8-acetyl-7-hydroxy-4-phenyl-2H-chromen-2-one | 54431-18-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 8-acetyl-7-hydroxy-4-phenyl-2H-chromen-2-one
• 英文别名: 7-Hydroxy-8-acetyl-4-phenylcumarin；8-acetyl-7-hydroxy-4-phenyl-2H-1-benzopyran-2-one；8-acetyl-7-hydroxy-4-phenyl-2H-benzopyran-2-one；8-acetyl-7-hydroxy-4-phenyl-coumarin；8-Acetyl-7-hydroxy-4-phenyl-cumarin；8-acetyl-7-hydroxy-4-phenylchromen-2-one
• CAS: 54431-18-4
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: WQXIMVYXEFLLAN-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C(Solv: ethanol (64-17-5))
• 沸点：
  502.5±50.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-acetyl-7-hydroxy-4-phenyl-2H-chromen-2-one 生成 7-hydroxy-4-phenyl-8-(1-semicarbazono-ethyl)-coumarin
  参考文献：
  名称：

  Limaye; Munje, Rasayanam, 1937, vol. 1, p. 80,82

  摘要：

  DOI：
• 作为产物：
  描述：

  7-羟基-4-苯基香豆素 在 aluminum (III) chloride 、 硫酸 、 三乙胺 作用下， 反应 2.0h， 生成 8-acetyl-7-hydroxy-4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  伞形虫基化合物对与肿瘤相关的碳酸酐酶同工型IX和XII的体外抑制活性的合成，计算研究和评估。

  摘要：

  摘要 香豆素是广泛散布的次级代谢产物，具有多种生物学活性。已经确定，香豆素代表一类特殊的人类碳酸酐酶（hCA）抑制剂，具有独特的作用机制，涉及与非经典结合的氨基酸残基铺平了hCA催化位点的入口。在这里，我们报告的小编新的香豆素衍生物的合成7-11，15，17由间苯二酚衍生物和合适的β-酮酸酯通过经典的Pechmann缩合制备。抑制活性的评估表明，这些化合物相对于胞质hCA I和hCA II同种型具有纳摩尔摩尔亲和力和对肿瘤相关hCA IX和XII的高选择性。为了研究这些新的香豆素类抑制剂的结合方式，将活性最高的化合物10和17停靠在hCA XII催化裂隙内。

  DOI：

  10.1080/14756366.2020.1786821

文献信息

• Synthesis and biological activity of meso-tetrakis (2,10-dioxo-2H, 10H-pyrano [2,3-f] chromene-9-yl) porphyrins
  作者：V. Naveen Kumar、Y. Thirupathi Reddy、P. Narasimhareddy、B. Rajitha、E. De Clercq

  DOI：10.3998/ark.5550190.0007.f22

  日期：——

  Synthesis of meso-tetrakis (2, 10-dioxo-2H, 10H-pyrano[2,3-f] chromene-9-yl) porphyrins are synthesized directly by reaction of pyrrole with substituted 4-methyl-2,10-dioxo-2H, 10Hpyrano[2,3-f]chromene-9-carbaldehydes in dichloromethane / acid media. The aldehyde’s molar ratio was controlled to optimize the synthesis and purification of the desired porphyrins. This new series of porphyrins was characterized

  meso-tetrakis (2, 10-dioxo-2H, 10H-pyrano[2,3-f] chromene-9-yl) 卟啉的合成是通过吡咯与取代的 4-methyl-2,10-dioxo-反应直接合成的二氯甲烷/酸介质中的 2H, 10Hpyrano[2,3-f]chromene-9-carbaldehydes。控制醛的摩尔比以优化所需卟啉的合成和纯化。这个新系列的卟啉通过 TLC、质谱（FAB 质量）、H NMR、UV 和 IR 进行表征
• Synthesis, biological evaluation and docking studies of novel benzopyranone congeners for their expected activity as anti-inflammatory, analgesic and antipyretic agents
  作者：Amal A.M. Eissa、Nahla A.H. Farag、Gamal A.H. Soliman

  DOI：10.1016/j.bmc.2009.05.073

  日期：2009.7

  ne as starting material a number of 8-substituted derivatives (i.e., hydrazones 2a,b, imine 2c, chalcones 3, pyrazoles 4, 3-cyano-2-oxo-dihydropyridines 5, and/or 3-cyano-2-imino-dihydropyridines 6) were synthesized and assayed for their anti-inflammatory, analgesic and antipyretic activities. Compounds 3c, 4b and 4i showed significant anti-inflammatory, analgesic and antipyretic activities. In addition

