(3R,5SR)-5-(azidomethyl)-3-isobutyldihydrofuran-2(3H)-one | 1085965-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,5SR)-5-(azidomethyl)-3-isobutyldihydrofuran-2(3H)-one
• CAS: 1085965-93-0
• 化学式: C₉H₁₅N₃O₂
• 分子量: 197.237
• InChiKey: VMZUCYARFBRLJV-GVHYBUMESA-N

反应信息

• 作为反应物：
  描述：

  (3R,5SR)-5-(azidomethyl)-3-isobutyldihydrofuran-2(3H)-one 在 水 、 lithium hydroxide 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  Development of Novel G-Protein-Coupled Receptor 54 Agonists with Resistance to Degradation by Matrix Metalloproteinase

  摘要：

  Kisspeptin-GPR54 signaling is involved in the suppression of cancer metastasis and regulation of hormonal secretion. Recently, matrix metalloproteinase mediated deactivation of kisspeptins through hydrolysis of the Gly-Leu peptide bond has been reported. In the present report, GPR54 agonistic peptides having several nonhydrolyzable Gly-Leu dipeptide isosteres were designed and synthesized. (E)-Alkene- and hydroxyethylene-type isostere-containing analogues maintained the original activity with higher stability in murine serum and resistance to MMP-9-mediated cleavage.

  DOI：

  10.1021/jm800930w
• 作为产物：
  描述：

  在 sodium azide 、 氯化铵 作用下， 以 甲醇 为溶剂， 以1.86 g的产率得到(3R,5SR)-5-(azidomethyl)-3-isobutyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Development of Novel G-Protein-Coupled Receptor 54 Agonists with Resistance to Degradation by Matrix Metalloproteinase

  摘要：

  Kisspeptin-GPR54 signaling is involved in the suppression of cancer metastasis and regulation of hormonal secretion. Recently, matrix metalloproteinase mediated deactivation of kisspeptins through hydrolysis of the Gly-Leu peptide bond has been reported. In the present report, GPR54 agonistic peptides having several nonhydrolyzable Gly-Leu dipeptide isosteres were designed and synthesized. (E)-Alkene- and hydroxyethylene-type isostere-containing analogues maintained the original activity with higher stability in murine serum and resistance to MMP-9-mediated cleavage.

  DOI：

  10.1021/jm800930w