2'-hydroxy-4',6'-bis[(2-methoxyethoxy)methoxy]acetophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-hydroxy-4',6'-bis[(2-methoxyethoxy)methoxy]acetophenone
• 英文别名: 2'-hydroxy-4',6'-di-O-MEM-acetophenone；1-{2-hydroxy-4,6-bis[(2-methoxyethoxy)methoxy]phenyl}ethanone；1-[2-hydroxy-4,6-bis(2-methoxyethoxymethoxy)phenyl]ethanone
• 化学式: C₁₆H₂₄O₈
• 分子量: 344.362
• InChiKey: DDVKCFZYPVGURY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-4',6'-bis[(2-methoxyethoxy)methoxy]acetophenone 在 盐酸 、 sodium periodate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 79.0h， 生成 4'-甲基金圣草黄素
  参考文献：
  名称：

  Modulation of human neutrophils' oxidative burst by flavonoids

  摘要：

  Inflammation is a normal response towards tissue injury, but may become deleterious to the organism if uncontrolled. The overproduction of reactive species during the inflammatory process may cause or magnify the damage at inflammatory sites. Flavonoids have been suggested as therapeutic agents to avoid such damage, as these compounds exhibit anti-inflammatory activity, through the modulation of oxidative stress and signalling pathways. Both effects may attenuate neutrophils' activities at inflammatory sites. In this study, we investigated the structure/activity relationship of a series of flavonoids on the oxidative burst of human neutrophils in vitro, as a measure of its anti-inflammatory potential. Neutrophils were stimulated with phorbol-12-myristate-13-acetate, and fluorescence and chemiluminescence techniques were used to evaluate the generation of reactive oxygen species. All the tested flavonoids revealed the ability to modulate the neutrophil's oxidative burst. From the obtained results, the pivotal role of the catechol group in the B-ring was evidenced as well as the minor importance of the hydroxylations in the A-ring, which did not appear to be determinant for the activity, although clearly influencing the lipophilicity of the tested flavonoids. It is also clarified the importance of the methylation in the OH group at the B-ring catechol moiety. In conclusion, the obtained results uncover new possible strategies for the resolution of inflammatory processes, using flavonoids to modulate neutrophil's oxidative burst. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.019
• 作为产物：
  描述：

  2-甲氧基乙氧基甲基氯 、 2,4,6-三羟基苯乙酮一水合物 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到2'-hydroxy-4',6'-bis[(2-methoxyethoxy)methoxy]acetophenone
  参考文献：
  名称：

  [EN] RESORCINOL DERIVATIVES AS HSP90 INHIBITORS
  [FR] DÉRIVÉS DU RÉSORCINOL COMME INHIBITEURS DE LA HSP90

  摘要：

  本发明涉及取代间苯二酚衍生物，这些衍生物抑制热休克蛋白HSP90的活性。因此，本发明的化合物可用于治疗诸如癌症和神经退行性疾病等增殖性疾病。本发明还提供了制备这些化合物的方法、包含它们的药物组合物、治疗疾病的方法以及包含这些化合物的药物组合物。

  公开号：

  WO2010121963A1

文献信息

• RESORCINOL DERIVATIVES AS HSP90 INHIBITORS
  申请人：Brasca Maria Gabriella

  公开号：US20120046266A1

  公开（公告）日：2012-02-23

  The present invention relates to substituted resorcinol derivatives which inhibit the activity of Heat Shock Protein HSP90. The compounds of the invention are therefore useful in treating proliferative diseases such as cancer and neurodegenerative diseases. The present invention also provides processes for preparing these compounds, pharmaceutical compositions comprising them, methods of treating diseases and the pharmaceutical compositions comprising these compounds.

  本发明涉及替代苯醌衍生物，其抑制热休克蛋白HSP90的活性。因此，本发明的化合物在治疗增殖性疾病如癌症和神经退行性疾病方面有用。本发明还提供制备这些化合物的方法，包括它们的药物组合物，治疗疾病的方法以及包含这些化合物的药物组合物。
• Resorcinol derivatives as HSP90 inhibitors
  申请人：Brasca Maria Gabriella

  公开号：US08993556B2

  公开（公告）日：2015-03-31

  The present invention relates to substituted resorcinol derivatives which inhibit the activity of Heat Shock Protein HSP90. The compounds of the invention are therefore useful in treating proliferative diseases such as cancer and neurodegenerative diseases. The present invention also provides processes for preparing these compounds, pharmaceutical compositions comprising them, methods of treating diseases and the pharmaceutical compositions comprising these compounds.

  本发明涉及替代苯酚衍生物，其抑制热休克蛋白HSP90的活性。该发明的化合物因此可用于治疗增殖性疾病，如癌症和神经退行性疾病。本发明还提供了制备这些化合物的方法，包括它们的制药组合物，治疗疾病的方法以及包括这些化合物的制药组合物。
• Synthesis and biological activity of 4-alkoxy chalcones: potential hydrophobic modulators of p-glycoprotein-mediated multidrug resistance
  作者：Frédéric Bois、Ahcène Boumendjel、Anne-Marie Mariotte、Gwenaëlle Conseil、Attilio Di Petro

  DOI：10.1016/s0968-0896(99)00218-7

  日期：1999.12

  A series of 4-alkoxy-2',4',6'-trihydroxychalcones have been synthesized and evaluated for their ability to inhibit P-glycoprotein-mediated multidrug resistance (MDR) by direct binding to a purified protein domain containing an ATP-binding site and a modulator-interacting region. The introduction of hydrophobic alkoxy groups at position 4 led to much more active compounds as compared to the parent chalcone. The binding affinity increased as a function of the chain length, up to the octyloxy derivative for which a K-D of 20 nM was obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Halogenated Chalcones with High-Affinity Binding to P-Glycoprotein:  Potential Modulators of Multidrug Resistance
  作者：Frédéric Bois、Chantal Beney、Ahcène Boumendjel、Anne-Marie Mariotte、Gwenaëlle Conseil、Attilio Di Pietro

  DOI：10.1021/jm9810194

  日期：1998.10.1

  Previous studies have shown that flavonoids are modulators of the transmembrane P-glycoprotein (P-gp) which mediates cell multidrug resistance. Some structural elements have been identified which seem to contribute to these compounds' activity. In the present study, a series of halogenated chalcones was prepared to further explore the structural requirements for the P-gp modulation. Four halogenated chalcones have been synthesized and evaluated as potential modulators of P-gp-mediated multidrug resistance of cancer cells by in vitro assays using a purified recombinant domain of the transporter containing the modulator binding site. Halogenated chalcones exhibited high-affinity binding, the 2',4', 6'-trihydroxy-4-iodochalcone behaving as the most potent compound with a K-D value in the nanomolar range.
• US8993556B2
  申请人：——

  公开号：US8993556B2

  公开（公告）日：2015-03-31