ethyl 5-benzamido-4-oxovalerate | 68220-12-2

• 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: ethyl 5-benzamido-4-oxovalerate
• 英文别名: 5-Benzamido-4-oxopentansaeureethylester；5-benzoylamino-4-oxo-valeric acid ethyl ester；5-Benzoylamino-4-oxo-valeriansaeure-aethylester；δ-Benzamino-laevulinsaeure-aethylester；δ-Benzamino-γ-oxo-n-valeriansaeure-aethylester；Ethyl 5-benzamido-4-oxopentanoate
• CAS: 68220-12-2
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: VWBGSGFSIMEJNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-benzamido-4-oxovalerate 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 6-(benzoylamino-methyl)-4,5-dihydro-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
• 作为产物：
  描述：

  反式尿刊酸 在 palladium on activated charcoal 盐酸 、 氯化亚砜 、 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 100.0h， 生成 ethyl 5-benzamido-4-oxovalerate
  参考文献：
  名称：

  Altman, Janina; Shoef, Nurit; Wilchek, Meir, Journal of the Chemical Society. Perkin transactions I, 1984, # 1, p. 59 - 62

  摘要：

  DOI：

文献信息

• Windaus; Doerries; Jensen, Chemische Berichte, 1921, vol. 54, p. 2748
  作者：Windaus、Doerries、Jensen

  DOI：——

  日期：——
• ALTMAN, J.;SHOEF, N.;WILCHEK, M.;WARSHAWSKY, A., J. CHEM. SOC. PERKIN TRANS., 1984, N 1, 59-62
  作者：ALTMAN, J.、SHOEF, N.、WILCHEK, M.、WARSHAWSKY, A.

  DOI：——

  日期：——
• 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.
• Altman, Janina; Shoef, Nurit; Wilchek, Meir, Journal of the Chemical Society. Perkin transactions I, 1984, # 1, p. 59 - 62
  作者：Altman, Janina、Shoef, Nurit、Wilchek, Meir、Warshawsky, Abraham

  DOI：——

  日期：——