7,7'-dimethoxy-2H,2'H-3,3'-bichromene-2,2'-dione | 115230-76-7

• 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: 7,7'-dimethoxy-2H,2'H-3,3'-bichromene-2,2'-dione
• 英文别名: 7,7’-dimethoxy-3,3’-biscoumarin；7,7'-dimethoxy-[3,3']bichromenyl-2,2'-dione；7,7'-Dimethoxy-3,3'-bicumarinyl；7,7'-Dimethoxy-2H,2'H-[3,3'-bi-1-benzopyran]-2,2'-dione；7-methoxy-3-(7-methoxy-2-oxochromen-3-yl)chromen-2-one
• CAS: 115230-76-7
• 化学式: C₂₀H₁₄O₆
• 分子量: 350.328
• InChiKey: FCWUDEWOPNJZGG-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  579.4±50.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-bromo-7-methoxycoumarin 在 indium 、 palladium diacetate 、 三苯基膦 、 lithium chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 96.0h， 以13%的产率得到7,7'-dimethoxy-2H,2'H-3,3'-bichromene-2,2'-dione
  参考文献：
  名称：

  Evaluation of synthesized coumarin derivatives on aromatase inhibitory activity

  摘要：

  In women across the world, the most common type of cancer is breast cancer. Among medical treatments, endocrine therapy based on aromatase inhibitors (AI) is expected to be effective against not only post-menopausal but also pre-menopausal breast cancer. In this study, we examined the structure-activity relationship between the aromatase inhibitory effects of 7-diethylaminocoumarin derivatives with a substituent at position 3 and coumarin derivatives with a substituent at position 7. Consequently, we found that 7-(pyridin-3-yl) coumarin (IC50 values 30.3 nM) and 7,7'-diethylamino-3,3'-biscoumarin (28.7 nM) are the most potent inhibitors of aromatase. These inhibitors were found to be comparable to the existing CYP19 inhibitor exemestane (42.5 nM). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.01.062

文献信息

• Microwave assisted one pot synthesis of 7-substituted 2-(2-oxo-2H-chromen-3-yl)acetic acids as precursors of new anti-tumour compounds
  作者：Silvia Kováčová、Lucia Kováčiková、Margita Lácová、Andrej Boháč、Marta Sališová

  DOI：10.2478/s11696-010-0059-x

  日期：2010.1.1

  lactonisation as one pot syntheses of 2-(2-oxo-2H-chromen-3-yl)acetic acids VIIa-Xa has been studied. The required acids VIIa-Xa were prepared as precursors of recently discovered compounds possessing antineoplastic activities. Syntheses of VIIa-Xa were carried out using para substituted 2-hydroxybenzaldehydes II-VI, succinic acid anhydride, sodium succinate under thermal or microwave conditions. Significant

  已经研究了珀金（Perkin）缩合和随后的分子内内酯化，作为2-（2-氧代-2 H-铬-3-基）乙酸VIIa-Xa的一锅合成。所需的酸VIIa-Xa被制备为最近发现的具有抗肿瘤活性的化合物的前体。使用对位取代的2-羟基苯甲醛II-VI，琥珀酸酐，琥珀酸钠在热或微波条件下进行VIIa-Xa的合成。观察到微波辐照的反应时间显着缩短（18-50分钟，而不是加热1.5-5小时）。微波辅助反应进行得更加顺利，从而可以提高所需产物VIIa-Xa的产率（31–61％），相比之下，在经典的热条件下，例如IXa为21.8％（Hurenkamp等，2007）。副产物七个反应分离和确定为2 ħ，2' ħ -3,3'- bichromene -2,2'-二酮的VIIb-XB和（ë）-3-（2-羟基苯乙烯基）-2 ħ -色烯-2-ones VIIc-IXc。
• A New Gold-Catalyzed Domino Cyclization and Oxidative Coupling Reaction
  作者：Hermann A. Wegner、Sebastian Ahles、Markus Neuburger

  DOI：10.1002/chem.200801848

  日期：——
• Evaluation of synthesized coumarin derivatives on aromatase inhibitory activity
  作者：Yuki Yamaguchi、Naozumi Nishizono、Daisuke Kobayashi、Teruki Yoshimura、Keiji Wada、Kazuaki Oda

  DOI：10.1016/j.bmcl.2017.01.062

  日期：2017.6

  In women across the world, the most common type of cancer is breast cancer. Among medical treatments, endocrine therapy based on aromatase inhibitors (AI) is expected to be effective against not only post-menopausal but also pre-menopausal breast cancer. In this study, we examined the structure-activity relationship between the aromatase inhibitory effects of 7-diethylaminocoumarin derivatives with a substituent at position 3 and coumarin derivatives with a substituent at position 7. Consequently, we found that 7-(pyridin-3-yl) coumarin (IC50 values 30.3 nM) and 7,7'-diethylamino-3,3'-biscoumarin (28.7 nM) are the most potent inhibitors of aromatase. These inhibitors were found to be comparable to the existing CYP19 inhibitor exemestane (42.5 nM). (C) 2017 Elsevier Ltd. All rights reserved.