6-(3,4,5-trimethoxyphenyl)-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile | 905577-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(3,4,5-trimethoxyphenyl)-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile
• 英文别名: 4-Methylsulfanyl-2-oxo-6-(3,4,5-trimethoxyphenyl)pyran-3-carbonitrile
• CAS: 905577-87-9
• 化学式: C₁₆H₁₅NO₅S
• 分子量: 333.365
• InChiKey: WETOVOKIUCDJRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(3,4,5-trimethoxyphenyl)-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile 在 肼 作用下， 以 甲醇 为溶剂， 以74%的产率得到2-(5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl)acetonitrile
  参考文献：
  名称：

  高荧光吡唑和咪唑杂环的光物理和电化学研究

  摘要：

  研究了高度稠合的吡唑和咪唑环含杂环的光物理和电化学性质。在DMF介质中使用B3LYP / G（d，p）能级理论对分子进行TDDFT计算，结果与实验值吻合良好。咪唑衍生物显示出红移吸收峰（λ最大，455-474纳米）和较高的摩尔消光系数大于吡唑衍生物。在从吡唑到咪唑的π共轭增加的情况下，观察到发射最大值（537nm-565nm）中的红移。吸收和发射光谱的这些初步结果表明，这些分子可能具有有机应用的潜力。

  DOI：

  10.1016/j.dyepig.2016.09.030
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 2-氰-3,3-二(甲硫基)丙烯酸甲酯 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 6-(3,4,5-trimethoxyphenyl)-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  高荧光吡唑和咪唑杂环的光物理和电化学研究

  摘要：

  研究了高度稠合的吡唑和咪唑环含杂环的光物理和电化学性质。在DMF介质中使用B3LYP / G（d，p）能级理论对分子进行TDDFT计算，结果与实验值吻合良好。咪唑衍生物显示出红移吸收峰（λ最大，455-474纳米）和较高的摩尔消光系数大于吡唑衍生物。在从吡唑到咪唑的π共轭增加的情况下，观察到发射最大值（537nm-565nm）中的红移。吸收和发射光谱的这些初步结果表明，这些分子可能具有有机应用的潜力。

  DOI：

  10.1016/j.dyepig.2016.09.030

文献信息

• Synthesis and fluorescence of 2<i>h</i>-pyrone derivatives for organic light-emitting diodes (OLED)
  作者：Naoko Mizuyama、Yuka Murakami、Shinya Kohra、Kazuo Ueda、Kyoko Hiraoka、Yoshinori Tominaga、Junko Nagaoka、Kojiro Takahashi、Yasuhiro Shigemitsu

  DOI：10.1002/jhet.5570440120

  日期：2007.1

  2H-Pyrone derivatives were synthesized through the reaction of aryl acetyl compounds with ketene dithioacetals in the presence of sodium hydroxide, and they showed very strong fluorescence in the solid state. The light-emitting region of these 2H-pyrones is 447-630 nm in the solid states.

  2 H-吡喃酮衍生物是通过芳基乙酰基化合物与乙烯酮二硫缩醛在氢氧化钠的存在下反应合成的，它们在固态时显示出非常强的荧光。在固态下，这两个H-吡喃酮的发光区域为447-630 nm。
• Reaction of 6‐aryl‐ or styryl‐4‐methylsulfanyl‐2‐oxo‐2<i>H</i>‐pyrans with active methylene compounds and fluorescence properties of the products
  作者：Naoko Mizuyama、Yuka Murakami、Takatoshi Nakatani、Keiko Kuronita、Shinya Kohra、Kazuo Ueda、Kyoko Hiraoka、Yoshinori Tominaga

