7-hydroxy-2-(4'-methoxy)phenyl-3-(4"-methoxy)benzoylchromone | 673475-94-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 7-hydroxy-2-(4'-methoxy)phenyl-3-(4"-methoxy)benzoylchromone
• 英文别名: 7-hydroxy-3-(4-methoxybenzoyl)-2-(4-methoxyphenyl)-4H-chromen-4-one；7-hydroxy-2-(4'-methoxyphenyl)-3-(4''-methoxybenzoyl)chromone；7-Hydroxy-3-(4-methoxybenzoyl)-2-(4-methoxyphenyl)chromen-4-one；7-hydroxy-3-(4-methoxybenzoyl)-2-(4-methoxyphenyl)chromen-4-one
• CAS: 673475-94-0
• 化学式: C₂₄H₁₈O₆
• 分子量: 402.403
• InChiKey: YBNQMDSYXFCWKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-hydroxy-2-(4'-methoxy)phenyl-3-(4"-methoxy)benzoylchromone 、 苯甲酰氯 在 吡啶 作用下， 反应 5.0h， 以25%的产率得到7-benzoate-2-(4'-methoxy)phenyl-3-(4"-methoxy)benzoylchromone
  参考文献：
  名称：

  Synthesis, Topoisomerase I Inhibitory and Cytotoxic Activities of Chromone Derivatives

  摘要：

  根据对接模拟研究，设计了一系列铬酮衍生物作为潜在的拓扑异构酶 I（Top I）抑制剂。对合成的 16 个化合物进行了拓扑异构酶 I 抑制活性评估，并进一步对一些化合物进行了体外细胞毒性测试。最有效的抑制剂色酮 11b 比已知的 Top I 抑制剂喜树碱、鱼藤素和吗啉具有更强的抑制活性（IC50 = 1.46 μM），但对乳腺癌细胞（MCF-7）、口腔癌细胞（KB）和小细胞肺癌（NCI-H187）没有活性。Chromone 11c 是另一种强效抑制剂（IC50 = 6.16 μM），对 KB（IC50 = 73.32 μM）和 NCI-H187 （IC50 = 36.79 μM）具有细胞毒性活性。

  DOI：

  10.2174/1573406411309030003
• 作为产物：
  描述：

  7-(4'''-methoxy)benzoate-2-(4'-methoxy)phenyl-3-(4"-methoxy)benzoylchromone 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 7-hydroxy-2-(4'-methoxy)phenyl-3-(4"-methoxy)benzoylchromone
  参考文献：
  名称：

  Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor

  摘要：

  Novel chromone derivatives with a benzopyran-4-one scaffold have been prepared by the one-pot cyclization reaction. The in vitro inhibitory activity of these new compounds towards HIV-1 protease have been evaluated using stop time HPLC method as the preliminary screening. The most potent compound, 7,8-dihydroxy-2-(3'-trifluoromethyl phenyl)-3-(3 ''-trifluoromethylbenzoyl)chromone (32), showed IC50 = 0.34 mu M. The molecular docking study supported results from experimental activity testing and also provided structure-activity relationship of this series. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.06.035

文献信息

• Biological activity evaluation and molecular docking study of chromone derivatives as cyclooxygenase-2 inhibitors
  作者：Chirattikan Maicheen、Narumol Phosrithong、Jiraporn Ungwitayatorn

  DOI：10.1007/s00044-017-1786-0

  日期：2017.3

  A series of chromone derivatives have been evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. The four most potent compounds, 48, 41, 39, and 35 displayed IC50 values of 3.30, 6.86, 7.36 and 7.46 µM, respectively. Compounds 35 and 38 showed higher selectivity for COX-2 (selectivity index, SI = 7.48 and 5.46, respectively) than celecoxib (SI = 4.17 in the same test) whereas compound 39 showed

