(E)-2-(4-methoxystyryl)-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-2-(4-methoxystyryl)-4H-chromen-4-one
• 英文别名: 4'-methoxy-2-styrylchromone；2-[(1E)-2-(4-methoxyphenyl)ethenyl]-4H-1-benzopyran-4-one；2-[(E)-2-(4-methoxyphenyl)vinyl]chromen-4-one；2-[(E)-2-(4-methoxyphenyl)ethenyl]chromen-4-one
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: SNRMIADKIKDZCS-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-2-(4-methoxystyryl)-4H-chromen-4-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到2-[(E)-2-(4-Hydroxy-phenyl)-vinyl]-chromen-4-one
  参考文献：
  名称：

  (E)-2-Styrylchromones as potential anti-norovirus agents

  摘要：

  Human noroviruses (NoV) are now recognized as the most frequent cause of outbreaks and sporadic cases of acute gastroenteritis. Despite the significant economic impact and considerable morbidity of norovirus disease, no drug or vaccine is currently available to treat or prevent this disease, therefore the discovery of anti-norovirus drugs is urgent.In the present work, a total of 12 structure related chromone and (E)-2-styrylchromones were evaluated for their potential anti-norovirus activity using the murine norovirus (MNV) as a surrogate model for human NoV.From the 12 compounds studied, six (E)-2-styrylchromones were found to have with interesting antinorovirus activity. The best compounds of the series were (E)-5-hydroxy-2-styrylchromone and (E)-4'-methoxy-2-styrylchromone with an IC50 approximate to 7 mu M. A first insight into the mechanism of action of these compounds was possible. An interesting relationship between the anti-norovirus activity and the chemical structure was observed. The present study points out that the (E)-2-styrylchromones skeleton is an important one which deserves to be developed and further explored as new antiviral drugs against NoV. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.006
• 作为产物：
  描述：

  (E)-3-(4-methoxyphenyl)acrylic anhydride 在 四丁基硫酸氢铵 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 1.5h， 生成 (E)-2-(4-methoxystyryl)-4H-chromen-4-one
  参考文献：
  名称：

  Makrandi, J. K.; Kumari, Vandna, Synthetic Communications, 1989, vol. 19, # 11-12, p. 1919 - 1922

  摘要：

  DOI：

文献信息

• Rh-Catalyzed aldehydic C–H alkynylation and annulation
  作者：Maddali L. N. Rao、Boddu S. Ramakrishna

  DOI：10.1039/c9ob02670c

  日期：——

  aldehydic C-H bond alkynylation and annulation for the in situ synthesis of chromones and aurones are described. It involves the sequential aldehyde C-H bond alkynylation of salicylaldehyde with in situ generated 1-bromoalkyne from 1,1-dibromoalkene followed by annulation. This protocol shows good functional group tolerance including aryl, alkenyl, alkyl and heteroaryl-1,1-dibromoalkenes. The steric/electronic

  描述了新颖的Rh催化醛CH键炔化和环化原位合成色酮和aurones。它涉及水杨醛与由1,1-二溴烯烃原位生成的1-溴炔烃进行的连续醛CH键炔化反应，然后进行环化。该协议显示出良好的官能团耐受性，包括芳基，烯基，烷基和杂芳基-1,1-二溴烯烃。在邻位羟基炔酮的碱介导的原位环化过程中证明了空间/电子效应，以生成金酮。
• Structure elucidation of a series of fluoro-2-styrylchromones and methoxy-2-styrylchromones using 1D and 2D NMR spectroscopy
  作者：Mehbub Momin、Deresh Ramjugernath、Neil A. Koorbanally

  DOI：10.1002/mrc.4111

  日期：2014.9

  the NMR data for 2-SCs are always reported in synthetic publications that also report the biological activity, full structural elucidation of these compounds is rare. We have only noticed one publication on the structural elucidation of this class of compounds in which the nitro derivatives were described. To the best of our knowledge, there are no publications where the structural elucidation of these

  2-苯乙烯基色酮 (2-SCs) 是含氧杂环化合物的化学家族，类似于黄酮类化合物 (2-苯基色酮)，但带有乙烯基将色酮环与苯基部分桥接。已经合成了许多 2-SCs 的衍生物，并且也报道了它们在自然界中的存在。也有许多关于 2-SCs 合成衍生物的生物活性的报道，最近 Gomes 等人对其进行了综述，这些化合物被认为具有抗氧化、抗病毒、抗癌、抗过敏和保肝活性，并显示出A3腺苷受体拮抗剂和黄嘌呤氧化酶抑制剂。尽管 2-SCs 的 NMR 数据总是在也报告生物活性的合成出版物中报道，但这些化合物的完整结构解析很少见。我们只注意到一篇关于这类化合物结构解析的出版物，其中描述了硝基衍生物。据我们所知，没有出版物讨论了这些化合物的结构解析，其中芳香环上的取代基通过共振向芳香环中提供电子。此外，氟化分子的结构解析更具挑战性，因为 F 具有 NMR 活性并与质子和碳原子偶联。我们最近报道了这些化合物的合成和抗菌活性，并在此报道了
• 2-Styrylchromone derivatives as potent and selective monoamine oxidase B inhibitors
  作者：Koichi Takao、Saki Endo、Junko Nagai、Hitoshi Kamauchi、Yuri Takemura、Yoshihiro Uesawa、Yoshiaki Sugita

