N-((1H-imidazol-2-yl)methyl)pterin-7-carboxamide | 1379508-04-9

• 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-((1H-imidazol-2-yl)methyl)pterin-7-carboxamide
• 英文别名: 2-amino-N-(1H-imidazol-2-ylmethyl)-4-oxo-3H-pteridine-7-carboxamide
• CAS: 1379508-04-9
• 化学式: C₁₁H₁₀N₈O₂
• 分子量: 286.253
• InChiKey: PZXRUPDYVHAVKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-methoxycarbonylpterin 、 1-(1H-咪唑-2-基)甲胺 以 甲醇 为溶剂， 以57%的产率得到N-((1H-imidazol-2-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

文献信息

• Optimized 5-Membered Heterocycle-Linked Pterins for the Inhibition of Ricin Toxin A
  作者：Jeff M. Pruet、Ryota Saito、Lawrence A. Manzano、Karl R. Jasheway、Paul A. Wiget、Ishan Kamat、Eric V. Anslyn、Jon D. Robertus

  DOI：10.1021/ml300099t

  日期：2012.7.12

  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.