3-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}-6-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-4-hydroxy-2H-pyran-2-one | 1084815-99-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}-6-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-4-hydroxy-2H-pyran-2-one
• 英文别名: 6-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-3-[(E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl]-4-hydroxypyran-2-one
• CAS: 1084815-99-5
• 化学式: C₂₆H₂₆N₂O₄
• 分子量: 430.503
• InChiKey: VBQIGZXKOUQUAG-KAVGSWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}-6-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-2-oxo-2H-pyran-4-yl difluoridoborate 在 水 、 sodium carbonate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以72%的产率得到3-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}-6-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-4-hydroxy-2H-pyran-2-one
  参考文献：
  名称：

  Discovery of 3-acetyl-4-hydroxy-2-pyranone derivatives and their difluoridoborate complexes as a novel class of HIV-1 integrase Inhibitors

  摘要：

  HIV-1 integrase (IN) has emerged as an important therapeutic target for anti-HIV drug development. Its uniqueness to the virus and its critical role in the viral life cycle makes IN suitable for selective inhibition. The recent approval of Raltegravir (MK-0518) has created a surge in interest and great optimism in the field. In our ongoing IN drug design research, we herein report the discovery of substituted analogs of 3-acetyl-4-hydroxy-2-pyranones and their difluoridoborate complexes as novel IN inhibitors. In many of these compounds, complexation with boron difluoride increased the potency and selectivity of IN inhibition. Compound 9 was most active with an IC50 value of 9 mu M and 3 mu M for 3'-processing and strand transfer inhibition, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.067

文献信息

• Synthesis and reactions of dehydracetic acid difluoroborane complex
  作者：A. V. Manaev、K. V. Tambov、V. F. Traven’

  DOI：10.1134/s107042800807018x

  日期：2008.7

  Dehydracetic acid difluoroborane complex, 3-acetyl-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate, was synthesized and characterized. The complex was involved into condensation reactions at the acetyl group with various aromatic and heterocyclic aldehydes, and with the 4-dimethylaminobenzaldehyde it reacted also at the methyl group in the position 6.