(E)-4-hydroxy-6-styryl-2H-pyran-2-one | 2082-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-hydroxy-6-styryl-2H-pyran-2-one
• 英文别名: 2-Pyranone, 4-hydroxy-6-(2-phenylethenyl)-, (E)-；4-hydroxy-6-[(E)-2-phenylethenyl]pyran-2-one
• CAS: 2082-94-2
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: LGSQMZHPXAWUAT-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-hydroxy-6-styryl-2H-pyran-2-one 在 三乙胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (E)-4-(cyclohexylamino)-6-styryl-2H-pyran-2-one
  参考文献：
  名称：

  Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity

  摘要：

  4-Amino-2H-benzo[h] chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H-benzo[h] chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.084
• 作为产物：
  描述：

  反式-肉桂酸乙酯 在 正丁基锂 、 四甲基乙二胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 22.0h， 生成 (E)-4-hydroxy-6-styryl-2H-pyran-2-one
  参考文献：
  名称：

  5,6-脱氢卡哇因和一些氟化类似物的合成

  摘要：

  摘要报道了一种以四步顺序合成 6-苯乙烯基吡喃酮的有效方法。反应在无催化剂条件下使用温和且负担得起的试剂进行，以多克规模生产 5,6-脱氢卡瓦因和氟化衍生物，总产率良好至极好（72-86%）。这里首次报道了两种新型二氟化衍生物。图形概要

  DOI：

  10.1080/00397911.2018.1455212

文献信息

• P21-ACTIVATED KINASE INHIBITOR
  申请人：Biosystem Consulting Limited Company

  公开号：US20170349548A1

  公开（公告）日：2017-12-07

  The present invention addresses the problem of providing an inhibitor which has an excellent inhibitory activity on a p21-activated kinase. The present invention, by which has been solved the above-mentioned problem, is a p21-activated kinase 1 inhibitor containing, as an active ingredient, one or more compounds selected from the group consisting of dehydrokawain compounds, derivatives of dehydrokawain compounds, mimosine, derivatives of mimosine, and cucurbitacin compounds.

  本发明解决了提供一种对p21激活激酶具有优异抑制活性的抑制剂的问题。本发明解决了上述问题，是一种包含从去氢肉豆蔻化合物、去氢肉豆蔻化合物的衍生物、藜氨酸、藜氨酸的衍生物和葫芦巴碱化合物组成的群体中选择的一种或多种化合物作为活性成分的p21激活激酶1抑制剂。
• Enantioselective Biomimetic Total Syntheses of Katsumadain and Katsumadain C
  作者：Pengtao Zhang、Yongguang Wang、Ruiyang Bao、Tuoping Luo、Zhen Yang、Yefeng Tang

  DOI：10.1021/ol2029433

  日期：2012.1.6

  Enantioselective total syntheses of katsumadain and katsumadain C were achieved concisely through a biomimetic approach. Assembly of styryl-2-pyranone (3) and monoterpene 6 via acid-promoted regio- and stereoselective C–C bond formation afforded katsumadain (2), which underwent the photoinduced [2 + 2] dimerization in a head-to-tail mode to furnish katsumadain C (1).

  通过仿生方法简明地实现了胜肽和胜肽C的对映选择性合成。通过酸促进的区域和立体选择性C–C键形成的苯乙烯-2-吡喃酮（3）和单萜6的组装提供了胜马丹（2），其以从头到尾的方式经历了光诱导的[2 + 2]二聚化。提供katsumadain C（1）。
• Synthesis of 6-Substituted 4-Hydroxy-2-pyrones from Aldehydes by Addition of an Acetoacetate Equivalent, Dess-Martin Oxidation and Subsequent Cyclization
  作者：Thorsten Bach、Stefan Kirsch

  DOI：10.1055/s-2001-18759

  日期：——

  A three step procedure for the synthesis of 6-substituted 4-hydroxy-2-pyrones 2 from aldehydes 1 is described. An acetoacetate equivalent 3 was added to the corresponding aldehyde (10 examples) in a vinylogous Mukaiyama aldol addition (72-99%). The intermediate alcohols 4 were oxidized to the ketones 5 using the Dess-Martin method (67%-quant.). A final thermal cyclization of compounds 5 yielded the title compounds 2 (61-92%; 40-85% overall).