  DOI：10.1002/jhet.5570450133

  日期：2008.1

  Abstractmagnified imageNew 2‐pyrone derivatives, dialkyl 3‐cyano‐6‐phenyl‐2‐oxo‐2H‐pyran‐4‐ylmalonates and alkyl 3‐cyano‐6‐phenyl‐2‐oxo‐2H‐pyran‐4‐ylacetates, which were easily prepared by the reaction of 6‐aryl‐4‐methyl‐sulfanyl‐2‐oxo‐2H‐pyran‐3‐carbonitriles with active methylene compounds in the presence of potassium carbonate, show fluorescence emission radiation. The light‐emitting region of dimethyl 3‐cyano‐6‐(4‐N,N‐dimethylamino)styryl‐2‐oxo‐2H‐pyran‐4‐ylmalonate (7h) was 620 nm in dichloromethane, making this compound a typical red fluorescent compound. Methyl 8‐hydroxy‐6‐methyl‐1‐oxo‐3‐phenyl‐1H‐pyrano‐[3,4‐c]pyridine‐5‐carboxylate deriv‐atives also showed fluorescence in the solid state. This is the first example of fluorescence in fused 2‐pyrone derivatives.
• New Fluoranthene FLUN-550 as a Fluorescent Probe for Selective Staining and Quantification of Intracellular Lipid Droplets
  作者：Atul Goel、Ashutosh Sharma、Manoj Kathuria、Arindam Bhattacharjee、Ashwni Verma、Prabhat R. Mishra、Aamir Nazir、Kalyan Mitra

  DOI：10.1021/ol403470d

  日期：2014.2.7

  A new class of live cell permeant, nontoxic fluoranthene-based fluorescent probe (FLUN-550) having a high Stokes shift in aqueous medium has been discovered. It showed selective staining of lipid droplets (LDs, dynamic cytoplasmic organelles) at a low concentration without background noise in in vitro live cell imaging of 3T3-L1 preadipocytes, J774 macrophages, MCF7 breast cancer cells, and single-celled, parasitic protozoa Leishmania donovani promastigotes and in vivo nonparasitic soil nematode C. elegans.
• A carbanion induced synthesis of highly congested pyrazole and imidazole containing heterocycles
  作者：Hardesh K. Maurya、Atul Gupta

  DOI：10.1016/j.tetlet.2014.01.095

  日期：2014.3

  An efficient approach to the synthesis of highly congested di, penta and hexacyclic pyrazoles as well as imidazole fragment containing novel heterocyclic molecule has been developed through a carbanion induced transformation of suitably functionalized 2H-pyran-2-ones, benzo[h]chromene and thiochromeno[4,3-b]pyrans. Due to the presence of fluorescence, we report their prime application metal sensor as off/on switching in ferric ions. (C) 2014 Elsevier Ltd. All rights reserved.
• A synthetic compound, 4-acetyl-3-methyl-6-(3,4,5-trimethoxyphenyl)pyrano[3,4-c]pyran-1,8-dione, ameliorates ovalbumin-induced asthma
  作者：Hwan-Suck Chung、Youngeun Kim、Sei Joong Oh、Hankyum Kim、Seung Ill Choi、Yujuan Zhang、Jin-Hyun Jeong、Hyunsu Bae

  DOI：10.1016/j.bmc.2013.08.045

  日期：2013.11

  Eosinophilia is one of the characteristic signs of allergic inflammation. Massive migration of eosinophils to the airways can cause epithelial tissue injury, contraction of airway smooth muscle and increased bronchial responsiveness. Previously, we discovered a new compound, 1H,8H-pyrano[3,4-c]pyran-1,8-dione (PPY), derived from the fruit of Vitex rotundifolia L. and evaluated its anti-inflammatory and anti-asthmatic properties. In this study, we synthesized a new modified compound, 4-acetyl-3-methyl-6-(3,4,5-trimethoxyphenyl)pyrano[3,4-c]pyran-1,8-dione (PPY-345), which was based on the PPY skeleton, and we evaluated its anti-asthmatic effects. To evaluate the anti-asthmatic effect of PPY-345 in vitro, A549 lung epithelial cells were stimulated with TNF-alpha, IL-4 and IL-1-beta to induce the expression of CCL11 (Eotaxin), a chemokine involved in eosinophil chemotaxis. To characterize the anti-asthmatic properties of PPY-345 in vivo, we examined the influence of PPY-345 in an ovalbumin (OVA)-induced asthma model. PPY-345 treatments significantly reduced CCL11 secretion. PPY-345 treatment did not inhibit the translocation of NF-kappa B into the nucleus but suppressed the phosphorylation of signal transducers and activators of transcription 6 (STAT6). PPY-345 treatment significantly reduced airway hyper-reactivity as measured by whole-body plethysmography. PPY-345 further reduced total cells, including eosinophil, macrophage and lymphocytes, in the BAL fluid, goblet cell hyperplasia and myosin light chain 2 positive smooth muscle cell area in the lung tissue. Additionally, PPY-345 significantly suppressed the levels of OVA-IgE present in the serum. These results suggested that PPY-345 could improve asthma symptoms in OVA-sensitized mice. (C) 2013 Elsevier Ltd. All rights reserved.