D-Tryptophanamide, N-(phenylmethyl)glycyl-N-(2-phenylethyl)- | 540483-32-7

• 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: D-Tryptophanamide, N-(phenylmethyl)glycyl-N-(2-phenylethyl)-
• 英文别名: (2R)-2-[[2-(benzylamino)acetyl]amino]-3-(1H-indol-3-yl)-N-(2-phenylethyl)propanamide
• CAS: 540483-32-7
• 化学式: C₂₈H₃₀N₄O₂
• 分子量: 454.572
• InChiKey: MVLSQEIQTWLALY-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  86
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯乙胺 、 N-alpha-芴甲氧羰基-N-in-叔丁氧羰基-D-色氨酸 、 2-((((9H-芴-9-基)甲氧基)羰基)(苄基)氨基)乙酸 以9.8 mg的产率得到D-Tryptophanamide, N-(phenylmethyl)glycyl-N-(2-phenylethyl)-
  参考文献：
  名称：

  Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3

  摘要：

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.

  DOI：

  10.1021/jm0210921

文献信息

• G Protein-Coupled Receptor and Modulators Thereof For The Treatment of Gaba-Related Neurological Disorders Including Sleep-Related Disorders
  申请人：Bagnol Didier

  公开号：US20110038850A1

  公开（公告）日：2011-02-17

  The present invention relates to methods of using BRS-3 to screen candidate compounds as compounds suitable for the treatment of sleep-related disorders. Inverse agonists and antagonists of the invention are useful as therapeutic agents for promoting sleep and for preventing or treating sleep disorders ameliorated by promoting sleep, such as insomnia and the like. Agonists and partial agonists of the invention are useful as therapeutic agents for promoting wakefulness and for preventing or treating excessive sleepiness, such as excessive sleepiness associated with narcolepsy and the like. The invention further relates to methods of using a BRS-3 to screen candidate compounds as pharmaceutical agents for a GABA-related neurological disorder such as a sleep disorder, an anxiety disorder, a convulsive disorder, migraine, a depressive disorder, a psychotic disorder, or a cognitive disorder. Compounds of the invention encompass compounds having sleep-promoting, wakefulness-promoting, anxiolytic, anticonvulsant, antidepressant, antipsychotic, and cognition-enhancing activities.
• Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3
  作者：Dirk Weber、Claudia Berger、Peter Eickelmann、Jochen Antel、Horst Kessler

  DOI：10.1021/jm0210921

  日期：2003.5.1

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.