6-(1-benzoylamino-ethyl)-2H-pyridazin-3-one | 68219-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(1-benzoylamino-ethyl)-2H-pyridazin-3-one
• 英文别名: N-(1-(6-Oxo-1,6-dihydropyridazin-3-yl)ethyl)benzamide；N-[1-(6-oxo-1H-pyridazin-3-yl)ethyl]benzamide
• CAS: 68219-76-1
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: UELVVLPHGCBLEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  70.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(1-benzoylamino-ethyl)-2H-pyridazin-3-one 在 盐酸 、 三乙胺 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 7-(2-Chloro-5-methyl-imidazo[1,5-b]pyridazin-7-yl)-1-phenyl-heptan-1-one
  参考文献：
  名称：

  Synthesis and anti-HIV-1 activity of a series of imidazo[1,5-b]pyridazines

  摘要：

  A series of substituted imidazo[1,5-b]pyridazines have been prepared and tested for inhibitory activity against the reverse transcriptase of HIV-1 (RT) and their ability to inhibit the growth of infected MT-4 cells. Crystal data are reported on two compounds, 15c and 33. From the structure-activity relationships developed within this and other series, it is proposed that key features of the interaction with RT include hydrogen-bond acceptor and aromatic pi-orbital bonding with the imidazopyridazine nucleus and a benzoyl function separated from the heterocycle by a suitable spacer group. Exceptional activity against the reverse transcriptase of HIV-1 (IC50 = 0.65 nM) was obtained with a 2-imidazolyl-substituted derivative, 7-[2-(1H-imidazol-1-yl)-5-methylimidazo-[1,5-b]pyridazin-7-yl]-1-phenyl-1-heptanone (33) which is attributed to additional binding of the imidazole sp(2) nitrogen atom. A number of the compounds in this series also inhibit the replication of HIV-1 in vitro in MT-4 and C8166 cells at levels observed with the nucleoside AZT.

  DOI：

  10.1021/jm00076a005
• 作为产物：
  描述：

  5-Benzamido-4-oxohexansaeureethylester 在 溴 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 6-(1-benzoylamino-ethyl)-2H-pyridazin-3-one
  参考文献：
  名称：

  Synthesis and anti-HIV-1 activity of a series of imidazo[1,5-b]pyridazines

  摘要：

  A series of substituted imidazo[1,5-b]pyridazines have been prepared and tested for inhibitory activity against the reverse transcriptase of HIV-1 (RT) and their ability to inhibit the growth of infected MT-4 cells. Crystal data are reported on two compounds, 15c and 33. From the structure-activity relationships developed within this and other series, it is proposed that key features of the interaction with RT include hydrogen-bond acceptor and aromatic pi-orbital bonding with the imidazopyridazine nucleus and a benzoyl function separated from the heterocycle by a suitable spacer group. Exceptional activity against the reverse transcriptase of HIV-1 (IC50 = 0.65 nM) was obtained with a 2-imidazolyl-substituted derivative, 7-[2-(1H-imidazol-1-yl)-5-methylimidazo-[1,5-b]pyridazin-7-yl]-1-phenyl-1-heptanone (33) which is attributed to additional binding of the imidazole sp(2) nitrogen atom. A number of the compounds in this series also inhibit the replication of HIV-1 in vitro in MT-4 and C8166 cells at levels observed with the nucleoside AZT.

  DOI：

  10.1021/jm00076a005

文献信息

• Synthesis and anti-HIV-1 activity of a series of imidazo[1,5-b]pyridazines
  作者：David G. H. Livermore、Richard C. Bethell、Nicholas Cammack、Ashley P. Hancock、Michael M. Hann、Darren V. S. Green、R. Brian Lamont、Stewart A. Noble、David C. Orr

  DOI：10.1021/jm00076a005

  日期：1993.11

  A series of substituted imidazo[1,5-b]pyridazines have been prepared and tested for inhibitory activity against the reverse transcriptase of HIV-1 (RT) and their ability to inhibit the growth of infected MT-4 cells. Crystal data are reported on two compounds, 15c and 33. From the structure-activity relationships developed within this and other series, it is proposed that key features of the interaction with RT include hydrogen-bond acceptor and aromatic pi-orbital bonding with the imidazopyridazine nucleus and a benzoyl function separated from the heterocycle by a suitable spacer group. Exceptional activity against the reverse transcriptase of HIV-1 (IC50 = 0.65 nM) was obtained with a 2-imidazolyl-substituted derivative, 7-[2-(1H-imidazol-1-yl)-5-methylimidazo-[1,5-b]pyridazin-7-yl]-1-phenyl-1-heptanone (33) which is attributed to additional binding of the imidazole sp(2) nitrogen atom. A number of the compounds in this series also inhibit the replication of HIV-1 in vitro in MT-4 and C8166 cells at levels observed with the nucleoside AZT.