8044090B2

  公开（公告）日：2011-10-25