(E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one | 51589-67-4

• 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: (E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-methoxyphenyl)-propenone；4-methoxylonchocarpin；(E)-1-(5-hydroxy-2,2-dimethylchromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 51589-67-4
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: XEVCTBKORYCFCZ-UXBLZVDNSA-N

物化性质

• 沸点：
  535.2±50.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one 在 盐酸 、 thallium(III) nitrate trihydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 3-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-benzo[1,2-b:3,4-b']dipyran
  参考文献：
  名称：

  Synthesis and biological evaluation of pyranoisoflavone derivatives as anti-inflammatory agents

  摘要：

  In this paper, barbigerone (1a) and its twenty-seven related structural analogues were synthesized via complementary synthetic routes and their anti-inflammatory effects on the expression of TNF-α in LPS-stimulated splenocytes were evaluated. Among these compounds, 1a, 1d, 1f and 1g were found to remarkably inhibit TNF-α production. Furthermore, 1g showed the most potent and dose-dependent manner inhibitory effect on TNF-α release, with better IC50 value (3.58 μM) than barbigerone (8.46 μM). Oral administration of 1g at 20 mg/kg/day for two weeks obviously demonstrated protective effect in adjuvant-induced arthritis models as evaluated by clinical score of paws, and histological examination of joint tissues from rats. Mechanism studies on mRNA and protein level suggested that 1g inhibited the TNF-α production via depressing TNF-α converting enzyme (TACE) mRNA expression. In conclusion, these data show 1g with potential therapeutic effects as an anti-inflammatory agent.

  DOI：

  10.1016/j.fitote.2014.06.002
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 吡啶 、 盐酸 、 水 、 sodium hydride 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 (E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  吡咯烷酮衍生物作为有效抗炎药的合理设计，合成和药理特性

  摘要：

  设计并评估了24种衍生自天然吡喃并二氢呋喃酮（I和II）的衍生物（5a – x）对LPS刺激的RAW264.7细胞中一氧化氮（NO）产生的抑制作用。其中，与阳性对照消炎痛相比，四种化合物（5b，5d，5f和5h）对iNOS活性和iNOS介导的NO产生更有效的抑制作用。而且5b与吲哚美辛相比，剂量为10 mg / kg / day的大鼠可显着抑制角叉菜胶诱发的后足水肿的进展，并通过关节炎评分和关节H＆E染色验证了剂量依赖性地改善了佐剂诱发的关节炎（AIA）的发展。此外，对接研究证实5b是与鼠iNOS活性位点结合的iNOS抑制剂。

  DOI：

  10.1016/j.ejmech.2012.05.005

文献信息

• Rhodium(III)-Catalyzed Dehydrogenative Heck Reaction of Salicylaldehydes
  作者：Zhuangzhi Shi、Nils Schröder、Frank Glorius

  DOI：10.1002/anie.201203224

  日期：2012.8.6

  RhIII‐catalyzed dehydrogenative Heck reaction (DHR) of salicylaldehydes with different classes of olefins extends the oxidative Heck reaction to aldehyde CH bonds. Several structural motifs similar to natural products and bioactive molecules such as aurones, flavones, 2′‐hydroxychalcones, and flavanones could be efficiently produced. Initial mechanistic studies give insight into the reaction mechanism.

  你的选择！水杨醛与不同种类烯烃的有效的Rh III催化脱氢Heck反应（DHR）将氧化Heck反应扩展至醛CH键。可以有效地产生类似于天然产物和生物活性分子的几种结构基序，例如金酮，黄酮，2'-羟基查耳酮和黄烷酮。初步的机理研究使人们深入了解了反应机理。
• A convenient and biogenetic type synthesis of few naturally occurring chromeno dihydrochalcones and their in vitro antileishmanial activity
  作者：Tadigoppula Narender、Shweta、Suman Gupta

  DOI：10.1016/j.bmcl.2004.05.071

  日期：2004.8

  2',2'-Dimethyl chromeno dihydrochalcones are very rare in nature as plant secondary metabolites. Recently we have reported three such compounds from the plant Crotalaria ramosissima. Chromeno dihydrochalcones contain a 2',2'-dimethyl benzopyran system, which are frequently encountered in many natural products and exhibit a variety of biological activities. We here report the strategy to conveniently synthesize naturally occurring chromeno dihydrochalcones by biogenetic type pyridine or Amberlyst-15 catalyzed chromenylation of dihydrochalcones and in vitro antileishmanial activity of chromeno dihydrochalcones and their intermediates. (C) 2004 Elsevier Ltd. All rights reserved.
• Isolation and synthesis of chalcones with different degrees of saturation
  作者：Karsten Krohn、Klaus Steingröver、M Srinivasa Rao

  DOI：10.1016/s0031-9422(02)00475-2

  日期：2002.12

  Crotaoprostrin, a chalcone not yet known as a plant constituent, was isolated from the aerial parts of the Indian medicinal plant Crotalaria prostrata. The structures of the chalcone polyarvin and the partially hydrogenated naturally occurring derivatives crotaramin, crotaramosmin, and crotin were confirmed by chemical synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Prenylated flavonoids and a dihydro-4-phenylcoumarinfrom Dorstenia poinsettifolia
  作者：Bonaventure T Ngadjui、Gilbert W.F Kapche、Helene Tamboue、Berhanu M Abegaz、Joseph D Connolly

  DOI：10.1016/s0031-9422(98)00621-9

  日期：1999.5

  The twigs of Dorstenia poinsettifolactone yielded poinsettifolactone, a new dihydro-4-phenylcoumarin, and dorspoinsettifolin, a new 7,8-(2,2-dimethylpyrano)-4'-methoxyflavanone. Three known prenylated flavonoids, 4-hydroxylonchocarpin, 4-methoxylonchocarpin and 4'-hydroxyisolonchocarpin, were also isolated and identified. Structures were established by spectroscopic analysis and chemical correlations. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A chalcone and an isoflavone from Millettia pachycarpa seeds
  作者：Ashok K. Singhai Nabin C.^Barua Ram P.^Sha

  DOI：10.1016/0031-9422(83)85042-0

  日期：——