4-hydroxy-3-(p-methoxycinnamoyl)coumarin | 57339-72-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-hydroxy-3-(p-methoxycinnamoyl)coumarin
• 英文别名: 4-Hydroxy-3-<3-(4-methoxy-phenyl)-acryloyl>-cumarin；1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-3-(4-methoxyphenyl)-2-propen-1-one；4-hydroxy-3-[3-(4-methoxy-phenyl)-acryloyl]-chromen-2-one；4-Hydroxy-3-[3-(4-methoxyphenyl)prop-2-enoyl]chromen-2-one
• CAS: 57339-72-7
• 化学式: C₁₉H₁₄O₅
• mdl: MFCD03019891
• 分子量: 322.317
• InChiKey: YHEBRAOEOLPKGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(p-methoxycinnamoyl)coumarin 在 乙酸酐 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-(4-hydroxycoumarin-3-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde
  参考文献：
  名称：

  分子间π···π相互作用在新型香豆素基吡唑啉材料的发光行为中的作用

  摘要：

  合成了九种基于香豆素的吡唑啉并对其进行了全面表征，以寻找用于设计刺激响应性铬材料的新型荧光化合物。所有报告的化合物在溶液和固态下均表现为高荧光物质，分子间相互作用在其光物理性质中起关键作用。特别是化合物1a由于分子间π··π过渡的建立和/或破裂而表现出不可逆的热，机械，溶剂化和气相致变色行为，此外，由于添加了几种金属而形成的络合，其离子致变色性质盐。粉末XRD研究已经进行，以解释所述的刺激反应效应。化合物1a分子具有π··π相互作用，这是通过六元环的质心之间的短距离3.61（2）Å和弱的分子间C–H…O氢键来证明的，这些分子将π···π二聚体连接到列。根据具有B3LYP功能的TD DFT方法的量子化学计算，以def2-TZVP为基础，分子间π···π相互作用导致1a的电子吸收（EA）发生强烈的红移（约63 nm）。固态。相反，在2a结构中，没有任何有关π···π堆积的提示，并且从溶液到固态

  DOI：

  10.1016/j.dyepig.2020.108942
• 作为产物：
  描述：

  4-羟基香豆素 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 4-hydroxy-3-(p-methoxycinnamoyl)coumarin
  参考文献：
  名称：

  新型吲哚基-香豆素杂种的抗leishmanial活性：设计，合成，生物学评估，分子对接研究和计算机模拟ADME。

  摘要：

  在目前的工作中，我们已经设计和合成了总共十二种新颖的3-（3-（1 H-吲哚-3-基）-3-苯基丙酰基）-4-羟基-2 H-铬-2--2-酮衍生物13（a – l），使用掺有Ho 3+的CoFe 2 O 4纳米颗粒作为催化剂，并评估了其潜在的抗菌活性和抗氧化活性。与标准的葡糖基葡萄糖酸钠（IC 50）相比，发现化合物13a，13d和13h具有显着的抗霉菌活性（IC 50值分别为95.50、95.00和99.00μg/ mL）。 = 490.00μg/ mL）。化合物13a（IC 50  = 12.40μg/ mL），13d（IC 50  = 13.49μg/ mL），13g（IC 50  = 13.24μg/ mL）和13l（IC 50  = 13.74μg/ mL）具有良好的抗氧化活性与标准丁基化羟基甲苯（IC 50  = 16.5μg/ mL）和抗坏血酸（IC 50  = 12.8μg/

  DOI：

  10.1016/j.bmcl.2015.12.085

文献信息

• Chalcone-based derivatives as new scaffolds for <i>h</i>A3 adenosine receptor antagonists
  作者：Saleta Vazquez-Rodriguez、Maria João Matos、Lourdes Santana、Eugenio Uriarte、Fernanda Borges、Sonja Kachler、Karl-Norbert Klotz

  DOI：10.1111/jphp.12028

  日期：2013.4.19

  With the aim of finding new adenosine receptor (AR) ligands based on the chalcone scaffold, we report the synthesis of a new series of coumarin–chalcone hybrids and the pharmacological characterization of their actions at four subtypes of AR.

  The synthesized compounds 5–10 were characterized in radioligand binding (A1, A2A and A3) and adenylyl cyclase activity assays (A2B) to determine the affinity of the compounds for the four human AR (hAR) subtypes.

  Coumarin–chalcone hybrids were found to be ligands with a novel structure, not reported thus far, that showed varying affinity and selectivity for AR subtypes.