  一系列色酮衍生物已被评估为潜在的环氧合酶2（COX-2）抑制剂。四个最有效的化合物，48，41，39，和35显示的IC 50个分别3.30，6.86，7.36和7.46μM的值，。与塞来昔布（同一试验中SI = 4.17）相比，化合物35和38对COX-2的选择性更高（分别为SI = 7.48和5.46），而化合物39对塞来昔布的选择性更高（SI = 4.19）。化合物的分子体积35（312.84埃3）和38（314.18埃3）类似于塞来考昔（299.28埃3），但大于布洛芬（211.83埃3）。在结合能和结合方式的评价方面，对接结果与实验生物学数据非常吻合。化合物35，38和39对COX-2具有更高的结合亲和力比COX-1（间-9.77和-11.42千卡/摩尔结合能）（-6.28和-7.88千卡/摩尔之间的结合能量）。这三种色酮化合物在与塞来昔布相同的方向上也显示出活性构象。因此，该系列
• An efficient one-pot synthesis of flavones
  作者：Chin Fei Chee、Michael J.C. Buckle、Noorsaadah Abd. Rahman

  DOI：10.1016/j.tetlet.2011.04.022

  日期：2011.6

  Flavones were prepared using a one-pot procedure starting from the corresponding 2'-hydroxyacetophenones. The latter were treated with 3 equiv of aroyl chloride in wet K2CO3/acetone (1% w/w water) to afford a good yield of flavone and a smaller amount of 3-aroylflavone. Evidence was obtained that the reaction proceeds via a triketone intermediate. When the reactants were heated in 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and pyridine, the 3-aroylflavone was obtained exclusively. Use of a stoichiometric amount of aroyl chloride afforded only the corresponding flavone. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor
  作者：Jiraporn Ungwitayatorn、Chanpen Wiwat、Weerasak Samee、Patcharawee Nunthanavanit、Narumol Phosrithong

  DOI：10.1016/j.molstruc.2011.06.035

  日期：2011.8

  Novel chromone derivatives with a benzopyran-4-one scaffold have been prepared by the one-pot cyclization reaction. The in vitro inhibitory activity of these new compounds towards HIV-1 protease have been evaluated using stop time HPLC method as the preliminary screening. The most potent compound, 7,8-dihydroxy-2-(3'-trifluoromethyl phenyl)-3-(3 ''-trifluoromethylbenzoyl)chromone (32), showed IC50 = 0.34 mu M. The molecular docking study supported results from experimental activity testing and also provided structure-activity relationship of this series. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis, Topoisomerase I Inhibitory and Cytotoxic Activities of Chromone Derivatives
  作者：Chirattikan Maicheen、Jiraphun Jittikoon、Opa Vajragupta、Jiraporn Ungwitayatorn

  DOI：10.2174/1573406411309030003

  日期：2013.2.1

  A series of chromone derivatives were designed as potential topoisomerase I (Top I) inhibitors based on the docking simulation study. Sixteen synthesized compounds were evaluated for Top I inhibitory activity and some compounds were further tested for in vitro cytotoxic activity. The most potent inhibitor, chromone 11b showed greater inhibitory activity (IC50 = 1.46 μM) than the known Top I inhibitors, i.e., camptothecin, fisetin and morin, but inactive against breast cancer cell (MCF-7), oral cavity cancer cell (KB) and small cell lung cancer (NCI-H187). Chromone 11c, another potent inhibitor (IC50 = 6.16 μM), exhibited cytotoxic activity against KB (IC50 = 73.32 μM) and NCI-H187 (IC50 = 36.79 μM).

  根据对接模拟研究，设计了一系列铬酮衍生物作为潜在的拓扑异构酶 I（Top I）抑制剂。对合成的 16 个化合物进行了拓扑异构酶 I 抑制活性评估，并进一步对一些化合物进行了体外细胞毒性测试。最有效的抑制剂色酮 11b 比已知的 Top I 抑制剂喜树碱、鱼藤素和吗啉具有更强的抑制活性（IC50 = 1.46 μM），但对乳腺癌细胞（MCF-7）、口腔癌细胞（KB）和小细胞肺癌（NCI-H187）没有活性。Chromone 11c 是另一种强效抑制剂（IC50 = 6.16 μM），对 KB（IC50 = 73.32 μM）和 NCI-H187 （IC50 = 36.79 μM）具有细胞毒性活性。