N1,N1-diethyl-N2-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-6-methoxypyrimidin-2-yl)propan-2-yl)oxalamide | 1370588-65-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N1,N1-diethyl-N2-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-6-methoxypyrimidin-2-yl)propan-2-yl)oxalamide
• 英文别名: N',N'-diethyl-N-[1-[4-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-6-methoxy-pyrimidin-2-yl]-1-methyl-ethyl]oxamide；N',N'-diethyl-N-[2-[4-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-6-methoxypyrimidin-2-yl]propan-2-yl]oxamide
• CAS: 1370588-65-0
• 化学式: C₂₂H₂₈FN₅O₅
• 分子量: 461.493
• InChiKey: RFGIDEJECPJDLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4,6-三甲基苯磺酰氯 、 N1,N1-diethyl-N2-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-6-methoxypyrimidin-2-yl)propan-2-yl)oxalamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以50%的产率得到2-(2-(2-(diethylamino)-2-oxoacetamido)propan-2-yl)-4-(4-fluorobenzylcarbamoyl)-6-methoxypyrimidin-5-yl 2,4,6-trimethylbenzenesulfonate
  参考文献：
  名称：

  Hydroxyl may not be indispensable for raltegravir: Design, synthesis and SAR Studies of raltegravir derivatives as HIV-1 inhibitors

  摘要：

  A series of raltegravir derivatives 20-42 were prepared and systematically evaluated for their anti-HIV activity. The bioassay results showed that most of the compounds possess good to excellent anti-HIV activity. Especially, compounds 25 and 35 with subpicomole IC50 values seemed to be the most potent anti-HIV agents among all of the reported synthesized compounds. These compounds may therefore be considered as new potent anti-HIV agents. The 5-hydroxyl modification of raltegravir derivatives significantly increased the anti-HIV activity, which indicates that the hydroxyl may not be indispensable for raltegravir. The introducing of acyl at 5-position of raltegravir derivatives is favorable for antiviral activity. In addition, a high-throughput cell-based assay method with pseudotyped virus stocks was developed and used to identify HIV inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.015
• 作为产物：
  描述：

  diethylamidooxalyl chloride 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.25h， 生成 N1,N1-diethyl-N2-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-6-methoxypyrimidin-2-yl)propan-2-yl)oxalamide
  参考文献：
  名称：

  Hydroxyl may not be indispensable for raltegravir: Design, synthesis and SAR Studies of raltegravir derivatives as HIV-1 inhibitors

  摘要：

  A series of raltegravir derivatives 20-42 were prepared and systematically evaluated for their anti-HIV activity. The bioassay results showed that most of the compounds possess good to excellent anti-HIV activity. Especially, compounds 25 and 35 with subpicomole IC50 values seemed to be the most potent anti-HIV agents among all of the reported synthesized compounds. These compounds may therefore be considered as new potent anti-HIV agents. The 5-hydroxyl modification of raltegravir derivatives significantly increased the anti-HIV activity, which indicates that the hydroxyl may not be indispensable for raltegravir. The introducing of acyl at 5-position of raltegravir derivatives is favorable for antiviral activity. In addition, a high-throughput cell-based assay method with pseudotyped virus stocks was developed and used to identify HIV inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.015

文献信息

• Hydroxyl may not be indispensable for raltegravir: Design, synthesis and SAR Studies of raltegravir derivatives as HIV-1 inhibitors
  作者：Ziwen Wang、Mingxiao Wang、Xue Yao、Yue Li、Wentao Qiao、Yunqi Geng、Yuxiu Liu、Qingmin Wang

  DOI：10.1016/j.ejmech.2012.02.015

  日期：2012.4

  A series of raltegravir derivatives 20-42 were prepared and systematically evaluated for their anti-HIV activity. The bioassay results showed that most of the compounds possess good to excellent anti-HIV activity. Especially, compounds 25 and 35 with subpicomole IC50 values seemed to be the most potent anti-HIV agents among all of the reported synthesized compounds. These compounds may therefore be considered as new potent anti-HIV agents. The 5-hydroxyl modification of raltegravir derivatives significantly increased the anti-HIV activity, which indicates that the hydroxyl may not be indispensable for raltegravir. The introducing of acyl at 5-position of raltegravir derivatives is favorable for antiviral activity. In addition, a high-throughput cell-based assay method with pseudotyped virus stocks was developed and used to identify HIV inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.