3-[(2E)-3-(4-bromo-2-thienyl)prop-2-enoyl]-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(2E)-3-(4-bromo-2-thienyl)prop-2-enoyl]-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate
• 英文别名: 5-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-3,3-difluoro-9-methyl-2,8-dioxa-4-oxonia-3-boranuidabicyclo[4.4.0]deca-1(6),4,9-trien-7-one
• 化学式: C₁₃H₈BBrF₂O₄S
• 分子量: 388.982
• InChiKey: CCMDLLPRXVSUGI-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[(2E)-3-(4-bromo-2-thienyl)prop-2-enoyl]-6-methyl-2-oxo-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3-[(2E)-3-(5-bromo-2-thienyl)prop-2-enoyl]-4-hydroxy-6-methyl-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
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 3-acetyl-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate 在 硫酸 、 溶剂黄146 作用下， 反应 0.5h， 以88%的产率得到3-[(2E)-3-(4-bromo-2-thienyl)prop-2-enoyl]-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate
  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

• 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.