  DOI：10.1016/j.bioorg.2019.103285

  日期：2019.11

  A series of eighteen 2-styrylchromone derivatives (see Chart 1) were synthesized and evaluated for their monoamine oxidase (MAO) A and B inhibitory activities. Many of the derivatives inhibited MAO-B comparable to pargyline (a positive control), and most of them inhibited MAO-B selectively. Of the eighteen derivatives, compound 9 having methoxy group at R1 and chlorine at R4 showed both the best MAO-B

  合成了18种2-苯乙烯基色酮衍生物（见图1），并评估了它们的单胺氧化酶（MAO）A和B抑制活性。与衍生物（阳性对照）相比，许多衍生物抑制MAO-B的作用，而且大多数都选择性抑制MAO-B。在这18种衍生物中，在R 1上具有甲氧基和在R 4上具有氯的化合物9表现出最佳的MAO-B抑制活性（IC 50  = 17±2.4 nM）和最佳的MAO-B选择性（IC 50对MAO-A而言） / IC 50（对于MAO-B = 1500）。化合物9的抑制方式对MAO-B的竞争是可逆的。使用分子操作环境（MOE）和Dragon使用2-苯乙烯基色酮衍生物的pIC 50值进行了定量构效关系（QSAR）分析，证明了MAO-B抑制活性和MAO-B选择性的描述分别为1734和121，显示出显着的相关性（P <0.05）。然后，我们通过使用AutoGPA的三维QSAR研究，将2-苯乙烯基色酮结构作为有用的支架进行了研
• Photochemistry of Flavonoids. V. Photocyclization of 2-Styryl-4H-chromen-4-ones
  作者：ICHIRO YOKOE、KYOKO HIGUCHI、YOSHIAKI SHIRATAKI、MANKI KOMATSU

  DOI：10.1248/cpb.29.2670

  日期：——

  Irradiation of 2-styryl-4H-chromen-4-ones (1) with a high pressure Hg lamp at room temperature under air gave benzo [α] xanthones (2). The cyclization of methoxy-substituted styrylchromones occurred at the para position relative to the OMe group on the styryl ring, whereas 2-[β-(2-naphthyl) vinyl] chromone (3) cyclized at the α-position of the naphthalene ring.

  在室温空气中用高压汞灯辐照 2-苯乙烯基-4H-苯并吡喃-4-酮 (1)，可得到苯并 [α]黄酮 (2)。甲氧基取代的苯乙烯基色酮的环化发生在苯乙烯基环上相对于 OMe 基团的对位，而 2-[β-（2-萘基）乙烯基]色酮（3）则在萘环的 α 位发生环化。
• (E)-3-Halo-2-styryl-4H-chromen-4-ones: synthesis and transformation to novel pyrazoles
  作者：Joana P.A. Ferreira、Vera L.M. Silva、José Elguero、Artur M.S. Silva

  DOI：10.1016/j.tet.2013.09.028

  日期：2013.11

  3(5)-aryl-5(3)-[2-(2-hydroxyphenyl)-2-hydrazonoethyl]-1H-pyrazoles, which upon acid hydrolysis gave 3(5)-aryl-5(3)-[2-(2-hydroxyphenyl)-2-oxoethyl]-1H-pyrazoles. The reaction mechanisms for these transformations, involving 1,6- followed by 1,4-conjugate additions, are discussed and the structures of all new compounds were established by NMR studies.

  用于合成新方法（ê）-3-卤代-2-苯乙烯基-4- ħ -苯并吡喃-4-酮来建立。这些化合物与水合肼反应，得到新的和意想不到的3（5） -芳基-5-（3） - [2-（2-羟基苯基）-2- hydrazonoethyl] -1- ħ -pyrazoles，其在酸水解，得到3（ 5） -芳基-5-（3） - [2-（2-羟基苯基）-2-氧代乙基] -1- ħ -pyrazoles。这些转化反应机理，涉及1,6-随后1,4-共轭加成，进行了讨论，并通过NMR研究建立的所有新化合物的结构。