(S)-α-phthalimido-N-(pyridin-2-yl)benzenepropanamide | 149116-21-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-α-phthalimido-N-(pyridin-2-yl)benzenepropanamide
• 英文别名: (2S)-2-(1,3-dioxoisoindol-2-yl)-3-phenyl-N-pyridin-2-ylpropanamide
• CAS: 149116-21-2
• 化学式: C₂₂H₁₇N₃O₃
• 分子量: 371.395
• InChiKey: LTBMNBSMHSEKQB-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-α-phthalimido-N-(pyridin-2-yl)benzenepropanamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (S)-2-amino-3-phenyl-N-(pyridin-2-yl)propanamide
  参考文献：
  名称：

  Synthesis and analgesic activities of urea derivatives of α-amino-N-pyridyl benzene propanamide

  摘要：

  New urea L-phenyl alanine derivatives of 4-aminopyridine have been synthesized and evaluated for analgesic activity with the PBQ writhing test in mice and the Randall-Selitto test in rats. Potent oral activity (ID50 < 10 mg/kg) and good tolerance were found in alkyl, arylalkyl and carboxyalkyl urea derivatives. The analgesic activity was found to be totally dependent on the pyridine moiety and was at least partly inhibited by pretreatment with (alpha) methyltyrosine, as was the case for 4-aminopyridine. These compounds are therefore pharmacologically interesting as new analgesic derivatives of 4-aminopyridine. They have a higher oral activity and a better activity/tolerance profile.

  DOI：

  10.1016/0223-5234(94)90070-1
• 作为产物：
  描述：

  2-氨基吡啶 、 phthaloyl-L-phenylalanyl chloride 以 四氢呋喃 、 三乙胺 为溶剂， 生成 (S)-α-phthalimido-N-(pyridin-2-yl)benzenepropanamide
  参考文献：
  名称：

  Analgesic .alpha.-amino-N-pyridylbenzenepropanamide derivatives and

  摘要：

  本发明涉及公式##STR1##的(S)构型衍生物，它们的加成盐以及它们在治疗中的应用，特别是作为具有镇痛性质的药物。

  公开号：

  US05200408A1

文献信息

• Copper-Catalyzed Direct C(sp³)–H Alkoxylation to Access Quaternary α-Alkoxylated Amino Acid Derivatives
  作者：Qiang Wei、Yao Ma、Yi Dong、Gang Liu

  DOI：10.1021/acs.orglett.0c01853

  日期：2020.8.7

  prepare quaternary α-alkoxylated amino acid derivatives in good yields. This protocol can be applied to a series of α-amino acids bearing a variety of functional group substituents. Facile removal of the auxiliary directing group and tolerance of condensation conditions for amide bond formation enable the potential application of this method in the discovery of new peptide drugs in the future.

  开发了铜催化的C（sp 3）–H烷氧基化反应，以高产率制备季α-烷氧基化氨基酸衍生物。该方案可以应用于带有各种官能团取代基的一系列α-氨基酸。容易除去辅助指导基团和酰胺键形成的缩合条件的耐受性使该方法在将来发现新肽药物中的潜在应用成为可能。
• Analgesic .alpha.-amino-N-pyridylbenzenepropanamide derivatives and
  申请人：Laboratoires UPSA

  公开号：US05200408A1

  公开（公告）日：1993-04-06

  The present invention relates to the derivatives of the formula ##STR1## in the (S) configuration, to their addition salts and to their use in therapy, especially as drugs with analgesic properties.

  本发明涉及公式##STR1##的(S)构型衍生物，它们的加成盐以及它们在治疗中的应用，特别是作为具有镇痛性质的药物。
• US5200408A
  申请人：——

  公开号：US5200408A

  公开（公告）日：1993-04-06
• Synthesis and analgesic activities of urea derivatives of α-amino-N-pyridyl benzene propanamide
  作者：E Sartori、F Camy、JM Teulon、F Camborde、J Meignen、F Hertz、A Cloarec

  DOI：10.1016/0223-5234(94)90070-1

  日期：1994.1

  New urea L-phenyl alanine derivatives of 4-aminopyridine have been synthesized and evaluated for analgesic activity with the PBQ writhing test in mice and the Randall-Selitto test in rats. Potent oral activity (ID50 < 10 mg/kg) and good tolerance were found in alkyl, arylalkyl and carboxyalkyl urea derivatives. The analgesic activity was found to be totally dependent on the pyridine moiety and was at least partly inhibited by pretreatment with (alpha) methyltyrosine, as was the case for 4-aminopyridine. These compounds are therefore pharmacologically interesting as new analgesic derivatives of 4-aminopyridine. They have a higher oral activity and a better activity/tolerance profile.