7-(2-oxo-2-phenylethoxy)-2H-1-benzopyran-2-one | 68454-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(2-oxo-2-phenylethoxy)-2H-1-benzopyran-2-one
• 英文别名: 7-Phenacyloxy-cumarin；7-Phenacetyloxycumarin；7-(2-oxo-2-phenyl-ethoxy)-chromen-2-one；7-phenacyloxy-coumarin；7-(2-oxo-2-phenylethoxy)-2H-chromen-2-one；7-phenacyloxychromen-2-one
• CAS: 68454-19-3
• 化学式: C₁₇H₁₂O₄
• mdl: MFCD00415124
• 分子量: 280.28
• InChiKey: XFZPLDRMRZGQKD-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  504.3±50.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  7-(2-oxo-2-phenylethoxy)-2H-1-benzopyran-2-one 在 氢氧化钾 作用下， 反应 24.0h， 生成 3-phenyl-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Alkoxypsoralens, Novel Nonpeptide Blockers of Shaker-Type K⁺ Channels:  Synthesis and Photoreactivity

  摘要：

  A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus Laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8-Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.

  DOI：

  10.1021/jm981032o
• 作为产物：
  描述：

  7-羟基香豆素 、 alpha-氯乙酰苯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 7-(2-oxo-2-phenylethoxy)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Alkoxypsoralens, Novel Nonpeptide Blockers of Shaker-Type K⁺ Channels:  Synthesis and Photoreactivity

  摘要：

  A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus Laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8-Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.

  DOI：

  10.1021/jm981032o

文献信息

• .alpha.-methylene-.gamma.-butyrolactones: new inhibitors of platelet
  申请人：National Science Council

  公开号：US05646164A1

  公开（公告）日：1997-07-08

  The present inventors have discovered three classes of novel .alpha.-methylene-.gamma.-butyrolactones with excellent antiplatelet activity. As a result of intensive studies, it has been found that compounds represented by the formula I-III are potent inhibitors of platelet aggregation. ##STR1## For the formula I, R.sub.1 is a methyl, a phenyl group optionally substituted with one or two group selected from halide, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, phenyl, nitro, amino. For the formula II, R.sub.1 is a methyl, a phenyl group optionally substituted with one or two group selected from halide, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, phenyl, nitro, amino; R.sub.2 represents hydrogen, halide, (C.sub.1 -C.sub.4) alkyl, phenyl, nitro, amino; R.sub.3 represents hydrogen, halide, (C.sub.1 -C.sub.4) alkyl, phenyl, nitro, amino. For the formula III, R.sub.1 is a methyl, a phenyl group optionally substituted with one or two group selected from halide, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, phenyl, nitro, amino; R.sub.4 represents hydrogen, hydroxy, (C.sub.1 -C.sub.4) alkyl. The present invention also provides a cost-efficient method for the preparation of formula I-III. Formula I-III may be administered orally or parenterly with an inert diluent or with a pharmaceutically acceptable carrier in the treatment or the prevention of cardiovascular disease.

  目前的发明者发现了三类具有出色抗血小板活性的新型α-亚甲基-γ-丁酸内酯。经过深入研究发现，由I-III式表示的化合物是有效的血小板聚集抑制剂。对于式I，R.sub.1是一个甲基，一个苯基，可选择地取代为卤素、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)氧烷基、苯基、硝基、氨基中的一个或两个基团。对于式II，R.sub.1是一个甲基，一个苯基，可选择地取代为卤素、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)氧烷基、苯基、硝基、氨基中的一个或两个基团；R.sub.2代表氢、卤素、(C.sub.1 -C.sub.4)烷基、苯基、硝基、氨基；R.sub.3代表氢、卤素、(C.sub.1 -C.sub.4)烷基、苯基、硝基、氨基。对于式III，R.sub.1是一个甲基，一个苯基，可选择地取代为卤素、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)氧烷基、苯基、硝基、氨基中的一个或两个基团；R.sub.4代表氢、羟基、(C.sub.1 -C.sub.4)烷基。本发明还提供了一种成本效益高的制备I-III式的方法。I-III式可以通过口服或肌注与惰性稀释剂或药用载体一起使用，用于治疗或预防心血管疾病。
• Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent
  作者：Zhanwei Ma、Min Zhou、Lin Ma、Min Zhang

