2-oxo-4-phenyl-2H-chromen-7-ylbenzoate | 94739-93-2

• 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: 2-oxo-4-phenyl-2H-chromen-7-ylbenzoate
• 英文别名: 7-benzoyloxy-4-phenyl-coumarin；7-Benzoyloxy-4-phenyl-cumarin；2-oxo-4-phenyl-2H-chromen-7-yl benzoate；(2-oxo-4-phenylchromen-7-yl) benzoate
• CAS: 94739-93-2
• 化学式: C₂₂H₁₄O₄
• 分子量: 342.351
• InChiKey: UYQWSXYHSUHDDR-UHFFFAOYSA-N

物化性质

• 熔点：
  137 °C
• 沸点：
  532.7±50.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-oxo-4-phenyl-2H-chromen-7-ylbenzoate 在 三氯化铝 作用下， 生成 6-benzoyl-7-benzoyloxy-4-phenyl-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-乙酰氧基-4-苯基-色烯-2-酮 在 sodium hydroxide 作用下， 生成 2-oxo-4-phenyl-2H-chromen-7-ylbenzoate
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Synthesis, computational studies and assessment of <i>in vitro</i> inhibitory activity of umbelliferon-based compounds against tumour-associated carbonic anhydrase isoforms IX and XII
  作者：Francesca Mancuso、Laura De Luca、Andrea Angeli、Sonia Del Prete、Clemente Capasso、Claudiu T. Supuran、Rosaria Gitto

  DOI：10.1080/14756366.2020.1786821

  日期：2020.1.1

  resorcinol derivatives and suitable β-ketoesters. The evaluation of inhibitory activity revealed that these compounds possessed nanomolar affinity and high selectivity towards tumour-associated hCA IX and XII over cytosolic hCA I and hCA II isoforms. To investigate the binding mode of these new coumarin-inspired inhibitors, the most active compounds 10 and 17 were docked within hCA XII catalytic cleft.

  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。
• Anti-Influenza Drug Discovery: Structure−Activity Relationship and Mechanistic Insight into Novel Angelicin Derivatives
  作者：Jiann-Yih Yeh、Mohane Selvaraj Coumar、Jim-Tong Horng、Hui-Yi Shiao、Fu-Ming Kuo、Hui-Ling Lee、In-Chun Chen、Chun-Wei Chang、Wen-Fang Tang、Sung-Nain Tseng、Chi-Jene Chen、Shin-Ru Shih、John T.-A. Hsu、Chun-Chen Liao、Yu-Sheng Chao、Hsing-Pang Hsieh

  DOI：10.1021/jm901570x

  日期：2010.2.25

  By using a cell-based high throughput screening campaign,a novel angelicin derivative 6a was identified to inhibit influenza A (H1N1) virus induced Cytopathic effect in Madin-Darby canine kidney cell culture in low micromolar range. Detailed structure-activity relationship studies of 6a revealed that the angelicin scaffold is essential for activity in pharmacophore B, while meta-substituted phenyl/2-thiophene rings are optimal ill pharmacophore A and C. The optimized lead 4-methyl-9-phenyl-8-(thiophene-2-carbonyl)-furo[2,3-h]chromen-2-one (8g, IC50 = 70 nM) showed 64-fold enhanced activity compared to the high throughput screening (HTS) hit 6a. Also, 8g was found effective in case of influenza A (H3N2) and influenza B virus strains similar to approved anti-influenza drug zanamivir (4). Preliminary mechanistic studies suggest that these compounds act as anti-influenza agents by inhibiting ribonucleoprotein (RNP) complex associated activity and have the potential to be developed further, Which Could form the basis for developing additional defense against influenza pandemics.
• 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：——
• 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：——