Diethyl 2-[[(1,3-dibenzyl-2,6-dioxopyrimidin-4-yl)amino]methylidene]propanedioate | 1145655-75-9

• 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: Diethyl 2-[[(1,3-dibenzyl-2,6-dioxopyrimidin-4-yl)amino]methylidene]propanedioate
• CAS: 1145655-75-9
• 化学式: C₂₆H₂₇N₃O₆
• 分子量: 477.517
• InChiKey: RXVOISSBRQWGNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Diethyl 2-[[(1,3-dibenzyl-2,6-dioxopyrimidin-4-yl)amino]methylidene]propanedioate 以 二苯醚 、 联苯 为溶剂， 反应 1.0h， 以74.2%的产率得到
  参考文献：
  名称：

  A heterocyclic molecule with significant activity against dengue virus

  摘要：

  There are no specific approved drugs or vaccines for the treatment or prevention of infectious dengue virus and there are very few compounds known that inhibit the replication of this virus. This letter describes the concise synthesis of two uracil-based multifunctional compounds. One of these compounds (1) has strong activity against dengue virus. It also exhibits low activity against a few other RNA viruses, but is highly active against yellow fever virus, a related flavivirus. It is likely that the mechanism of action of the antiviral activity of this compound is through its inhibition of the enzyme, inosine monophosphate dehydrogenase (IMPDH). Molecular modeling studies reveal that the compound can have specific hydrogen bonding interactions with a number of amino acids in the active site of IMPDH, a stacking interaction with the bound natural substrate, IMP, and the ability to interfere with the binding of NAD(+) with IMPDH, prior to the hydration step. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.031
• 作为产物：
  描述：

  1,3-dibenzyl-6-aminouracil 、 乙氧基甲叉丙二酸二乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以41.8%的产率得到Diethyl 2-[[(1,3-dibenzyl-2,6-dioxopyrimidin-4-yl)amino]methylidene]propanedioate
  参考文献：
  名称：

  A heterocyclic molecule with significant activity against dengue virus

  摘要：

  There are no specific approved drugs or vaccines for the treatment or prevention of infectious dengue virus and there are very few compounds known that inhibit the replication of this virus. This letter describes the concise synthesis of two uracil-based multifunctional compounds. One of these compounds (1) has strong activity against dengue virus. It also exhibits low activity against a few other RNA viruses, but is highly active against yellow fever virus, a related flavivirus. It is likely that the mechanism of action of the antiviral activity of this compound is through its inhibition of the enzyme, inosine monophosphate dehydrogenase (IMPDH). Molecular modeling studies reveal that the compound can have specific hydrogen bonding interactions with a number of amino acids in the active site of IMPDH, a stacking interaction with the bound natural substrate, IMP, and the ability to interfere with the binding of NAD(+) with IMPDH, prior to the hydration step. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.031