2-hydroxy-1,3-dioxo-N-(prop-2-yn-1-yl)isoindoline-5-carboxamide | 782450-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-hydroxy-1,3-dioxo-N-(prop-2-yn-1-yl)isoindoline-5-carboxamide
• 英文别名: 2-hydroxy-1,3-dioxo-N-prop-2-ynylisoindole-5-carboxamide
• CAS: 782450-41-3
• 化学式: C₁₂H₈N₂O₄
• 分子量: 244.207
• InChiKey: SYFZFLXRHOAKIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86.71
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-1,3-dioxo-N-(prop-2-yn-1-yl)isoindoline-5-carboxamide 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 1,3-Dioxo-2-trityloxy-2,3-dihydro-1H-isoindole-5-carboxylic acid (1-benzyl-1H-[1,2,3]triazol-4-ylmethyl)-amide
  参考文献：
  名称：

  用聚合物负载的N-羟基邻苯二甲酰亚胺合成复杂的烷氧基胺

  摘要：

  描述了聚合物负载的N-羟基邻苯二甲酰亚胺的合成。聚苯乙烯结合的N-羟基邻苯二甲酰亚胺树脂1已经用于制备同时显示立体化学和位置多样性的复杂烷氧基胺。还概述了有效地使复杂的烷氧基胺与醛和酮缩合的方法。

  DOI：

  10.1016/j.tet.2004.05.109
• 作为产物：
  描述：

  偏苯三酸酐 在 吡啶 、 氯化亚砜 、 羟胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-hydroxy-1,3-dioxo-N-(prop-2-yn-1-yl)isoindoline-5-carboxamide
  参考文献：
  名称：

  Modular RNA regulators and methods

  摘要：

  本公开描述了模块化miRNA调控分子及使用模块化miRNA调控分子的方法。一般来说，模块化miRNA调控分子包括一个识别模块和一个抑制模块。一般来说，识别模块包括一个多核苷酸，其中至少有一部分多核苷酸识别预选的预miRNA的至少一部分。一般来说，抑制模块包括一个能抑制核酸酶加工预选的预RNA至成熟RNA的基团。

  公开号：

  US10093929B2

文献信息

• Bifunctional small molecule-oligonucleotide hybrid as microRNA inhibitor
  作者：Umesh Bhattarai、Wei-Che Hsieh、Hao Yan、Zhi-Fo Guo、Ashif Yasin Shaikh、Aria Soltani、Yabin Song、Danith H. Ly、Fu-Sen Liang

  DOI：10.1016/j.bmc.2020.115394

  日期：2020.4

  miRNAs are key regulators of various biological processes. Dysregulation of miRNA is linked to many diseases. Development of miRNA inhibitor has implication in disease therapy and study of miRNA function. The biogenesis pathway of miRNA involves the processing of pre-miRNA into mature miRNA by Dicer enzyme. We previously reported a proximity enabled approach that employs bifunctional small molecules to regulate miRNA maturation through inhibiting the enzymatic activity of Dicer. By conjugating to an RNA targeting unit, an RNase inhibitor could be delivered to the cleavage site of specific pre-miRNA to deactivate the complexed Dicer enzyme. Herein, we expanded this bifunctional strategy by showing that antisense oligonucleotides (ASOs), including morpholinos and gamma PNAs, could be readily used as the RNA recognition unit to generate bifunctional small molecule-oligonucleotide hybrids as miRNA inhibitors. A systematic comparison revealed that the potency of these hybrids is mainly determined by the RNA binding of the targeting ASO molecules. Since the lengths of the ASO molecules used in this approach were much shorter than commonly used anti-miRNA ASOs, this may provide benefits to the specificity and cellular delivery of these hybrids. We expect that this approach could be complementary to traditional ASO and small molecule based miRNA inhibition and contribute to the study of miRNA.