1-(6-羟基-4-甲氧基-苯并呋喃-5-基)-3-(4-甲氧基-苯基)-丙烯酮 | 54437-45-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1-(6-羟基-4-甲氧基-苯并呋喃-5-基)-3-(4-甲氧基-苯基)-丙烯酮
• 英文名称: 1-(6-hydroxy-4-methoxy-benzofuran-5-yl)-3-(4-methoxy-phenyl)-propenone
• 英文别名: 1-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 54437-45-5
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: DBLOLWFRDVWUCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.9
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(6-羟基-4-甲氧基-苯并呋喃-5-基)-3-(4-甲氧基-苯基)-丙烯酮 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以98%的产率得到1-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)-3-(4-methoxyphenyl)prop-2-ene-1-thione
  参考文献：
  名称：

  Thionation of Chalcone and Aurone Derivatives by Lawesson's Reagent

  摘要：

  The reaction of Lawesson's reagent (LR 5) with chalcones (4a-h) and aurones (12a-h) proceeds in refluxing toluene to give the respective benzofuranylprop-2-en-1-thiones (8a-h) and benzodifuran-3-thiones (13a-h). Correct elemental analyses and spectroscopic data were obtained for the new compounds.

  DOI：

  10.1080/10426507.2012.704457
• 作为产物：
  描述：

  齿阿米素 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 25.0h， 生成 1-(6-羟基-4-甲氧基-苯并呋喃-5-基)-3-(4-甲氧基-苯基)-丙烯酮
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of novel semi-synthetic flavonoids as antiproliferative agents

  摘要：

  Various flavonoid scaffold based derivatives viz furochalcones (3a-e, 6a-d and 9a-d), furoflavones (10a-d, 11a-d,12a-d,18a&b), flavones (21a-d), furoaurones (13a,b,14a-d and 15a-d) and 7-styrylfurochromones (22a-d and 25a-e) were designed and synthesized. The novel compounds were evaluated for their anti-proliferative activity against a panel of 60 cancer cell lines comprising 9 types of tumors. Ten compounds belonging to the major subgroups of flavonoids viz furochalcones (3a, 3d, 6b, 9a and 9b), furoflavones (12a and 12c), furoaurones (15d), styrylfurochromones (25b and 25e) showed very promising activity. These active compounds were also evaluated in vitro as kinase inhibitors against CDK2/cyclin E1, CDK4/cyclin D1 and GSK-3 beta and the best inhibition was displayed against GSK-3 beta with the allylfurochalcone derivative 9b exhibiting 80% decrease in GSK-3 beta catalytic activity. On the other hand, the styrylfurochromone 25e interestingly showed a 13% enhancement of GSK-3 beta catalytic power and a 12% reduction in CDK4/cyclin D1 activity. Finally, the in vivo anti-tumor activity of 25e was evaluated against breast cancer induced in mice. The results showed a profound anti-tumor effect of 25e that accompanies a significant increase and decrease in the levels of GSK-3 beta and cyclin D1, respectively. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.007

文献信息

• Benzofuran–Morpholinomethyl–Pyrazoline Hybrids as a New Class of Vasorelaxant Agents: Synthesis and Quantitative Structure–Activity Relationship Study
  作者：Ghaneya Sayed Hassan、Doaa Ezzat Abdel Rahman、Dalia Osama Saleh、Gehad Abdel Raheem Abdel Jaleel

  DOI：10.1248/cpb.c14-00572

  日期：——

  The benzofuran–morpholinomethyl–pyrazoline hybrids 4a–e, 5a–e and 6a–j were synthesized via reaction of α,β-unsaturated carbonyl compounds 3a–e with hydrazine hydrate, semicarbazide or thiosemicarbazide. Applying the Mannich reaction to 5-(5-aryl-4,5-dihydro-1H-pyrazol-3-yl)-4-methoxybenzofuran-6-ols 7a–e with morpholine hydrochloride and paraformaldehyde afforded positional isomeric 7-morpholinomethyl derivatives 4a–e and N-morpholinomethyl derivatives 8a–e. All the synthesized compounds showed significant vasodilatation properties in isolated thoracic aortic rings of rats precontracted using the standard norepinephrine hydrochloride technique. Compounds 3d, 3e, 5a–c, 6b, 6c, 6f, 6h and 6i exhibited activity (IC50 0.3185–0.4577 mM) superior to that of prazocin (IC50 0.487 mM), while 5d, 6j and 8c showed comparable activity (IC50 0.4789–0.4951 mM). The quantitative structure–activity relationship study revealed a correlation between the observed vasorelaxant activities of the newly synthesized compounds and their different physicochemical parameters, especially solubility, in addition to structure connectivity and energetic quantities calculated from stored three dimensional (3D) conformations. Absorption, distribution, metabolism and elimination (ADME) evaluation showed good agreement with the biological results obtained.

  苯并呋喃-吗啉甲基吡唑啉杂化物 4a-e、5a-e 和 6a-j 是通过 α、β-不饱和羰基化合物 3a-e 与肼水合物、半肼或硫代氨基肼反应合成的。将 5-(5-芳基-4,5-二氢-1H-吡唑-3-基)-4-甲氧基苯并呋喃-6-醇 7a-e 与盐酸吗啉和多聚甲醛进行曼尼希反应，可得到位置异构的 7-吗啉甲基衍生物 4a-e 和 N-吗啉甲基衍生物 8a-e。在使用标准盐酸去甲肾上腺素技术预收缩大鼠离体胸主动脉环时，所有合成化合物都显示出明显的血管扩张特性。化合物 3d、3e、5a-c、6b、6c、6f、6h 和 6i 的活性（IC50 0.3185-0.4577 mM）优于普拉佐辛（IC50 0.487 mM），而 5d、6j 和 8c 的活性（IC50 0.4789-0.4951 mM）相当。定量结构-活性关系研究表明，新合成化合物的血管舒张活性与其不同的理化参数（尤其是溶解度）之间存在相关性，此外，根据储存的三维构象计算出的结构连接性和能量量也存在相关性。吸收、分布、代谢和消除（ADME）评估结果显示，新合成的化合物与所获得的生物学结果非常吻合。
• Aziz,G. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1976, vol. 14, p. 286 - 291
  作者：Aziz,G. et al.

  DOI：——

  日期：——