[4-[(1E,6E)-7-(4-benzoyloxy-3-methoxyphenyl)-4-(2-hydroxyethyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] benzoate | 1220971-43-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: [4-[(1E,6E)-7-(4-benzoyloxy-3-methoxyphenyl)-4-(2-hydroxyethyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] benzoate
• CAS: 1220971-43-6
• 化学式: C₃₇H₃₂O₉
• 分子量: 620.656
• InChiKey: CHBMBFALTSCLOS-HBKJEHTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [4-[(1E,6E)-7-(4-benzoyloxy-3-methoxyphenyl)-4-(2-hydroxyethyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] benzoate 、 (2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]-5-(4-nitrophenoxy)-5-oxopentanoic acid 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis, antibacterial and antiviral properties of curcumin bioconjugates bearing dipeptide, fatty acids and folic acid

  摘要：

  Curcumin bioconjugates, viz. di-O-tryptophanylphenylalanine curcumin (2), di-O-decanoyl curcumin (3), di-O-pamitoyl curcumin (4), di-O-bis-(gamma,gamma)folyl curcumin (6), C-4-ethyl-O-gamma-folyl curcumin (8) and 4-O-ethyl-O-gamma-folyl curcumin (10) have been synthesized and tested for their antibacterial and antiviral activities. The conjugates 2, 3, 4, 6 and 8 have shown very promising antibacterial activity with MIC ranging between 0.09 and 0.67 mu M against Gram-positive cocci and Gram-negative bacilli. Further, the conjugates 2, 3, 6, 8 and 10 have been screened for their antiviral activities against HSV, VSV, FIPV, PIV-3, RSV and FHV and the molecules 2 and 3 have shown good results with EC50 0.011 mu M and 0.029 mu M against VSV and FIPV/FHV, respectively. However, the molecules did not show expected results against HIV-1 IIIB and ROD strains in MTT assay. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.002
• 作为产物：
  描述：

  di-O-benzoyl curcumin 、 2-氯乙醇 在 sodium ethanolate 、 吡啶 作用下， 以 乙醇 为溶剂， 反应 6.83h， 以183 mg的产率得到[4-[(1E,6E)-7-(4-benzoyloxy-3-methoxyphenyl)-4-(2-hydroxyethyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] benzoate
  参考文献：
  名称：

  Synthesis, antibacterial and antiviral properties of curcumin bioconjugates bearing dipeptide, fatty acids and folic acid

  摘要：

  Curcumin bioconjugates, viz. di-O-tryptophanylphenylalanine curcumin (2), di-O-decanoyl curcumin (3), di-O-pamitoyl curcumin (4), di-O-bis-(gamma,gamma)folyl curcumin (6), C-4-ethyl-O-gamma-folyl curcumin (8) and 4-O-ethyl-O-gamma-folyl curcumin (10) have been synthesized and tested for their antibacterial and antiviral activities. The conjugates 2, 3, 4, 6 and 8 have shown very promising antibacterial activity with MIC ranging between 0.09 and 0.67 mu M against Gram-positive cocci and Gram-negative bacilli. Further, the conjugates 2, 3, 6, 8 and 10 have been screened for their antiviral activities against HSV, VSV, FIPV, PIV-3, RSV and FHV and the molecules 2 and 3 have shown good results with EC50 0.011 mu M and 0.029 mu M against VSV and FIPV/FHV, respectively. However, the molecules did not show expected results against HIV-1 IIIB and ROD strains in MTT assay. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.002

文献信息

• Synthesis, antibacterial and antiviral properties of curcumin bioconjugates bearing dipeptide, fatty acids and folic acid
  作者：Ramendra K. Singh、Diwakar Rai、Dipti Yadav、A. Bhargava、J. Balzarini、E. De Clercq

  DOI：10.1016/j.ejmech.2009.12.002

  日期：2010.3

  Curcumin bioconjugates, viz. di-O-tryptophanylphenylalanine curcumin (2), di-O-decanoyl curcumin (3), di-O-pamitoyl curcumin (4), di-O-bis-(gamma,gamma)folyl curcumin (6), C-4-ethyl-O-gamma-folyl curcumin (8) and 4-O-ethyl-O-gamma-folyl curcumin (10) have been synthesized and tested for their antibacterial and antiviral activities. The conjugates 2, 3, 4, 6 and 8 have shown very promising antibacterial activity with MIC ranging between 0.09 and 0.67 mu M against Gram-positive cocci and Gram-negative bacilli. Further, the conjugates 2, 3, 6, 8 and 10 have been screened for their antiviral activities against HSV, VSV, FIPV, PIV-3, RSV and FHV and the molecules 2 and 3 have shown good results with EC50 0.011 mu M and 0.029 mu M against VSV and FIPV/FHV, respectively. However, the molecules did not show expected results against HIV-1 IIIB and ROD strains in MTT assay. (C) 2009 Elsevier Masson SAS. All rights reserved.