Benzoic acid 5-(2-chloro-5-methyl-imidazo[1,5-b]pyridazin-7-yl)-pentyl ester | 152533-89-6

• 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: Benzoic acid 5-(2-chloro-5-methyl-imidazo[1,5-b]pyridazin-7-yl)-pentyl ester
• 英文别名: 5-(2-Chloro-5-methyl-imidazo[1,5-b]pyridazin-7-yl)pentyl benzoate；5-(2-chloro-5-methylimidazo[1,5-b]pyridazin-7-yl)pentyl benzoate
• CAS: 152533-89-6
• 化学式: C₁₉H₂₀ClN₃O₂
• 分子量: 357.84
• InChiKey: VAQJZQNQAXFGQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzoic acid 5-(2-chloro-5-methyl-imidazo[1,5-b]pyridazin-7-yl)-pentyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 240.0h， 以87%的产率得到5-(2-Chloro-5-methylimidazo[1,5-b]pyridazin-7-yl)pentan-1-ol
  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：

  N-1-(2,3-dihydro-3-oxopyridazin-6-yl)ethylamine hydrochloride 在 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 27.0h， 生成 Benzoic acid 5-(2-chloro-5-methyl-imidazo[1,5-b]pyridazin-7-yl)-pentyl ester
  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.