(4R,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-4-hydroxy-2-isobutyl-2-pentenoic acid | 1085965-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (4R,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-4-hydroxy-2-isobutyl-2-pentenoic acid
• 英文别名: (4R,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-4-hydroxy-2-isobutylpent-2-enoic acid；(E,4R)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-2-(2-methylpropyl)pent-2-enoic acid
• CAS: 1085965-74-7
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: FOWFJIPFPSAMIB-NWNNTGRJSA-N

物化性质

• 沸点：
  672.6±55.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三乙基氯硅烷 、 (4R,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-4-hydroxy-2-isobutyl-2-pentenoic acid 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以55%的产率得到(4R,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-isobutyl-4-triethylsiloxy-2-pentenoic acid
  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：

  C₉H₁₇NO₃ 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以1.02 g的产率得到(4R,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-4-hydroxy-2-isobutyl-2-pentenoic acid
  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

文献信息

• METASTIN DERIVATIVE AND USE THEREOF
  申请人：Kyoto University

  公开号：EP2275433B1

  公开（公告）日：2017-06-07
• US8592379B2
  申请人：——

  公开号：US8592379B2

  公开（公告）日：2013-11-26
• Development of Novel G-Protein-Coupled Receptor 54 Agonists with Resistance to Degradation by Matrix Metalloproteinase
  作者：Kenji Tomita、Shinya Oishi、Hiroaki Ohno、Stephen C. Peiper、Nobutaka Fujii

  DOI：10.1021/jm800930w

  日期：2008.12.11

  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.