tert-butyl (4S,2E)-4-hydroxy-2-isobutyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]-2-pentenoate | 1085965-73-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (4S,2E)-4-hydroxy-2-isobutyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]-2-pentenoate
• 英文别名: tert-butyl (4S,2E)-4-hydroxy-2-isobutyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-enoate；tert-butyl (E,4S)-4-hydroxy-2-(2-methylpropyl)-5-[(2,4,6-trimethylphenyl)sulfonylamino]pent-2-enoate
• CAS: 1085965-73-6
• 化学式: C₂₂H₃₅NO₅S
• 分子量: 425.59
• InChiKey: ZQJAXOSSSBIPTP-GQEMFKIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S,2E)-4-hydroxy-2-isobutyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]-2-pentenoate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以94%的产率得到tert-butyl (4R,2E)-2-isobutyl-4,5-[N-(2,4,6-trimethylphenylsulfonyl)epimino]-pent-2-enoate
  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：

  methyl (2R)-1-((2,4,6-trimethylphenyl)sulfonyl)-2-aziridinecarboxylate 在 甲醇 、 copper(l) cyanide 、 二异丁基氢化铝 、 potassium carbonate 、 间氯过氧苯甲酸 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 39.17h， 生成 tert-butyl (4S,2E)-4-hydroxy-2-isobutyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]-2-pentenoate
  参考文献：
  名称：

  METASTIN DERIVATIVE AND USE THEREOF

  摘要：

  公开号：

  EP2275433B1

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 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.