4-(2-oxopropoxy)-2H-1-benzopyran-2-one | 18504-28-4

• 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: 4-(2-oxopropoxy)-2H-1-benzopyran-2-one
• 英文别名: 4-(2-oxopropoxy)chromen-2-one
• CAS: 18504-28-4
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: FLRCUUCDKBHADB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  4-(2-oxopropoxy)-2H-1-benzopyran-2-one 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以71%的产率得到(E)-4-[2-(hydroxyimino)propoxy]-2H-chromen-2-one
  参考文献：
  名称：

  Novel oxime-bearing coumarin derivatives act as potent Nrf2/ARE activators in vitro and in mouse model

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.10.029
• 作为产物：
  描述：

  华法林杂质 、 一氯丙酮 在 Amberlite IRA-400(Cl^(1-)) 作用下， 反应 18.0h， 以95%的产率得到4-(2-oxopropoxy)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Salunkhe, Deepak; Jagdale, Mansingrao; Mane, Ramchandra, Acta Chimica Hungarica, 1987, vol. 124, # 3, p. 411 - 412

  摘要：

  DOI：

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 Coumarin Derivatives as Inhibitors of Platelet Aggregation
  作者：Yeh-Long Chen、Tai-Chi Wang、Kuan-Han Lee、Cherng-Chyi Tzeng、Ya-Ling Chang、Che-Ming Teng

  DOI：10.1002/hlca.19960790308

  日期：1996.5.8

  In a search for the inhibitors of platelet aggregation, certain coumarin derivatives were synthesized and evaluated for antiplatelet activity against thrombin(Thr)-, arachidonic acid(AA)-, collagen(Col)-, and platelet-activating-factor(PAF)-induced aggregation in washed rabbit platelets. These compounds were synthesized from 4-hydroxycoumarin (1) or naphthalen-1-ol via alkylation and Reformatsky-type

  在寻找血小板聚集抑制剂时，合成了某些香豆素衍生物并评估了其对凝血酶（Thr）-，花生四烯酸（AA）-，胶原蛋白（Col）-和血小板活化因子（PAF）-的抗血小板活性。在洗涤的兔血小板中诱导聚集。这些化合物是由4-羟基香豆素（1）或萘-1-醇经烷基化和Reformatsky型缩合反应合成的（图1-3）。其中，显示了4-[（（2,3,4,5-四氢-4-亚甲基-5-氧代-2-苯基呋喃-2-基）甲氧基] -2 H -1-苯并吡喃-2-酮（6b）IC 50对AA和PAF诱导的聚集产生有效的抗血小板作用值分别为8.21和103.67m̈M（见表1和2）。通过在内酯环的2-苯基上引入适当的取代基，可以进一步提高6b对PAF诱导的聚集的抗血小板效力。
• Regio and diastereoselective synthesis of functionalized 2,3-dihydrofuro[3,2-c]coumarins via a one-pot three-component reaction
  作者：Elisa Altieri、Massimiliano Cordaro、Giovanni Grassi、Francesco Risitano、Angela Scala

  DOI：10.1016/j.tet.2010.10.023

  日期：2010.12

  An efficient and straightforward synthesis of furo[3 2-c]coumarins via the one-pot three-component condensation of aromatic aldehydes 4-hydroxycoumarin and alpha-chloroketones in refluxing n-propanol is described Pyridine or a mixture of AcOH and AcONH4 was used as a basic catalyst (C) 2010 Elsevier Ltd All rights reserved
• SALUNKHE, DEEPAK;JAGDALE, MANSINGRAO;MANE, RAMCHANDRA;SALUNKHE, MANIKRAO, ACTA CHIM. HUNG., 124,(1987) N 3, 411-412
  作者：SALUNKHE, DEEPAK、JAGDALE, MANSINGRAO、MANE, RAMCHANDRA、SALUNKHE, MANIKRAO

  DOI：——

  日期：——
• US5646164A
  申请人：——

  公开号：US5646164A

  公开（公告）日：1997-07-08