  描述了一种从醛1合成6-取代的4-羟基-2-吡喃酮2的三步程序。向相应的醛中加入了一种乙酰乙酸酯等效物3（10个例子）进行维尼洛戈斯Mukaiyama aldol加成（72-99%）。中间醇4通过Dess-Martin方法被氧化为酮5（67%-量）。最后对化合物5进行热环化反应，得到了目标化合物2（61-92%；整体转换率为40-85%）。
• Anti-Obesity Effects of Hispidin and Alpinia zerumbet Bioactives in 3T3-L1 Adipocytes
  作者：Pham Tu、Shinkichi Tawata

  DOI：10.3390/molecules191016656

  日期：——

  Obesity and its related disorders have become leading metabolic diseases. In the present study, we used 3T3-L1 adipocytes to investigate the anti-obesity activity of hispidin and two related compounds that were isolated from Alpinia zerumbet (alpinia) rhizomes. The results showed that hispidin, dihydro-5,6-dehydrokawain (DDK), and 5,6-dehydrokawain (DK) have promising anti-obesity properties. In particular, all three compounds significantly increased intracellular cyclic adenosine monophosphate (cAMP) concentrations by 81.2% ± 0.06%, 67.0% ± 1.62%, and 56.9% ± 0.19%, respectively. Hispidin also stimulated glycerol release by 276.4% ± 0.8% and inhibited lipid accumulation by 47.8% ± 0.16%. Hispidin and DDK decreased intracellular triglyceride content by 79.5% ± 1.37% and 70.2% ± 1.4%, respectively, and all three compounds inhibited glycerol-3-phosphate dehydrogenase (GPDH) and pancreatic lipase, with hispidin and DDK being the most potent inhibitors. Finally, none of the three compounds reduced 3T3-L1 adipocyte viability. These results highlight the potential for developing hispidin and its derivatives as anti-obesity compounds.

  肥胖及其相关疾病已成为主要的代谢性疾病。 在本研究中，我们利用 3T3-L1 脂肪细胞研究了从高山植物根茎中分离出的糙硬毛甙和两种相关化合物的抗肥胖活性。结果表明，Hispidin、二氢-5,6-脱氢卡瓦胡椒素（DDK）和 5,6-脱氢卡瓦胡椒素（DK）具有良好的抗肥胖特性。特别是，这三种化合物都能显著提高细胞内环磷酸腺苷（cAMP）浓度，分别为 81.2% ± 0.06%、67.0% ± 1.62% 和 56.9% ± 0.19%。此外，海司丁还能刺激甘油释放（276.4% ± 0.8%），抑制脂质积累（47.8% ± 0.16%）。Hispidin和DDK分别降低了细胞内甘油三酯含量（79.5% ± 1.37%）和（70.2% ± 1.4%），这三种化合物都能抑制甘油-3-磷酸脱氢酶（GPDH）和胰脂肪酶，其中Hispidin和DDK的抑制作用最强。最后，这三种化合物都没有降低 3T3-L1 脂肪细胞的活力。这些结果凸显了开发糙硬毛甙及其衍生物作为抗肥胖化合物的潜力。
• Reshaping the 2‐Pyrone Synthase Active Site for Chemoselective Biosynthesis of Polyketides
  作者：Yu Zhou、Evan N. Mirts、Sangdo Yook、Matthew Waugh、Rachel Martini、Yong‐Su Jin、Yi Lu

  DOI：10.1002/anie.202212440

  日期：2023.1.26

  Implementation of novel synthetic pathways into metabolic network is challenging. Empowered by protein engineering and synthetic biology, a whole-cell transformation process is reported to utilize engineered 2-pyrone synthase with novel reactivity in metabolic networks to convert carboxylic acids and intracellular malonyl-CoA directly into the pyrone products with high yields, catalytic efficiency and good selectivity

  将新的合成途径实施到代谢网络中具有挑战性。据报道，在蛋白质工程和合成生物学的支持下，全细胞转化过程利用在代谢网络中具有新颖反应性的工程化 2-吡喃酮合酶，将羧酸和细胞内丙二酰辅酶 A 直接转化为吡喃酮产品，具有高产率、催化效率和良好的选择性。