(E)-2-isobutyl-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-pentenoic acid | 1085965-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (E)-2-isobutyl-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-pentenoic acid
• 英文别名: (E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-isobutylpent-2-enoic acid；(E)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(2-methylpropyl)pent-2-enoic acid
• CAS: 1085965-69-0
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: FNRDZOCXZVRVHW-CAOOACKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 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：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对氟苯甲酸 、 (E)-2-isobutyl-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-pentenoic acid 、 Fmoc-L-苯丙氨酸 、 Fmoc-L-色氨酸 、 三氟乙酸 、 Fmoc-Pbf-L-精氨酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 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：

  、 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， 以428 mg的产率得到(E)-2-isobutyl-5-[N-(9-fluorenylmethoxycarbonyl)amino]-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：Fujii Nobutaka

  公开号：US20110039786A1

  公开（公告）日：2011-02-17

  The present invention provides a metastin derivative represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof, or a pharmaceutical composition containing it. The metastin derivative or a salt thereof is superior in blood stability, and has a cancer metastasis suppressive action or cancer growth suppressive action.

  本发明提供了一种由式(I)表示的metastin衍生物，其中每个符号如规范中所定义，或其盐，或含有其的药物组合物。该metastin衍生物或其盐具有较好的血液稳定性，并具有抑制癌转移或抑制癌细胞生长的作用。
• 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.