N-(propyn-3-yl)pterin-7-carboxamide | 1379508-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: N-(propyn-3-yl)pterin-7-carboxamide
• 英文别名: 2-amino-4-oxo-N-prop-2-ynyl-3H-pteridine-7-carboxamide
• CAS: 1379508-11-8
• 化学式: C₁₀H₈N₆O₂
• 分子量: 244.213
• InChiKey: QELNFYMCEIDFHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(叠氮基甲基)吡啶 、 N-(propyn-3-yl)pterin-7-carboxamide 在 copper(ll) sulfate pentahydrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 以88%的产率得到N-((1-(pyridin-3-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)pterin-7-carboxamide
  参考文献：
  名称：

  Optimized 5-Membered Heterocycle-Linked Pterins for the Inhibition of Ricin Toxin A

  摘要：

  The optimization of a series of pterin amides for use as Ricin Toxin A (RTA) inhibitors is reported. On the basis of crystallographic data of a previous furan-linked pterin, various expanded furans were synthesized, linked to the pterin, and tested for inhibition. Concurrently, heteroanalogues of furan were explored, leading to the discovery of more potent triazole-linked pterins. Additionally, we discuss a dramatic improvement in the synthesis of these pterin amides via a dual role by diazabicycloundecene (DBU). This synthetic enhancement facilitates rapid diversification of the previously challenging pterin heterocycle, potentially aiding future medicinal research involving this structure.

  DOI：

  10.1021/ml300099t
• 作为产物：
  描述：

  7-methoxycarbonylpterin 、 炔丙胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 以84%的产率得到N-(propyn-3-yl)pterin-7-carboxamide
  参考文献：
  名称：

  Optimized 5-Membered Heterocycle-Linked Pterins for the Inhibition of Ricin Toxin A

  摘要：

  The optimization of a series of pterin amides for use as Ricin Toxin A (RTA) inhibitors is reported. On the basis of crystallographic data of a previous furan-linked pterin, various expanded furans were synthesized, linked to the pterin, and tested for inhibition. Concurrently, heteroanalogues of furan were explored, leading to the discovery of more potent triazole-linked pterins. Additionally, we discuss a dramatic improvement in the synthesis of these pterin amides via a dual role by diazabicycloundecene (DBU). This synthetic enhancement facilitates rapid diversification of the previously challenging pterin heterocycle, potentially aiding future medicinal research involving this structure.

  DOI：

  10.1021/ml300099t