(S)-2-isobutyl-5-[N-(9-fluorenylmethoxycarbonyl)amino]pentanoic acid | 1085965-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2-isobutyl-5-[N-(9-fluorenylmethoxycarbonyl)amino]pentanoic acid
• 英文别名: (S)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-isobutylpentanoic acid；(2S)-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propyl]-4-methylpentanoic acid
• CAS: 1085965-68-9
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: CDEVLAKYBISKGZ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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 、 (S)-2-isobutyl-5-[N-(9-fluorenylmethoxycarbonyl)amino]pentanoic 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362 mg的产率得到(S)-2-isobutyl-5-[N-(9-fluorenylmethoxycarbonyl)amino]pentanoic 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
• Development of Novel Neurokinin 3 Receptor (NK3R) Selective Agonists with Resistance to Proteolytic Degradation
  作者：Ryosuke Misu、Shinya Oishi、Ai Yamada、Takashi Yamamura、Fuko Matsuda、Koki Yamamoto、Taro Noguchi、Hiroaki Ohno、Hiroaki Okamura、Satoshi Ohkura、Nobutaka Fujii

  DOI：10.1021/jm500771w

  日期：2014.10.23

  Neurokinin B (NKB) regulates the release of gonadotropin-releasing hormone (GnRH) via activation of the neurokinin-3 receptor (NK3R). We evaluated the biological stability of NK3R selective agonists to develop novel NK3R agonists to regulate reproductive functions. On the basis of degradation profiles, several peptidomimetic derivatives were designed. The modification of senktide with (E)-alkene dipeptide isostere generated a novel potent NK3R agonist with high stability and prolonged bioactivity.
• 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.