(E)-1-(4-hydroxybenzofuran-5-yl)-3-(4-methoxyphenyl)prop-2-en-1-one | 77373-19-4

• 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
• 英文名称: (E)-1-(4-hydroxybenzofuran-5-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 2'-hydroxy-4-methoxyfurano<4'',5'': 3',4'>chalkone；2'-hydroxy-4-methoxyfurano(3',4'-4",5")chalcone；(E)-1-(4-hydroxy-1-benzofuran-5-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 77373-19-4；82427-67-6
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: WYTHYEAIGVSMRF-XBXARRHUSA-N

物化性质

• 沸点：
  392.3±34.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 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：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-hydroxybenzofuran-5-yl)-3-(4-methoxyphenyl)prop-2-en-1-one 在 selenium(IV) oxide 作用下， 以 异戊醇 为溶剂， 反应 8.0h， 以36 mg的产率得到4'-Methoxyfurano<4'',5'': 8,7>flavone
  参考文献：
  名称：

  Isopongaglabol 和 6-methoxyisopongaglabol，两种来自水杨树的新羟基呋喃黄酮

  摘要：

  摘要 Isopgaglabol 和 6-methoxyisopongaglabol，两种新的羟基呋喃黄酮，以及两种呋喃黄酮 5-甲氧基呋喃 (8,7-4",5") 黄酮和 5-甲氧基-3',4'-亚甲二氧基呋喃 (8,7-4")， 5″)黄酮、两种简单黄酮、去甲氧基卡努金和非瑟酮四甲醚、一种色烯黄酮、卵色烯B、两种三萜、cycloart-23-ene-3β,25-二醇和弗里德林，以及β-谷甾醇-β-d-葡萄糖苷来自水杨花的汽油和 CHCl 3 提取物。异蓬加拉波和 6-甲氧基异蓬加拉波的结构已确定为 4'-羟基呋喃 (8,7-4",5") 黄酮和 4'-羟基-6-甲氧基呋喃 (8,7-4",5") 黄酮，分别是根据光谱证据和合成证实的。

  DOI：

  10.1016/0031-9422(82)83183-x
• 作为产物：
  描述：

  lanceolatin B 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 29.08h， 生成 (E)-1-(4-hydroxybenzofuran-5-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Isopongaglabol 和 6-methoxyisopongaglabol，两种来自水杨树的新羟基呋喃黄酮

  摘要：

  摘要 Isopgaglabol 和 6-methoxyisopongaglabol，两种新的羟基呋喃黄酮，以及两种呋喃黄酮 5-甲氧基呋喃 (8,7-4",5") 黄酮和 5-甲氧基-3',4'-亚甲二氧基呋喃 (8,7-4")， 5″)黄酮、两种简单黄酮、去甲氧基卡努金和非瑟酮四甲醚、一种色烯黄酮、卵色烯B、两种三萜、cycloart-23-ene-3β,25-二醇和弗里德林，以及β-谷甾醇-β-d-葡萄糖苷来自水杨花的汽油和 CHCl 3 提取物。异蓬加拉波和 6-甲氧基异蓬加拉波的结构已确定为 4'-羟基呋喃 (8,7-4",5") 黄酮和 4'-羟基-6-甲氧基呋喃 (8,7-4",5") 黄酮，分别是根据光谱证据和合成证实的。

  DOI：

  10.1016/0031-9422(82)83183-x

文献信息

• Synthesis of antihyperglycemic, α-glucosidase inhibitory, and DPPH free radical scavenging furanochalcones
  作者：R. Ranga Rao、Ashok K. Tiwari、P. Prabhakar Reddy、K. Suresh Babu、G. Suresh、A. Zehra Ali、K. Madhusudana、Sachin B. Agawane、Preethi Badrinarayan、G. Narahari Sastry、J. Madhusudana Rao

  DOI：10.1007/s00044-011-9583-7

  日期：2012.6

  A series of furanochalcone derivatives have been designed and synthesized. Molecular modeling studies were carried out to probe into the mechanism of binding of chalcone inhibitors and understand the structure-activity relationship to identify the contribution of scaffolds and groups in the synthesized analogs to biological activity. The three-dimensional model of alpha-glucosidase was constructed based on the crystal structure family 31 alpha-glycosidase (PDB 1XSI) using Modeller9v5. Docking of the inhibitors on the built homology model revealed interactions in the active site region mostly with Asp 252, Tyr254, Gln523, and Arg571. 2D-QSAR models were generated with CODESSA using Heuristic method. The best predictive model was generated using three descriptors that gave a correlation co-efficient (r (2)) 0.9886 and cross-validate (r (2)) 0.9338. The synthesized compounds were screened against the alpha-glucosidase inhibition and DPPH radical scavenging properties. All the synthetic compounds displayed varying degrees of alpha-glucosidase inhibitory and DPPH scavenging activities. Compound 8c was found most potent alpha-glucosidase inhibitor though; it could not display DPPH scavenging activity. When tested in vivo for antihyperglycemic activity in starch-loaded Wistar rats, 8c was equally effective in reducing time-dependent hyperglycemia as to the standard drug, Acarbose. Compound 8c may serve as an interesting compound for the development of therapeutics targeted against diet-induced hyperglycemia in diabetes.
• Krishnamurti, M.; Parthasarathi, J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 9, p. 816 - 817
  作者：Krishnamurti, M.、Parthasarathi, J.

  DOI：——

  日期：——
• Isopongaglabol and 6-methoxyisopongaglabol, two new hydroxyfuranoflavones from Pongamia glabra
  作者：Sunil K. Talapatra、Asok K. Mallik、Bani Talapatra

  DOI：10.1016/0031-9422(82)83183-x

  日期：——

  6-methoxyisopongaglabol, two new hydroxyfuranoflavones, together with two furanoflavones 5-methoxyfurano(8,7-4″,5″)flavone and 5-methoxy-3′,4′-methylenedioxyfurano(8,7-4″,5″)flavone, two simple flavones, desmethoxykanugin and fisetin tetramethyl ether, a chromenoflavanone, ovalichromene B, two triterpenes, cycloart-23-ene-3β,25-diol and friedelin, and β-sitosterol-β- d -glucoside were isolated from the petrol and

  摘要 Isopgaglabol 和 6-methoxyisopongaglabol，两种新的羟基呋喃黄酮，以及两种呋喃黄酮 5-甲氧基呋喃 (8,7-4",5") 黄酮和 5-甲氧基-3',4'-亚甲二氧基呋喃 (8,7-4")， 5″)黄酮、两种简单黄酮、去甲氧基卡努金和非瑟酮四甲醚、一种色烯黄酮、卵色烯B、两种三萜、cycloart-23-ene-3β,25-二醇和弗里德林，以及β-谷甾醇-β-d-葡萄糖苷来自水杨花的汽油和 CHCl 3 提取物。异蓬加拉波和 6-甲氧基异蓬加拉波的结构已确定为 4'-羟基呋喃 (8,7-4",5") 黄酮和 4'-羟基-6-甲氧基呋喃 (8,7-4",5") 黄酮，分别是根据光谱证据和合成证实的。