  The coumarin–chalcone hybrids in which ring B of the chalcone scaffold was a thiophene (compounds 5 and 9) were found to be the most potent compounds of the series. Compound 9, in which ring A of the chalcone moiety was the phenyl ring of the coumarin, showed similar activity against hA1, hA2A and hA3 ARs, while compound 5, in which ring A of the chalcone was substituted by the benzopyrone ring of the coumarin moiety, showed similar activity only at the hA3 AR and, therefore, was deemed to be selective (Ki (dissociation constant) = 5160 nm).

  本研究旨在基于香豆素-查尔酮杂化结构，寻找新的腺苷受体（AR）配体。我们报道了一系列新的香豆素-查尔酮杂化物的合成，并对它们在四个AR亚型上的药理学特性进行了表征。

  通过放射性配体结合（A1、A2A和A3）和腺苷酸环化酶活性测定（A2B），对合成的5-10化合物进行表征，以确定这些化合物与四个人类AR亚型（hAR）的亲和力。

  发现香豆素-查尔酮杂化物是一种新颖的配体，具有不同的亲和力和选择性，这种结构以前尚未报道。

  在这个系列中，查尔酮结构的B环为噻吩的香豆素-查尔酮杂化物（化合物5和9）被发现是最有效的化合物。化合物9中，查尔酮部分的A环为香豆素的苯环，对hA1、hA2A和hA3 AR具有类似的活性；而化合物5中，查尔酮的A环被香豆素的苯并吡喃环取代，只对hA3 AR具有类似的活性，因此被认为是具有选择性的（Ki（解离常数）=5160 nm）。

• Evaluation of Structurally Diverse Benzoazepines Clubbed with Coumarins as<i>Mycobacterium tuberculosis</i>Agents
  作者：Kuldip Upadhyay、Atul Manvar、Kena Rawal、Sudhir Joshi、Jalpa Trivedi、Ravi Chaniyara、Anamik Shah

  DOI：10.1111/j.1747-0285.2012.01436.x

  日期：2012.12

  Tuberculosis caused by Mycobacterium tuberculosis remains a leading cause of mortality worldwide into 21st century. In continuation with our anti‐tuberculosis research programme, in this work, we have prepared molecularly diverse coumarins clubbed with benzothiazepines as well as its aza‐analogues‐benzodiazepines by molecular hybridization. The resulting compounds were screened for their M. tuberculosis activity against H37Rv strains using microplate alamar blue assay. Among the designed diversity, the compounds 5k, 5n and 5o were found significantly active in primary anti‐tuberculosis assay at minimum inhibitory concentration <6.25 μm. Moreover, the IC50 values of 5k and 5o in level‐2 screening were observed as >10 μg/mL and 3.63 μg/mL, respectively. Design and synthesis of more focused library and its three‐dimensional quantitative structure activity relationship analysis are underway.
• Mustafa,A. et al., Justus Liebigs Annalen der Chemie, 1965, vol. 684, p. 194 - 200
  作者：Mustafa,A. et al.

  DOI：——

  日期：——
• Design, synthesis and biological evaluation of some novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones as antimalarial agents
  作者：Kuldeep Patel、Chandrabose Karthikeyan、N. S. Hari Narayana Moorthy、Girdhar Singh Deora、Viswas Raja Solomon、Hoyun Lee、Piyush Trivedi

  DOI：10.1007/s00044-011-9694-1

  日期：2012.8

  A novel series of 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones were designed, synthesized and screened for antiplasmodial activity. Eleven compounds of the series exhibited micromolar potency against chloroquine sensitive and chloroquine resistant strains. The most potent compound 4-hydroxy-3-(3-(4-nitrophenyl)acryloyl)-2H-chromen-2-one showed inhibitory potency (IC50) of 3.1 and 4 mu g/ml against chloroquine sensitive and chloroquine resistant strains, respectively. A structure activity relationship study was performed by correlating the effect of substituents with the antimalarial activity of the title compounds. The novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones reported here should be good lead for further development of antimalarial agents that can overcome resistance.
• Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives
  作者：Omaima M. Abdelhafez、Kamelia M. Amin、Rasha Z. Batran、Timothy J. Maher、Somaia A. Nada、Shalini Sethumadhavan

  DOI：10.1016/j.bmc.2010.04.009

  日期：2010.5

  The action of the coumarin-type drugs and related compounds is reviewed to their VKOR antagonistic effects. In our study, twenty 3-pyridinyl, pyrimidinyl and pyrazolyl-4-hydroxycoumarin derivatives were synthesized. A comparative in vivo (CT, PT determination) and in vitro ( measurement of PIVKA-II levels) anticoagulant study with respect to warfarin showed that the synthesized compounds have different anticoagulant activities, the most prospective compounds were the 3-pyrazolyl-4-hydroxycoumarin derivatives. (C) 2010 Elsevier Ltd. All rights reserved.