3-(1-Bromo-naphthalen-2-yl)-2-tert-butoxycarbonylamino-propionic acid | 82317-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1-Bromo-naphthalen-2-yl)-2-tert-butoxycarbonylamino-propionic acid
• 英文别名: 3-(1-Bromonaphthalen-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid；3-(1-bromonaphthalen-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 82317-88-2
• 化学式: C₁₈H₂₀BrNO₄
• 分子量: 394.265
• InChiKey: AJOPHRNIBGLLPT-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  2-Acetylamino-3-(1-bromo-naphthalen-2-yl)-propionic acid 在 盐酸 、 sodium hydroxide 、 magnesium oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 3-(1-Bromo-naphthalen-2-yl)-2-tert-butoxycarbonylamino-propionic acid
  参考文献：
  名称：

  Synthesis and biological activity of some very hydrophobic superagonist analogs of luteinizing hormone-releasing hormone

  摘要：

  The effect of increased hydrophobicity at position 6 of luteinizing hormone-releasing hormone (LH-RH) has been investigated by the incorporation of a series of 15 very hydrophobic, unnatural D-amino acids at this position. The unnatural amino acids studied can be considered analogues of phenylalanine with carbocyclic aromatic side chains consisting of substituted phenyl (e.g., 2,4,6-trimethylphenyl, p-biphenyl) or polycyclic aromatic (e.g., naphthalene, anthracene) units. When enzymatic resolution (subtilisin Carlsberg) of the most hydrophobic amino acids failed, the racemic amino acids were incorporated, and the diastereomeric LH-RH analogues were resolved by preparative high-performance liquid chromatography. The analogues were synthesized by the solid-phase technique. All of the synthetic compounds were very potent LH-RH superagonists, but [6-(3-(2-naphthyl)-D-alanine)]LH-RH, [6-(3-(2-naphthyl)-D-alanine), 7-(N alpha-methylleucine)]LH-RH and [6-(3-(2,4,6-trimethylphenyl)-D-alanine)]LH-RH appear to be among the most potent LH-RH agonist analogues yet reported when tested in a rat estrus cyclicity suppression assay designed to show the paradoxical antifertility effects of these compounds [ED50 approximately 7 x 10(-8) g; twice daily in saline]. These analogues are twice as potent as [D-Trp6,ProNHEt9]LH-RH in this assay system (i.e., approximately 200 times the potency of LH-RH).

  DOI：

  10.1021/jm00349a006