异补骨脂色烯查耳酮标准品 | 56083-03-5

• 物质功能分类: 天然产物 - 查尔酮类化合物
• 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
• 中文名称: 异补骨脂色烯查耳酮标准品
• 中文别名: 异补骨脂色烯查耳酮
• 英文名称: 4-hydroxylonchocarpin
• 英文别名: (E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)-prop-2-en-1-one；(E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one；3',4'-(2,2-dimethylpyrano)-2',4-dihydroxychalcone；4-hydroxylsolonchocarpin；4-hydroxy-lonchocarpin；4-hydroxylonchocarpine；Isobavachromene；(E)-1-(5-hydroxy-2,2-dimethylchromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 56083-03-5
• 化学式: C₂₀H₁₈O₄
• 分子量: 322.361
• InChiKey: IQHPDUUSMBMDGN-WEVVVXLNSA-N

物化性质

• 熔点：
  203-204℃
• 沸点：
  535.1±50.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

生物活性方面，4-羟基黄酮香豆素（4-Hydroxylonchocarpin）是一种源自补骨脂（Psoralea corylifolia）提取物的查尔酮化合物。研究显示，它能够增强 p38 MAPK、JNK 和 ERK 的磷酸化水平。此外，这种化合物具有多种药理活性，包括抗菌、抗癌、抗逆转录酶、抗结核、抗疟疾、抗炎和抗氧化等作用。

反应信息

• 作为反应物：
  描述：

  异补骨脂色烯查耳酮标准品 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 (E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  查耳酮类化合物的合成及生物学评价

  摘要：

  已经研究了三十五个合成查尔酮的抗利什曼活性。其中，10个化合物（4，6，16，22，23，24，25，29，35和37）表现出体外活性有效的（IC 50范围为1.70〜8μM）对细胞外前鞭毛体和胞内无鞭毛体形成的利什曼原虫多诺瓦尼。在多诺尼乳杆菌/仓鼠模型中体内测试了两种有希望的化合物22和37。查尔酮37 在治疗后第7天，以50 mg / kg的剂量显示10天的寄生虫抑制率为83.32％，而以100 mg / kg的剂量显示5天的寄生虫抑制率为5天的75.89％。

  DOI：

  10.1016/j.ejmech.2014.05.034
• 作为产物：
  描述：

  β-tubaic acid 在 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 异补骨脂色烯查耳酮标准品
  参考文献：
  名称：

  A New Route to the Synthesis of Pyranoflavone and Pyranochalcone Natural Products and their Derivatives

  摘要：

  从2H-吡喃出发，完成了生物活性吡喃黄酮天然产物1和2的全合成。本文描述了吡喃查尔酮天然产物，扁柄草素（9）和4-羟基扁柄草素（10）及其衍生物30-32的合成。该合成路线还提供了生物学上有趣的物质，如β-图贝酸（24）、去甲基异黄皮树脂酚（25）和异黄皮树脂酚（27）。

  DOI：

  10.1055/s-2006-926294

文献信息

• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans
  作者：K. C. Nicolaou、J. A. Pfefferkorn、A. J. Roecker、G.-Q. Cao、S. Barluenga、H. J. Mitchell

  DOI：10.1021/ja002033k

  日期：2000.10.1

  report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran

  在此，我们报告了一种基于特权结构原理设计和构建天然和天然产物类库的新策略，该术语最初用于描述能够与各种不相关的分子靶标相互作用的结构基序。讨论了天然产物中此类特权结构的鉴定，随后选择 2,2-二甲基苯并吡喃部分作为通过该策略构建类天然产物库的初始模板。最初，采用独特的环加载策略开发了苯并吡喃基序的新型固相合成，该策略依赖于使用新的聚苯乙烯基溴化硒树脂。一旦确定了这些苯并吡喃的加载、加工和裂解，
• Hemisynthesis and Spectroscopic Characterization of Three New Chalcone Derivatives from Dorstenia barteri
  作者：Bathelemy Ngameni、Ghislain Wabo Fotso、Pantaleon Ambassa、Justin Kamga、Arif Dastan、Bonaventure Tchaleu Ngadjui

  DOI：10.1007/s10600-017-1962-y

  日期：2017.3

  The hemisynthesis of three new chalcones, namely kenzanol, kelianol A, and kelianol B, from Dorstenia barteri (Moraceae) is described here for the first time. The synthetic pathways employed in this work involved the pyrolysis and catalytic hydrogenation of readily available and starting materials, 4-hydroxylonchocarpin and isobavachalcone, two major constituents of the herbaceous plant D. barteri

  此处首次描述了来自 Dorstenia barteri（桑科）的三种新查耳酮的半合成，即 kenzanol、kelianol A 和 kelianol B。这项工作中采用的合成途径涉及容易获得的起始材料 4-羟基磷酰胆碱和异巴伐查酮（草本植物 D. barteri 的两种主要成分）的热解和催化氢化。所有化合物的结构解析均通过质谱、红外、紫外、一维和二维核磁共振分析进行，并与以前的报告进行比较。
• 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.
• Synthesis and biological evaluation of pyranoisoflavone derivatives as anti-inflammatory agents
  作者：Zhe Wei、Youzhe Yang、Caifeng Xie、Chunyan Li、Guangcheng Wang、Liang Ma、Mingli Xiang、Jian Sun、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.fitote.2014.06.002

  日期：2014.9

  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.
• Selenium-Based Solid-Phase Synthesis of Benzopyrans I: Applications to Combinatorial Synthesis of Natural Products
  作者：K. C. Nicolaou、Jeffrey A. Pfefferkorn、Guo-Qiang Cao

  DOI：10.1002/(sici)1521-3773(20000218)39:4<734::aid-anie734>3.0.co;2-i

  日期：2000.2.18