7-(2-Chloro-5-methyl-imidazo[1,5-b]pyridazin-7-yl)-1-phenyl-heptan-1-one | 152533-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(2-Chloro-5-methyl-imidazo[1,5-b]pyridazin-7-yl)-1-phenyl-heptan-1-one
• 英文别名: 1-Heptanone, 7-(2-chloro-5-methylimidazo(1,5-b)pyridazin-7-yl)-1-phenyl-；7-(2-chloro-5-methylimidazo[1,5-b]pyridazin-7-yl)-1-phenylheptan-1-one
• CAS: 152533-92-1
• 化学式: C₂₀H₂₂ClN₃O
• 分子量: 355.867
• InChiKey: IBKVKGUXDNYYIR-UHFFFAOYSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(2-Chloro-5-methyl-imidazo[1,5-b]pyridazin-7-yl)-1-phenyl-heptan-1-one 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 84.0h， 生成 7-(2-Imidazol-1-yl-5-methyl-imidazo[1,5-b]pyridazin-7-yl)-1-phenyl-heptan-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：

  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

文献信息

• A visible-light mediated ring opening reaction of alkylidenecyclopropanes for the generation of homopropargyl radicals
  作者：Xiao-Yu Zhang、Chao Ning、Ben Mao、Yin Wei、Min Shi

  DOI：10.1039/d1sc01889b

  日期：——

  Classical cyclopropylcarbinyl radical clock reactions have been widely applied to conduct mechanistic studies for probing radical processes for a long time; however, alkylidenecyclopropanes, which have a similar molecular structure to methylcyclopropanes, surprisingly have not yet attracted researcher's attention for similar ring opening radical clock processes. In recent years, photocatalytic NHPI

  经典的环丙基羰基自由基时钟反应长期以来被广泛应用于探测自由基过程的机理研究；然而，与甲基环丙烷具有相似分子结构的亚烷基环丙烷令人惊讶地尚未因类似的开环自由基时钟过程而引起研究人员的注意。近年来，光催化NHPI酯活化化学取得了长足的发展，为交叉偶联反应提供了新的合成路线。在此，我们希望报道一种在光氧化还原催化下使用带有亚烷基环丙烷的创新NHPI酯的非经典开环自由基时钟反应，为直接制备各种炔基衍生物提供全新的合成方法。该方案的潜在合成效用在生物活性分子或其衍生物和药用物质的多种转化和简便合成中得到证明。
• 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.