N-(tert-butoxycarbonyl)-3-(9,10-dihydro-9-anthryl)-DL-alanine | 82317-90-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: N-(tert-butoxycarbonyl)-3-(9,10-dihydro-9-anthryl)-DL-alanine
• CAS: 82317-90-6
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: FFYJVXWMGKAYCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 、 3-(9,10-dihydro-9-anthryl)-DL-alanine 在 sodium hydroxide 、 magnesium oxide 作用下， 以 1,4-二氧六环 为溶剂， 以86%的产率得到N-(tert-butoxycarbonyl)-3-(9,10-dihydro-9-anthryl)-DL-alanine
  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