  DOI：10.1177/1747519820907244

  日期：2020.7

  acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare

  由伊顿试剂（五氧化二磷-甲磺酸）促进的 α-苯氧基酮的环脱水用于在温和条件下以中等至优异的产率制备 3-取代或 2,3-二取代的苯并呋喃。该方法提供了从容易获得的起始材料（如苯酚和 α-溴酮）中轻松获得苯并呋喃的途径。反应效率高，这归功于伊顿试剂良好的反应性和流动性。该反应可用于制备萘并呋喃香豆素、苯并噻吩和苯并吡喃。
• Synthesis and Evaluation of Coumarin .ALPHA.-Methylene-.GAMMA.-butyrolactones: A New Class of Platelet Aggregation Inhibitors.
  作者：Yeh-Long CHEN、Tai-Chi WANG、Shiu-Chuan LIANG、Che-Ming TENG、Cherng-Chyi TZENG

  DOI：10.1248/cpb.44.1591

  日期：——

  In a search for new inhibitors of platelet aggregation, certain coumarin-bearing α-methylene-γ-butyrolactones were synthesized and evaluated for inhibitory activity against thrombin (Thr)-, arachidonic acid (AA)-, collagen (Col)-, and platelet-activating factor (PAF)-induced aggregation in washed rabbit platelets. These compounds were efficiently synthesized from commercially available 7-hydroxycoumarin or its derivative. Among them, 7-[(2, 3, 4, 5-tetrahydro-4-methylene-5-oxo-2-phenyl-2-furanyl)methoxy]-2H-1-benzopyran-2-one (3d) showed the most potent inhibition of AA- and PAF- induced aggregation, with IC50 values of 3.65 and 16.36μM respectively.

  在寻找新的血小板聚集抑制剂的过程中，合成了某些含香豆素的α-亚甲基-γ-丁内酯，并评估其对洗涤兔血小板中由凝血酶（Thr）、花生四烯酸（AA）、胶原（Col）和血小板激活因子（PAF）诱导的聚集的抑制活性。这些化合物是从商业可得的7-羟基香豆素或其衍生物高效合成的。在这些化合物中，7-[（2, 3, 4, 5-四氢-4-亚甲基-5-氧代-2-苯基-2-呋喃基）甲氧基]-2H-1-苯并吡喃-2-酮（3d）显示出对AA和PAF诱导的聚集最强的抑制作用，其IC50值分别为3.65μM和16.36μM。
• Ray et al., Journal of the Chemical Society, 1935, p. 813,815
  作者：Ray et al.

  DOI：——

  日期：——
• Novel oxime-bearing coumarin derivatives act as potent Nrf2/ARE activators in vitro and in mouse model
  作者：Ken-Ming Chang、Huang-Hui Chen、Tai-Chi Wang、I-Li Chen、Yu-Tsen Chen、Shyh-Chyun Yang、Yeh-Long Chen、Hsin-Huei Chang、Chih-Hsiang Huang、Jang-Yang Chang、Chuan Shih、Ching-Chuan Kuo、Cherng-Chyi Tzeng

  DOI：10.1016/j.ejmech.2015.10.029

  日期：2015.12

  We have designed and synthesized certain novel oxime- and amide-bearing coumarin derivatives as nuclear factor erythroid 2 p45-related factor 2 (Nrf2) activators. The potency of these compounds was measured by antioxidant responsive element (ARE)-driven luciferase activity, level of Nrf2-related cytoprotective genes and proteins, and antioxidant activity. Among them, (Z)-3-(2-(hydroxyimino)-2-phenylethoxy)-2H-chromen-2-one (17a) was the most active, and more potent than the positive t-BHQ in the induction of ARE-driven luciferase activity. Exposure of HSC-3 cells to various concentrations of 17a strongly increased Nrf2 nuclear translocation and the expression level of Nrf2-mediated cytoprotective proteins in a concentration-dependent manner. HSC-3 cells pretreated with 17a significantly reduced t-BOOH-induced oxidative stress. In the animal experiment, Nrf2-mediated cytoprotective proteins, such as aldo-keto reductase 1 subunit C-1 (AKR1C1), glutathione reductase (GR), and heme oxygenase (HO-1), were obviously elevated in the liver of 17a-treated mice than that of control. These results suggested that novel oxime-bearing coumarin 17a is able to activate Nrf2/ARE pathway in vivo and are therefore seen as a promising candidate for further investigation. (C) 2015 Elsevier Masson SAS. All rights reserved.