5-hydroxy-2-(phenoxymethyl)-4H-chromen-4-one | 1579990-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-hydroxy-2-(phenoxymethyl)-4H-chromen-4-one
• 英文别名: 5-Hydroxy-2-(phenoxymethyl)chromen-4-one；5-hydroxy-2-(phenoxymethyl)chromen-4-one
• CAS: 1579990-05-8
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: OPVBDJVHHCLNCN-UHFFFAOYSA-N

物化性质

• 沸点：
  453.8±45.0 °C(predicted)
• 密度：
  1.321±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯氧乙酸 在 盐酸 、 sodium hydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.17h， 生成 5-hydroxy-2-(phenoxymethyl)-4H-chromen-4-one
  参考文献：
  名称：

  5-羟基-2-（2-苯乙基）色酮（5-HPEC）的合成，表征及其与非氮5-HT 2B配体的类似物

  摘要：

  神经递质5-羟色胺（5-HT）参与多种生理功能通常归因于与之相互作用的受体的多样性。靶向血清素2B（5-HT 2B）的配体因其潜在的帮助理解5-HT 2B在偏头痛，药物滥用，神经退行性疾病和肠易激综合症中的作用而引起了新的兴趣。迄今为止，大多数靶向5-HT 2B的配体都是含氮化合物。天然产物5-羟基-2-（2-苯基乙基）色酮（5-HPEC，5）先前已显示出可作为5-HT 2B受体的非氮拮抗剂（p K i= 5.6）。该报告描述了在5-HT 2B受体上带有2-（2-苯乙基）色酮骨架的天然和合成化合物的结构-活性关系研究的进一步进展。测试了新合成的化合物（10μM）对每种5-HT 2受体的抑制活性。在该测定之后，然后在5-HT 2B处评估最有希望的化合物的结合亲和力和拮抗作用。在所有类似物中，出现了5-羟基-2-（2-苯基丙基）苯甲酮（5-HPPC，22h）作为一种新的先导化合物，与5-HPEC相比，亲和力提高了10倍（p

  DOI：

  10.1021/acs.jnatprod.5b00118

文献信息

• [EN] 2-SUBSTITUTED-5-HYDROXY-4H-CHROMEN-4-ONES AS NOVEL LIGANDS FOR THE SEROTONIN RECEPTOR 2B (5-HT2B)<br/>[FR] 5-HYDROXY-4 H-CHROMÈNE-4-ONES SUBSTITUÉS EN 2 COMME NOUVEAUX LIGANDS POUR LE RÉCEPTEUR DE LA SÉROTONINE 2B (5-HT2B)
  申请人：UNIV VIRGINIA COMMONWEALTH

  公开号：WO2015116460A1

  公开（公告）日：2015-08-06

  A family of compounds which function as selective ligands for the serotonin receptor 2B (5-HT2B) is identified. Some of the compounds are synthetic non-natural ligands which have a relatively strong interaction with 5-HT2B compared to naturally occurring compounds (some of which are identified for the first time herein as ligands for 5-HT2B). Because the compounds, both naturally occurring and synthetically produced, function as ligands for 5-HT2B they will have application in, for example, the treatment and/or prevention of nervous system disorders such as Alzheimer's disease.

  已鉴定出一类化合物家族，其作为选择性血清素受体2B（5-HT2B）的配体。其中一些化合物是合成的非天然配体，与天然存在的化合物相比，它们与5-HT2B有相对较强的相互作用（其中一些在此处首次被确认为5-HT2B的配体）。由于这些化合物，无论是天然存在的还是合成的，都作为5-HT2B的配体，它们将在治疗和/或预防神经系统疾病如阿尔茨海默病等方面发挥作用。
• 5-Hydroxy-2-(2-phenylethyl)chromone (5-HPEC): A novel non-nitrogenous ligand for 5-HT2B receptor
  作者：Dwight A. Williams、Saheem A. Zaidi、Yan Zhang

  DOI：10.1016/j.bmcl.2014.02.029

  日期：2014.3

  Chromones are a class of natural products found in almost every known terrestrial plant with over 4000 naturally occurring derivatives having been isolated and structurally elucidated. Recently, 5-hydroxy-2-(2-phenylethyl) chromone (5-HPEC), isolated from Imperata cylindrical, showed neuroprotective activity against glutamate induced excitotoxicity in primary cultures of rat cortical cells. In comparison to other naturally occurring neuroprotective chromones, 5-HPEC contains fewer hydroxyl groups. Here we report our most recent characterization on this interesting natural product against a number of CNS receptors for the purpose to identify the potential molecular targets that may be related to its biological activity. Based on our studies, including radiobinding assays, calcium flux functional assays and molecular modeling studies, 5-HPEC may represent a type of novel nonnitrogenous ligands to the 5-HT2B receptor. Published by Elsevier Ltd.
• 2-SUBSTITUTED-5-HYDROXY-4H-CHROMEN-4-ONES AS NOVEL LIGANDS FOR THE SEROTONIN RECEPTOR 2B (5-HT2B)
  申请人：VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：US20170029399A1

  公开（公告）日：2017-02-02

  A family of compounds which function as selective ligands for the serotonin receptor 2B (5-HT 2B ) is identified. Some of the compounds are synthetic non-natural ligands which have a relatively strong interaction with 5-HT2B compared to naturally occurring compounds (some of which are identified for the first time herein as ligands for 5-HT 2B ). Because the compounds, both naturally occurring and synthetically produced, function as ligands for 5-HT 2B they will have application in, for example, the treatment and/or prevention of nervous system disorders such as Alzheimer's disease.
• US9884836B2
  申请人：——

  公开号：US9884836B2

  公开（公告）日：2018-02-06
• Synthesis and Characterization of 5-Hydroxy-2-(2-phenylethyl)chromone (5-HPEC) and Its Analogues as Non-nitrogenous 5-HT_2B Ligands
  作者：Dwight A. Williams、Saheem A. Zaidi、Yan Zhang

  DOI：10.1021/acs.jnatprod.5b00118

  日期：2015.8.28

  nitrogen-containing compounds. The natural product 5-hydroxy-2-(2-phenylethyl)chromone (5-HPEC, 5) has been shown previously to act as a non-nitrogenous antagonist for the 5-HT2B receptor (pKi = 5.6). This report describes further progress on the study of the structure–activity relationship of both naturally occurring and synthetic compounds bearing the 2-(2-phenylethyl)chromone scaffold at the 5-HT2B receptor. The

  神经递质5-羟色胺（5-HT）参与多种生理功能通常归因于与之相互作用的受体的多样性。靶向血清素2B（5-HT 2B）的配体因其潜在的帮助理解5-HT 2B在偏头痛，药物滥用，神经退行性疾病和肠易激综合症中的作用而引起了新的兴趣。迄今为止，大多数靶向5-HT 2B的配体都是含氮化合物。天然产物5-羟基-2-（2-苯基乙基）色酮（5-HPEC，5）先前已显示出可作为5-HT 2B受体的非氮拮抗剂（p K i= 5.6）。该报告描述了在5-HT 2B受体上带有2-（2-苯乙基）色酮骨架的天然和合成化合物的结构-活性关系研究的进一步进展。测试了新合成的化合物（10μM）对每种5-HT 2受体的抑制活性。在该测定之后，然后在5-HT 2B处评估最有希望的化合物的结合亲和力和拮抗作用。在所有类似物中，出现了5-羟基-2-（2-苯基丙基）苯甲酮（5-HPPC，22h）作为一种新的先导化合物，与5-HPEC相比，亲和力提高了10倍（p