3-[(2E)-3-(5-bromo-2-methoxyphenyl)prop-2-enoyl]-6-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-4-hydroxy-2H-pyran-2-one | 1084816-07-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-[(2E)-3-(5-bromo-2-methoxyphenyl)prop-2-enoyl]-6-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-4-hydroxy-2H-pyran-2-one
• 英文别名: 3-[(E)-3-(5-bromo-2-methoxy-phenyl)prop-2-enoyl]-6-[(E)-2-(4-dimethylaminophenyl)vinyl]-4-hydroxy-pyran-2-one；3-[(E)-3-(5-bromo-2-methoxyphenyl)prop-2-enoyl]-6-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-4-hydroxypyran-2-one
• CAS: 1084816-07-8
• 化学式: C₂₅H₂₂BrNO₅
• 分子量: 496.357
• InChiKey: AHGYLHPHMRGXIH-GNXRPPCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[(2E)-3-(5-bromo-2-methoxyphenyl)prop-2-enoyl]-6-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-2-oxo-2H-pyran-4-yl difluoridoborate 在 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以65%的产率得到3-[(2E)-3-(5-bromo-2-methoxyphenyl)prop-2-enoyl]-6-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-4-hydroxy-2H-pyran-2-one
  参考文献：
  名称：

  脱水乙酸二氟硼烷配合物的合成与反应

  摘要：

  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.

  DOI：

  10.1134/s107042800807018x

文献信息

• Discovery of 3-acetyl-4-hydroxy-2-pyranone derivatives and their difluoridoborate complexes as a novel class of HIV-1 integrase Inhibitors
  作者：Kavya Ramkumar、Konstantin V. Tambov、Rambabu Gundla、Alexandr V. Manaev、Vladimir Yarovenko、Valery F. Traven、Nouri Neamati

  DOI：10.1016/j.bmc.2008.08.067

  日期：2008.10

  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.