(2′,4-dimethoxy-(4′-(methoxycarbonyl)[1,1′-biphenyl]-2-yl)methyl)triphenylphosphonium bromide

• 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: (2′,4-dimethoxy-(4′-(methoxycarbonyl)[1,1′-biphenyl]-2-yl)methyl)triphenylphosphonium bromide
• 英文别名: ((2',4-dimethoxy-4'-(methoxycarbonyl)-[1,1'-biphenyl]-2-yl)methyl)triphenylphosphonium bromide；[5-methoxy-2-(2-methoxy-4-methoxycarbonylphenyl)phenyl]methyltriphenyl phosphonium bromide；{5-methoxy-2-[2-methoxy-4-(methoxycarbonyl)phenyl]benzyl}-triphenylphosphonium bromide；{5-methoxy-2-[2-methoxy-4-(methoxycarbonyl)phenyl]benzyl}triphenylphosphonium bromide；5-methoxy-2-(2-methoxy-4-methoxycarbonylphenyl)phenylmethyltriphenyl-phosphonium bromide；[5-Methoxy-2-(2-methoxy-4-methoxycarbonylphenyl)phenyl]methyl-triphenylphosphanium;bromide
• 化学式: Br*C₃₅H₃₂O₄P
• 分子量: 627.514
• InChiKey: GFZXKCAMABCHCS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2′,4-dimethoxy-(4′-(methoxycarbonyl)[1,1′-biphenyl]-2-yl)methyl)triphenylphosphonium bromide 在 palladium on activated charcoal 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 氢溴酸 、 氢气 、 sodium methylate 、 potassium carbonate 、 氯化铵 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 乙酸乙酯 、 甲苯 为溶剂， 20.0~100.0 ℃ 、500.0 kPa 条件下， 反应 95.0h， 生成 1,2,13,14-tetrahydro-9,17,22-trimethoxy-3,6:5,18-dietheno-8,12-metheno-12H-7-benzooxacycloeicosine
  参考文献：
  名称：

  Syntheses of Cyclic Bisbibenzyl Systems

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<877::aid-ejoc877>3.0.co;2-s
• 作为产物：
  描述：

  香草酸甲酯 在 吡啶 、 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.5h， 生成 (2′,4-dimethoxy-(4′-(methoxycarbonyl)[1,1′-biphenyl]-2-yl)methyl)triphenylphosphonium bromide
  参考文献：
  名称：

  Syntheses of Cyclic Bisbibenzyl Systems

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<877::aid-ejoc877>3.0.co;2-s

文献信息

• Syntheses of Chlorinated Bisbibenzyls from Bryophytes
  作者：Andreas Speicher、Jürgen Kolz、Rufino Paulino Sambanje

  DOI：10.1055/s-2002-35629

  日期：——

  Chlorinated bisbibenzyls of the isoplagiochin type detected in different bryophyte species were synthesized by an efficient and flexible unit construction system making extensive use of Suzuki and Wittig protocols.

  在检测到的不同苔藓植物中的异型二苯并双芴类的氯化物，是通过一种高效的、灵活的单元构建系统合成的，该系统广泛采用了铃木和维蒂希方案。
• Co-existence of α-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development
  作者：Kosuke Dodo、Atsushi Aoyama、Tomomi Noguchi-Yachide、Makoto Makishima、Hiroyuki Miyachi、Yuichi Hashimoto

  DOI：10.1016/j.bmc.2008.02.078

  日期：2008.4

  investigate the alpha-glucosidase-inhibitory activity of typical LXR ligands and the LXR-modulating activity of typical alpha-glucosidase inhibitors. Although there were some exceptions, co-existence of LXR-regulatory and alpha-glucosidase-inhibitory activities seemed to be rather general among the examined compounds. The LXR ligands were found to be non-competitive alpha-glucosidase inhibitors, suggesting that

  最初被报道为氧固醇激活的核受体的肝X受体（LXR）最近被发现将葡萄糖识别为生理配体。在此基础上，我们已经开发了基于源自沙利度胺的α-葡萄糖苷酶抑制剂的新型LXR拮抗剂。在这里，为了阐明α-葡萄糖苷酶抑制与LXR调节之间的关系，我们研究了典型的LXR配体的α-葡萄糖苷酶抑制活性和典型的α-葡萄糖苷酶抑制剂的LXR调节活性。尽管有一些例外，但在所研究的化合物中，LXR调节和α-葡萄糖苷酶抑制活性的共存似乎相当普遍。LXR配体被发现是非竞争性的α-葡萄糖苷酶抑制剂，这表明可能有可能分开这两种活性。为了检验这一想法，我们集中研究了蓖麻毒素C（一种自然存在的LXR配体），在这里我们发现它也是有效的α-葡萄糖苷酶抑制剂。riccardin C的结构发展提供了缺乏α-葡萄糖苷酶抑制活性的新型LXR拮抗剂19c和19f，以及LXRalpha选择性拮抗剂22。
• Anti-MRSA activity of isoplagiochin-type macrocyclic bis(bibenzyl)s is mediated through cell membrane damage
  作者：Kenji Onoda、Hiromi Sawada、Daichi Morita、Kana Fujii、Hiroaki Tokiwa、Teruo Kuroda、Hiroyuki Miyachi

  DOI：10.1016/j.bmc.2015.04.047

  日期：2015.7

  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.
• Structure–anti-MRSA activity relationship of macrocyclic bis(bibenzyl) derivatives
  作者：Hiromi Sawada、Kenji Onoda、Daichi Morita、Erika Ishitsubo、Kenji Matsuno、Hiroaki Tokiwa、Teruo Kuroda、Hiroyuki Miyachi

  DOI：10.1016/j.bmcl.2013.10.069

  日期：2013.12

  We synthesized a series of macrocyclic bis(bibenzyl) derivatives, including riccardin-, isoplagiochin- and marchantin-class structures, and evaluated their antibacterial activity towards methicillin-resistant Staphylococcus aureus (anti-MRSA activity). The structure-activity relationships and the results of molecular dynamics simulations indicated that bis(bibenzyl)s with potent anti-MRSA activity commonly have a 4-hydroxyl group at the D-benzene ring and a 2-hydroxyl group at the C-benzene ring in the hydrophilic part of the molecule, and an unsubstituted phenoxyphenyl group in the hydrophobic part of the molecule containing the A-B-benzene rings. Pharmacological characterization of the bis(bibenzyl) derivatives and 2-phenoxyphenol fragment 25, previously proposed as the minimum structure of riccardin C 1 for anti-MRSA activity, indicated that they have different action mechanisms: the bis(bibenzyl) s are bactericidal, while 25 is bacteriostatic, showing only weak bactericidal activity. (C) 2013 Elsevier Ltd. All rights reserved.
• Riccardin C derivatives as anti-MRSA agents: Structure–activity relationship of a series of hydroxylated bis(bibenzyl)s
  作者：Hiromi Sawada、Miki Okazaki、Daichi Morita、Teruo Kuroda、Kenji Matsuno、Yuichi Hashimoto、Hiroyuki Miyachi

  DOI：10.1016/j.bmcl.2012.10.052

  日期：2012.12

  Members of a series of macrocyclic bis(bibenzyl) riccardin-class derivatives were found to exhibit antibacterial activity towards methicillin-resistant Staphylococcus aureus (anti-MRSA activity). Structure-activity relationship (SAR) studies were conducted, focusing on the number and position of the hydroxyl groups. The minimum essential structure for anti-MRSA activity was also investigated. (C) 2012 Elsevier Ltd. All rights reserved.