  8-乙酰基-7-羟基-4-苯基-2- ħ苯并吡喃-2-酮作为起始原料的数8取代的衍生物（即，腙的图2a，b，亚胺2C，查耳酮3，吡唑4，3-氰基合成了-2-氧代二氢吡啶5和/或3-氰基-2-亚氨基二氢吡啶6，并测定了它们的抗炎，镇痛和解热活性。化合物3c，4b和4i显示出显着的抗炎，止痛和解热活性。此外，1，3B，4D，4E，5b，6a，6c，6d，6e表现出抗炎作用，2b，4h，5e表现出镇痛作用，2b，4h，5e表现出退烧作用。此外，为了预测合成化合物在活性位点的亲和力和方向，使用molsoft icm 3.4-8C程序对被测化合物与其结合的抑制剂吲哚美辛（4COX）复合的环加氧酶II进行了分子建模和对接。此外，人们发现，活性化合物1，4I，6a – e与丝氨酸530和酪氨酸385氨基酸相互作用，这是参与环氧合酶II抑制机制的主要氨基酸。 含吡唑的新化合物4的合成证明成功。同样，3-氰
• Kulshrestha, S.K.; Dureja, P.; Mukerjee, S.K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 11, p. 1064 - 1067
  作者：Kulshrestha, S.K.、Dureja, P.、Mukerjee, S.K.

  DOI：——

  日期：——
• Design, synthesis and docking studies of new furobenzopyranones and pyranobenzopyranones as photoreagent towards DNA and as antimicrobial agents
  作者：Nahla A.H. Farag、Wafaa El-Tayeb

  DOI：10.1016/j.ejmech.2009.10.016

  日期：2010.1

  A number of new furobenzopyranones and pyranobenzopyranones carrying an electron- withdrawing function at the position 3 are synthesized in order to obtain new photoreagents towards DNA. Our interest in this study is to investigate the effect of introduction of electron withdrawing function on the position 3 of the benzo-a-pyrranone ring of linear furobenzo-a-pyranone (5,8-dimethoxypsoralen) or angular pyranobenzo-a-pyranone on the biological activity, by preparing 3-cyano, carboxylic acid, carboxylic acid ester, acid hydrazide, thiosemicarbazide, or mercaptotriazole derivatives. 5-acetyl-6-hydroxybenzofuran, and 8-acetyl-7-hydroxy-4-phenylbenzopyranone are the key starting compounds on which 3-cyano-4-methylfurobenzopyranone and 3-cyano-4-methyl pyranobenzopyranone moieties were built respectively. The photobiological activity of the newly synthesized compounds was evaluated. It looks most promising for enhancement of photoreactivity of compounds towards DNA, and a certain effect was observed in the dark determining the antimicrobial activity.Compounds 5, 6, 7, 13, 14 exhibit potential photoreactivity, towards DNA, while 3-mercaptotriazole derivatives 7,14 possess only photosensitizing activity.To investigate the antimicrobial data on structural basis, molecular modelling and docking studies of the tested compounds into the crystal structure of topoisomerase II DNA Gyrase B complexed with the natural inhibitor bearing the coumarin moiety clorobiocin (1kzn), using Molsoft ICM 3.4-8C program was performed in order to predict the affinity and orientation of the synthesized compounds at the active site. The ICM score values and hydrogen bonds formed with the surrounding amino acids show good agreement with predicted binding affinities obtained by molecular docking studies as verified by antimicrobial screening, where compounds 5, 6,13 were the most active compounds against Bacillus subtilis, Staphylococcus aureus, and Escherichia coli. Compound 13 has good affinity with the receptor and forms six hydrogen bonds with Asp-73. and two bonds with Thr-165, compound 6 has ICM score value -85.66 and forms one hydrogen bond with Asp-73, and three with Thr-165, and compound 5 has ICM score value -53 but forms one hydrogen bond with Asp-73, and four bonds with Thr-165 which may reveal the potent antimicrobial activity referred to the natural antimicrobial Clorobiocin which forms two hydrogen bonds with Asp-73 and three with Thr-165. (C) 2009 Elsevier Masson SAS. All rights reserved.
• REHSE K.; SCHNAEDELBACH S.; RIETBROCK N.; GRUBER F., ARCH. PHARM. <APBD-AJ>, 1978, 311, NO 1, 52-58
  作者：REHSE K.、 SCHNAEDELBACH S.、 RIETBROCK N.、 GRUBER F.

  DOI：——

  日期：——