6-hydroxy-4-methoxy-5-acetoacetylbenzofuran | 81490-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-hydroxy-4-methoxy-5-acetoacetylbenzofuran
• 英文别名: ω-Acetovisnaginone；1-(6-hydroxy-4-methoxy-benzofuran-5-yl)-butane-1,3-dione；1-(6-Hydroxy-4-methoxy-benzofuran-5-yl)-butan-1,3-dion；6-Hydroxy-4-methoxy-5-acetoacetyl-cumaron (= ω-Aceto-visnaginon)；ω-Aceto-visnaginon)；1-(6-Hydroxy-4-methoxy-1-benzofuran-5-yl)butane-1,3-dione
• CAS: 81490-34-8
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: RXEUHUKVQJTMSY-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  284.3±9.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-hydroxy-4-methoxy-5-acetoacetylbenzofuran 在 盐酸 、 乙醇 作用下， 生成 齿阿米素
  参考文献：
  名称：

  Clarke et al., Journal of the Chemical Society, 1948, p. 2260,2263

  摘要：

  DOI：
• 作为产物：
  描述：

  齿阿米素 在 氢氧化钾 、 乙醇 作用下， 生成 6-hydroxy-4-methoxy-5-acetoacetylbenzofuran
  参考文献：
  名称：

  Synthesis of potent antitumor and antiviral benzofuran derivatives

  摘要：

  A new series of potent antitumor and antiviral benzofuran derivatives was synthesized by the reaction of the furochromone-6-carboxaldehydes 1 and 2 with different heterocyclic amines to yield the benzofuran-5-carbonyl derivatives 4-11. The synthesized compounds 1, 3-11 were tested against twelve different human cancer cell lines and all of the compounds were more potent than the comparative standards. The HIV inhibitory activity of the tested compounds 1, 3-11 showed that they have higher potency than Atevirdine. Moreover, compound 6 was significantly potent with wider therapeutic index. The HIV-1 RT inhibitory activity showed that compounds 10, 11, 3 and 4 were notably potent but with lower therapeutic index than Atevirdine. The HCV NS3-4A protease inhibitor activity of the tested compounds revealed that they have weaker potency and less therapeutic index than VX-950, although compounds 1, 4, 9 and 6, respectively exhibited significant activity. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.069

文献信息

• Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: Design, synthesis and evaluation as potential anti-inflammatory agents
  作者：Ghaneya Sayed Hassan、Sahar Mahmoud Abou-Seri、Gehan Kamel、Mamdouh Moawad Ali

  DOI：10.1016/j.ejmech.2014.02.033

  日期：2014.4

  The most potent and selective COX-2 inhibitors – compounds 3c, 3d, 3e, 9c and 9d – were assessed for their anti-inflammatory activity and ulcerogenic liability in vivo. The 3-(pyridin-3-yl)pyrazole derivatives 3c and 3e exhibited the highest anti-inflammatory activity, that is equipotent to celecoxib. Furthermore, the tested compounds proved to have better gastric safety profile compared to celecoxib

  合成了具有苯并呋喃部分3a - e和9a - d的新系列塞来昔布类似物，并对其体外COX-1 / COX-2抑制活性进行了评估。评估了最有效和选择性最强的COX-2抑制剂-化合物3c，3d，3e，9c和9d的体内抗炎活性和致溃疡作用。3-（吡啶-3-基）吡唑衍生物3c和3e具有最高的抗炎活性，相当于塞来昔布。此外，与塞来昔布相比，被测化合物具有更好的胃安全性。特别地，相对于参考药物，化合物3e显示出致溃疡的可能性降低了约40％。最后，在COX-2活性位点和药物相似性研究中对新化合物进行了分子对接模拟，结果与所获得的药理生物学结果吻合良好。
• Hishmat; Miky; Saleh, Pharmazie, 1989, vol. 44, # 12, p. 823 - 825
  作者：Hishmat、Miky、Saleh

  DOI：——

  日期：——
• Hismat, Orchidee H.; Zohair, Madiha M. Y.; Soliman, Fekria M. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 11, p. 1001 - 1003
  作者：Hismat, Orchidee H.、Zohair, Madiha M. Y.、Soliman, Fekria M. A.

  DOI：——

  日期：——
• 624. Furanochromones. Part II. The synthesis of visnagin and related compounds
  作者：J. S. H. Davies、W. L. Norris

  DOI：10.1039/jr9500003195

  日期：——
• Mustafa,A. et al., Justus Liebigs Annalen der Chemie, 1965, vol. 684, p. 194 - 200
  作者：Mustafa,A. et al.

  DOI：——

  日期：——