3-Anthracen-9-yl-2-tert-butoxycarbonylamino-propionic acid | 190319-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-Anthracen-9-yl-2-tert-butoxycarbonylamino-propionic acid
• 英文别名: Boc-beta-(9-anthryl)-Ala-OH；3-anthracen-9-yl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 190319-98-3
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: GYXDEFFXDFOZMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  589.9±43.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-acetyl-DL-9-anthranylalanine 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-Anthracen-9-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

文献信息

• Studies on cyclic dipeptides, I: Aryl modifications ofcyclo-[Phe-His]
  作者：C. R. Noe、A. Weigand、S. Pirker

  DOI：10.1007/bf00807581

  日期：1996.10

  Seven new cyclic dipeptides have been synthesized and tested for their applicability as tools to elucidate the mechanism of formation of mandelonitrile with (SS)-cyclo-[Phe-His] type catalysts. Conformational analyses based on H-1 NMR spectra are presented for all prepared cyclic dipeptides.
• RECEPTOR-SELECTIVE SOMATOSTATIN ANALOGS
  申请人：THE SALK INSTITUTE FOR BIOLOGICAL STUDIES

  公开号：EP0871666A1

  公开（公告）日：1998-10-21
• US5750499A
  申请人：——

  公开号：US5750499A

  公开（公告）日：1998-05-12
• [EN] RECEPTOR-SELECTIVE SOMATOSTATIN ANALOGS<br/>[FR] ANALOGUES DE LA STOMATINE A AFFINITE SELECTIVE POUR UN RECEPTEUR
  申请人：THE SALK INSTITUTE FOR BIOLOGICAL STUDIES

  公开号：WO1997014715A1

  公开（公告）日：1997-04-24

  (EN) Analogs of SRIF which are selective for SSTR1 in contrast to the other cloned SRIF receptors. These analogs are useful in determining the tissue and cellular expression of the receptor SSTR1 and its biological role in the endocrine, exocrine and nervous system, as well as in regulating tumor growth. SRIF analog peptides, such as des-AA1,2,5[D-Trp8, IAmp9]-SRIF inhibit the binding of [125I-Tyr11]SRIF to the cloned human receptor SSTR1 but do not bind to mouse SSTR2 and SSTR3, human SSTR4 or rat SSTR5. By incorporating an iodinated tyrosine in position-2 in these selective SRIF analogs, a labelled compound useful in drug-screening methods is provided.(FR) L'invention porte sur des analogues du SRIF présentant une affinité sélective pour le SSTR1 par contraste avec les autres récepteurs clonés du SRIF. Lesdits analogues s'avèrent utiles pour évaluer l'expression tissulaire et cellulaire du récepteur SSTR1 et son rôle biologique dans les systèmes endocrinien, exocrinien et nerveux, ainsi que dans la régulation de la croissance des tumeurs. Des peptides analogues du SRIF tels que le des-AA1,2,5 [D-Trp8, IAmp9]-SRIF inhibent la fixation du [125I-Tyr11]SRIF au récepteur SSTR1 cloné, mais ne se fixent pas aux SSTR2 et SSTR3 de la souris, ni au SSTR4 de l'homme, ni au SSTR5 du rat. En incorporant une tyrosine iodée en position-2 dans ces analogues sélectifs du SRIF, on obtient un composé marqué utilisable pour le dépistage des drogues.
• Synthesis and biological activity of some very hydrophobic superagonist analogs of luteinizing hormone-releasing hormone
  作者：John J. Nestor、Teresa L. Ho、Richard A. Simpson、Bonnie L. Horner、Gordon H. Jones、Georgia I. McRae、Brian H. Vickery

  DOI：10.1021/jm00349a006

  日期：1982.7

  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).