2,4,6-trihydroxy-3,5-di(2'-hydroxybenzyl)-acetophenone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,4,6-trihydroxy-3,5-di(2'-hydroxybenzyl)-acetophenone
• 英文别名: 1-[2,4,6-Trihydroxy-3,5-bis[(2-hydroxyphenyl)methyl]phenyl]ethanone
• 化学式: C₂₂H₂₀O₆
• 分子量: 380.397
• InChiKey: XUIWQLFWGWDTJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  水杨醇 、 2,4,6-三羟基苯乙酮一水合物 在 zinc(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以20%的产率得到2,4,6-trihydroxy-3,5-di(2'-hydroxybenzyl)-acetophenone
  参考文献：
  名称：

  WO2007/56188

  摘要：

  公开号：

文献信息

• Synthesis of Inhibitors of FtsZ
  申请人：Shaw Jared

  公开号：US20090221568A1

  公开（公告）日：2009-09-03

  FtsZ, the bacterial analog of tubulin, is a promising new target for developing new antibiotics. It has been shown that polyphenols inhibit the GTPase activity of FtsZ, thereby inhibiting Z-ring formation during mitosis. The present invention provides novel polyphenols compounds, which can be accessed by the synthesis of dichamametin and 2′″-hydroxy-5″-benzylisouvarinol-B as described herein. These novel compounds are useful in treating infections, particularly infections caused by gram-positive organisms. Methods of preparing the inventive compounds are also provided. The compounds are prepared by the benzylation of pinocembrin or chrysin core structure. Pharmaceutical compositions and method of using the compounds to treat disease are also provided. These compounds may be screened for antimicrobial activity as well as other biological activities such as anti-neoplastic, anti-inflammatory, immunosuppressive, and cytotoxic activity.

  FtsZ是细菌中类似于微管蛋白的有前途的新靶点，可用于开发新型抗生素。已经表明，多酚类物质能够抑制FtsZ的GTP酶活性，从而抑制有丝分裂期间Z环的形成。本发明提供了新型的多酚类化合物，可以通过所述的二氢松香素和2′″-羟基-5″-苄基异乌金醇-B的合成来获得。这些新型化合物在治疗感染，特别是由革兰氏阳性菌引起的感染方面具有用途。还提供了制备本发明化合物的方法。这些化合物通过对松树素或芹菜素核心结构进行苄基化来制备。还提供了制药组合物和使用这些化合物治疗疾病的方法。这些化合物可以筛选抗微生物活性以及其他生物活性，如抗肿瘤、抗炎、免疫抑制和细胞毒性活性。
• Synthesis of Antimicrobial Natural Products Targeting FtsZ:  (±)-Dichamanetin and (±)-2‘ ‘‘-Hydroxy-5‘ ‘-benzylisouvarinol-B
  作者：Sameer Urgaonkar、Henry S. La Pierre、Israel Meir、Henrik Lund、Debabrata RayChaudhuri、Jared T. Shaw

  DOI：10.1021/ol052269z

  日期：2005.12.1

  [GRAPHIC]Two natural products have been synthesized using a ZnCl2-mediated benzylic coupling reaction. Both are potent inhibitors of the GTPase activity of FtsZ, a highly conserved protein that is essential for bacterial cytokinesis.
• [EN] SYNTHESIS OF INHIBITORS OF FTSZ<br/>[FR] SYNTHESE D'INHIBITEURS DE FTFZ
  申请人：HARVARD COLLEGE

  公开号：WO2007056188A1

  公开（公告）日：2007-05-18

  [EN] FtsZ, the bacterial analog of tubulin, is a promising new target for developing new antibiotics. It has been shown that polyphenols inhibit the GTPase activity of FtsZ, thereby inhibiting Z-ring formation during mitosis. The present invention provides novel polyphenols compounds, which can be accessed by the synthesis of dichamametin and 2"'-hydroxy-5"-benzylisouvarinol-B as described herein. These novel compounds are useful in treating infections, particularly infections caused by gram-positive organisms. Methods of preparing the inventive compounds are also provided. The compounds are prepared by the benzylation of pinocembrin or chrysin core structure. Pharmaceutical compositions and method of using the compounds to treat disease are also provided. These compounds may be screened for antimicrobial activity as well as other biological activities such as anti-neoplastic, anti-inflammatory, immunosuppressive, and cytotoxic activity.
  [FR] Le FtsZ, analogue bactérien de la tubuline, est une nouvelle cible prometteuse pour le développement de nouveaux antibiotiques. On a constaté que des polyphénols inhibent l'activité GTPase de FtsZ, inhibant ainsi la formation de cycle Z durant la mitose. L'invention concerne de nouveaux composés polyphénols que l'on peut obtenir par synthèse de dichamamétine et 2" -hydroxy-5"-benzylisouvarinol-B comme spécifié dans la description. Ces nouveaux composés sont utilisés dans le traitement d'infections, en particulier d'infections causées par des organismes Gram positifs. L'invention concerne en outre des procédés de préparation des composés précités. Les composés sont préparés par benzylation d'une structure à noyau de pinocembrine ou de chrysine. L'invention concerne en outre des compositions pharmaceutiques et un procédé d'utilisation des composés pour le traitement de maladies. Ces composés peuvent être criblés quant à leur activité antimicrobienne et d'autres activités biologiques, par exemple, activités antinéoplasiques, anti-inflammatoires, immunosuppressives et cytotoxiques.