ethyl 2-amino-7-hydroxy-4-phenyl-4H-benzopyran-3-carboxylate | 111861-30-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: ethyl 2-amino-7-hydroxy-4-phenyl-4H-benzopyran-3-carboxylate
• 英文别名: 2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylic acid ethyl ester；ethyl 2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylate
• CAS: 111861-30-4
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: QSYXPLNCWYFNQS-UHFFFAOYSA-N

物化性质

• 熔点：
  227 °C
• 沸点：
  492.3±45.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)
• 溶解度：
  <0.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  反式-α-氰基肉桂酸乙酯 、 间苯二酚 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以65%的产率得到ethyl 2-amino-7-hydroxy-4-phenyl-4H-benzopyran-3-carboxylate
  参考文献：
  名称：

  SYNTHESIS OF NEW CONDENSED 2-AMINO-4H-PYRAN-3-CARBONITRILES AND OF 2-AMINOQUINOLINE-3-CARBONITRILES

  摘要：

  DOI：

  10.1080/00304949909458324

文献信息

• Elagamey, Abdel Ghani A.; Sawllim, Salah Z.; El-Taweel, Fathy M.A., Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 7, p. 1534 - 1538
  作者：Elagamey, Abdel Ghani A.、Sawllim, Salah Z.、El-Taweel, Fathy M.A.、Elnagdi, Mohamed H.

  DOI：——

  日期：——
• Optimisation of estrogen receptor subtype-selectivity of a 4-Aryl-4H-chromene scaffold previously identified by virtual screening
  作者：Miriam Carr、Andrew J.S. Knox、Daniel K. Nevin、Niamh O'Boyle、Shu Wang、Billy Egan、Thomas McCabe、Brendan Twamley、Daniela M. Zisterer、David G. Lloyd、Mary J. Meegan

  DOI：10.1016/j.bmc.2019.115261

  日期：2020.3

  4-Aryl-4H-Chromene derivatives have been previously shown to exhibit anti-proliferative, apoptotic and anti-angiogenic activity in a variety of tumor models in vitro and in vivo generally via activation of caspases through inhibition of tubulin polymerisation. We have previously identified by Virtual Screening (VS) a 4-aryl-4H-chromene scaffold, of which two examples were shown to bind Estrogen Receptor alpha and beta with low nanomolar affinity and <20-fold selectivity for alpha over beta and low micromolar anti-proliferative activity in the MCF-7 cell line. Thus, using the 4-aryl-4H-chromene scaffold as a starting point, a series of compounds with a range of basic arylethers at C-4 and modifications at the C3-ester substituent of the benzopyran ring were synthesised, producing some potent ER antagonists in the MCF-7 cell line which were highly selective for ERa (compound 35; 350-fold selectivity) or ER beta (compound 42; 170-fold selectivity).
• Synthesis, characterization, and antibacterial evaluation of new alkyl 2-amino-4-aryl-4H-chromene-3-carboxylates
  作者：Sedighe Gholipour、Abolghasem Davoodnia、Mahboobeh Nakhaei-Moghaddam

  DOI：10.1007/s10593-015-1779-1

  日期：2015.9

  A series of alkyl 2-amino-4-aryl-4H-chromene-3-carboxylates was synthesized by an efficient, solvent-free one-pot three-component cyclocondensation of resorcinol, aromatic aldehydes, and ethyl or methyl cyanoacetate using sodium carbonate as catalyst. The present methodology offers several advantages, such as a simple procedure with ease of handling, short reaction time, high yields, and the absence of any volatile and hazardous organic solvents. The products were characterized on the basis of IR, H-1 NMR, and C-13 NMR spectral and microanalytical data and evaluated for their antibacterial activity against Gram-positive bacteria (Staphylococcus epidermidis and Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli) using paper disc diffusion technique.
• Radwan, Shaban M.; Bakhite, Etify A.; El-Dean, Adel M. Kamal, Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 101, # 1-4, p. 207 - 212
  作者：Radwan, Shaban M.、Bakhite, Etify A.、El-Dean, Adel M. Kamal

  DOI：——

  日期：——
• Klokol, G.V.; Sharanina, L.G.; Nesterov, V.N., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 369 - 377
  作者：Klokol, G.V.、Sharanina, L.G.、Nesterov, V.N.、Shklover, V.E.、Sharanin, Yu.A.、Struchkov, Yu.T.

  DOI：——

  日期：——