N-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)pent-4-ynamide | 872433-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)pent-4-ynamide
• CAS: 872433-76-6
• 化学式: C₂₅H₁₇NO₆
• 分子量: 427.413
• InChiKey: SNSDDNFZPQUZLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105.09
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (6S,9R,12S,15R)-15-[[(5-azidopentyl)thio]methyl]-2,2,6,12-tetramethyl-4,7,10,13-tetraoxo-9-[[[3-[[(2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl]oxy]-propyl]thio]methyl]-3-oxa-5,8,11,14-tetraazahexadecan-16-oic acid 、 N-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)pent-4-ynamide 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 sodium ascorbate 、 三(3-羟丙基三唑甲基)胺 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 以65%的产率得到(2R)-3-[5-[4-[3-[(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)amino]-3-oxopropyl]triazol-1-yl]pentylsulfanyl]-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-[3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypropylsulfanyl]propanoyl]amino]propanoyl]amino]propanoic acid
  参考文献：
  名称：

  Native Chemical Ligation,Thiol–Ene Click: A Methodology for the Synthesis of Functionalized Peptides

  摘要：

  The sequential combination of native chemical ligation and thiol-ene radical chemistry (NCL-TEC) on the resulting cysteine thiol has been investigated as a methodology for rapidly accessing functionalized peptides. Three sequential cycles of native chemical ligation and subsequent thiyl radical reactions (including a free-radical-mediated desulfurization reaction) were carried out on a peptide backbone demonstrating the iterative nature of this process. The versatility of the thiyl radical reaction at cysteine was demonstrated through the introduction of a number of different side chains including an amino acid derivative, a carbohydrate group, and an alkyl azide. Conditions were developed that allowed the sequential NCL-TEC process to proceed in high yield.

  DOI：

  10.1021/jo4001542
• 作为产物：
  描述：

  炔丙基脲 、 5-氨基荧光素 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到N-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)pent-4-ynamide
  参考文献：
  名称：

  Native Chemical Ligation,Thiol–Ene Click: A Methodology for the Synthesis of Functionalized Peptides

  摘要：

  The sequential combination of native chemical ligation and thiol-ene radical chemistry (NCL-TEC) on the resulting cysteine thiol has been investigated as a methodology for rapidly accessing functionalized peptides. Three sequential cycles of native chemical ligation and subsequent thiyl radical reactions (including a free-radical-mediated desulfurization reaction) were carried out on a peptide backbone demonstrating the iterative nature of this process. The versatility of the thiyl radical reaction at cysteine was demonstrated through the introduction of a number of different side chains including an amino acid derivative, a carbohydrate group, and an alkyl azide. Conditions were developed that allowed the sequential NCL-TEC process to proceed in high yield.

  DOI：

  10.1021/jo4001542

文献信息

• 一种具有FTO抑制活性的金属配合物及其制法和应用
  申请人：南京师范大学

  公开号：CN116143843A

  公开（公告）日：2023-05-23

  本发明公开了一种具有FTO抑制活性的金属配合物，还公开了上述具有FTO抑制活性的金属配合物的制备方法和应用。本发明金属配合物将采用炔基修饰的FTO抑制剂与含叠氮基团的金属配合物前体通过CuAAC反应得到，金属配合物具有良好的抗癌活性和FTO抑制活性，一方面能够克服单独FTO抑制剂存在的靶标选择性差的问题，另一方面能够克服单纯的金属配合物(前体)作为抗肿瘤药物或抗肿瘤药物组分时存在毒副作用大的问题。