(4S,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-isobutyl-4-(triethylsiloxy)pent-2-enoic acid | 1085965-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (4S,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-isobutyl-4-(triethylsiloxy)pent-2-enoic acid
• 英文别名: (4S,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-isobutyl-4-triethylsiloxy-2-pentenoic acid；(E,4S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(2-methylpropyl)-4-triethylsilyloxypent-2-enoic acid
• CAS: 1085965-78-1
• 化学式: C₃₀H₄₁NO₅Si
• 分子量: 523.745
• InChiKey: AKJASDUUYSSLKW-OILDRBDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对氟苯甲酸 、 (4S,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-isobutyl-4-(triethylsiloxy)pent-2-enoic 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 N-[(2S)-1-[[(E,2S)-4-[[(2S)-1-[[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]carbamoyl]-2-hydroxy-6-methylhept-3-enyl]amino]-1-oxo-3-phenylpropan-2-yl]-4-fluorobenzamide;2,2,2-trifluoroacetic 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：

  三乙基氯硅烷 、 (4S,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95%的产率得到(4S,2E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-isobutyl-4-(triethylsiloxy)pent-2-enoic 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

• 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.