4-(tetrahydropyran-2-yloxy)chalcone | 468060-22-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-(tetrahydropyran-2-yloxy)chalcone
• 英文别名: 3-Phenyl-1-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one；(E)-1-[4-(oxan-2-yloxy)phenyl]-3-phenylprop-2-en-1-one
• CAS: 468060-22-2
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: GQHOCRIJRJPRSJ-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-(tetrahydropyran-2-yloxy)chalcone 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 4-[4-Phenyl-6-(propyl-pyridin-2-ylmethyl-amino)-pyridin-2-yl]-phenol
  参考文献：
  名称：

  2-Amino-4,6-diarylpyridines as novel ligands for the estrogen receptor

  摘要：

  We have prepared a novel series of 2-amino-4,6-diarylpyridines that function as ligands of estrogen receptor alpha (ER alpha) and estrogen receptor beta (ER beta). These compounds bind to both ER alpha and ER beta with a modest selectivity for the alpha subtype. The most potent of these analogues, compound 19, has a K-i = 20nM at ER alpha. These molecules represent a novel template for designing potentially useful ligands for the estrogen receptor. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00321-3
• 作为产物：
  描述：

  对羟基苯乙酮 在 sodium hydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-(tetrahydropyran-2-yloxy)chalcone
  参考文献：
  名称：

  抗疟疾烷氧基化和羟基化的查耳酮[校正]：结构-活性关系分析。

  摘要：

  合成在环B上具有2'，3'，4'-三甲氧基，2'，4'-二甲氧基，4'-甲氧基，4'-乙氧基，2'，4'-二羟基和4'-羟基的邻苯二甲酰并在[3H]次黄嘌呤摄取测定中针对恶性疟原虫（K1）进行了体外评估。另一个环A是具有不同亲脂性的给电子或吸电子取代基的喹啉，吡啶，萘或苯环。三甲氧基6和27，二甲氧基7，8，29和甲氧基31类似物具有良好的体外活性（IC（50）<5 microM）。在活性化合物中很好地代表了3-喹啉基环A衍生物。羟基查耳酮的活性低于相应的烷氧基化类似物。在体内评估时，8和208在延长被感染小鼠的寿命方面与氯喹相当。多变量数据分析表明，体外活性主要取决于环B的特性。使用对潜在结构的投影，获得了各种B环查耳酮具有令人满意的预测能力的定量构效关系模型。提出了一个具有良好可预测性的模型，用于19个活动查尔肯。尺寸和疏水性被确定为关键参数。

  DOI：

  10.1021/jm0101747

文献信息

• Synthesis of some pyrazole derivatives and preliminary investigation of their affinity binding to P-glycoprotein
  作者：Fedele Manna、Franco Chimenti、Rossella Fioravanti、Adriana Bolasco、Daniela Secci、Paola Chimenti、Cristiano Ferlini、Giovanni Scambia

  DOI：10.1016/j.bmcl.2005.05.067

  日期：2005.10

  A series of substituted pyrazolines were synthesized and evaluated for their anticancer activity and for their ability to inhibit P-glycoprotein-mediated multidrug resistance by direct binding to a purified protein domain containing an ATP-binding site and a modulator interacting region. Compounds 2a and e have been found to bind to P-glycoprotein with greater affinity.

  合成了一系列取代的吡唑啉，并通过直接结合至包含ATP结合位点和调节剂相互作用区的纯化蛋白结构域，评估了它们的抗癌活性以及抑制P-糖蛋白介导的多药耐药性的能力。已经发现化合物2a和e以更大的亲和力与P-糖蛋白结合。
• Aminopyridine derivatives as estrogen receptor modulators
  申请人：——

  公开号：US20040152688A1

  公开（公告）日：2004-08-05

  Aminopyridine derivatives of the following formula I which exhibit pharmacological activity at estrogen receptors alpha (ER&agr;) and beta (ER&bgr;) are described herein. The described invention also includes compositions and medicaments containing the aminopyridine derivatives as well as processes for the preparation and use of such compounds, compositions and medicaments.

  本文描述了在雌激素受体α（ER&agr;）和β（ER&bgr;）上表现出药理活性的下式I的氨基吡啶衍生物。所述发明还包括含有氨基吡啶衍生物的组合物和药物，以及制备和使用此类化合物、组合物和药物的工艺。
• 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors
  作者：Satoshi Sogawa、Yasunori Nihro、Hiroki Ueda、Akihiro Izumi、Tokutaro Miki、Hitoshi Matsumoto、Toshio Satoh

  DOI：10.1021/jm00076a019

  日期：1993.11

  A novel series of 3,4-dihydroxychalcones was synthesized to evaluate their effects against 5-lipoxygenase and cyclooxygenase. Almost all compounds exhibited potent inhibitory effects on 5-lipoxygenase with antioxidative effects, and some also inhibited cyclooxygenase. The 2',5'-disubstituted 3,4-dihydroxychalcones with hydroxy or alkoxy groups exhibited optimal inhibition of cyclooxygenase. We found that 2',5'-dimethoxy-3,4-dihydroxychalcone (37; HX-0836) inhibited cyclooxygenase to the same degree as flufenamic acid and 6-lipoxygenase, more than quercetin. Finally, these active inhibitors of 5-lipoxygenase inhibited arachidonic acid-induced mouse ear edema more than phenidone.
• US7276523B2
  申请人：——

  公开号：US7276523B2

  公开（公告）日：2007-10-02
• [EN] AMINOPYRIDINE DERIVATIVES AS ESTROGEN RECEPTOR MODULATORS<br/>[FR] DERIVES D'AMINOPYRIDINE UTILISES COMME MODULATEURS DE RECEPTEURS DES OESTROGENES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2002079163A1

  公开（公告）日：2002-10-10

  Aminopyridine derivatives of the following formula I which exhibit pharmacological activity at estrogen receptors alpha (ERα) and beta (ERβ) are described herein. The described invention also includes compositions and medicaments containing the aminopyridine derivatives as well as processes for the preparation and use of such compounds, compositions and medicaments.