4-hydroxy-6-methyl-3-[(2E,4E)-4-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)but-2-enoyl]-2H-pyran-2-one | 1084815-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-hydroxy-6-methyl-3-[(2E,4E)-4-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)but-2-enoyl]-2H-pyran-2-one
• 英文别名: 4-hydroxy-6-methyl-3-[(E,4E)-4-(1,3,3-trimethylindolin-2-ylidene)but-2-enoyl]pyran-2-one；4-hydroxy-6-methyl-3-[(E,4E)-4-(1,3,3-trimethylindol-2-ylidene)but-2-enoyl]pyran-2-one
• CAS: 1084815-88-2
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: BXUIKZAMCHNJEM-PFMZDYLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-methyl-2-oxo-3-[(2E,4E)-4-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)but-2-enoyl]-2H-pyran-4-yl difluoridoborate 在 水 、 sodium carbonate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以76%的产率得到4-hydroxy-6-methyl-3-[(2E,4E)-4-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)but-2-enoyl]-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