N-(2,3-dihydro-3-oxopyridazin-6-yl)methylamine hydrochloride | 90175-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(2,3-dihydro-3-oxopyridazin-6-yl)methylamine hydrochloride
• 英文别名: 6-(Aminomethyl)pyridazin-3(2H)-one hydrochloride；3-(aminomethyl)-1H-pyridazin-6-one;hydrochloride
• CAS: 90175-93-2
• 化学式: C₅H₇N₃O*ClH
• 分子量: 161.591
• InChiKey: VJFFJRFVHXPNHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.35
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,3-dihydro-3-oxopyridazin-6-yl)methylamine 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 7-(2-Chloroimidazo[1,5-b]pyridazin-7-yl)-1-heptanone
  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：

  6-(benzoylamino-methyl)-4,5-dihydro-2H-pyridazin-3-one 在 盐酸 、 溴 、 溶剂黄146 作用下， 反应 18.0h， 生成 N-(2,3-dihydro-3-oxopyridazin-6-yl)methylamine hydrochloride
  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