N-(3-amino-2-hydroxypropyl)-2(R)-[1-(2,2-dimethylpropionyl)-pyrrolidine-2(S)-carbonylamino]-3-naphthalen-2-yl-propionamide | 289050-98-2

• 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: N-(3-amino-2-hydroxypropyl)-2(R)-[1-(2,2-dimethylpropionyl)-pyrrolidine-2(S)-carbonylamino]-3-naphthalen-2-yl-propionamide
• 英文别名: (2S)-N-[(2R)-1-[(3-amino-2-hydroxypropyl)amino]-3-naphthalen-2-yl-1-oxopropan-2-yl]-1-(2,2-dimethylpropanoyl)pyrrolidine-2-carboxamide
• CAS: 289050-98-2
• 化学式: C₂₆H₃₆N₄O₄
• 分子量: 468.596
• InChiKey: WZNCDKPQYCCVNQ-PDQYLBCOSA-N

物化性质

• 沸点：
  819.1±65.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-amino-2-hydroxypropyl)-2(R)-[1-(2,2-dimethylpropionyl)-pyrrolidine-2(S)-carbonylamino]-3-naphthalen-2-yl-propionamide 、 异丁醛 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 (2S)-1-(2,2-dimethylpropanoyl)-N-[(2R)-1-[[2-hydroxy-3-(2-methylpropylamino)propyl]amino]-3-naphthalen-2-yl-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Novel amide derivatives as growth hormone secretagogues

  摘要：

  本发明揭示了一种作为生长激素分泌素的新化合物，其结构式为I：其中R1是取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、或取代或未取代的氨基，X为—CO—或—SO2—，Y为：其中n为0-4的整数，R4为氢、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基，R5和R6独立地选自氢、取代或未取代的烷基，或R5和R6或R4和R5一起形成取代或未取代的烷基烯，R2为氢或取代或未取代的烷基，R3为取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基，D为取代或未取代的氨基、取代或未取代的烷氧基，或取代或未取代的烷硫基，*代表一个不对称中心，以及在人类或动物体内具有生长激素释放活性的药用可接受的盐和各个异构体。

  公开号：

  US20060014701A1
• 作为产物：
  描述：

  N-pivaloyl-L-proline 在 N-甲基吗啉 、 1-羟基苯并三唑 、 一水合肼 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3-amino-2-hydroxypropyl)-2(R)-[1-(2,2-dimethylpropionyl)-pyrrolidine-2(S)-carbonylamino]-3-naphthalen-2-yl-propionamide
  参考文献：
  名称：

  Novel Series of Highly Potent Non-peptide Growth Hormone Secretagogues with Im- proved Bioavailability

  摘要：

  The discovery and the SAR of acylproline derivatives as highly potent growth hormone secretagogues (GHSs) with good oral bioavailability are described. One representative compound, N-[3-(2,2-dimethylpropylamino)-2hydroxypropyl]-2(R)-[ 1-(2,2-dimethylpropionyl)pyrrolidine-2(S)-carbonylamino]3-naphthalen-2-ylpropionamide (4e), showed potent GHS activity (ED50=1 nM) and good oral bioavailability (BA=33.2%). Moreover, the optically pure N-[3-(2,2-dimethylpropylamino)-2(S)-hydroxypropyl]-2(R)-[ I -(2,2-dimethylpropionyl)pyrrolidine-2(S)-carbonylamino]-3-naphthalen-2-ylpropionamide ((2S)-4c) showed a good metabolic stability against in vitro clearance (human liver microsome) with potent GHS activity.

  DOI：

  10.3987/com-05-s(t)73

文献信息

• NERVE PROTECTIVE DRUGS
  申请人：KAKEN PHARMACEUTICAL CO., LTD.

  公开号：EP1258250B1

  公开（公告）日：2005-09-14
• METHODS OF TREATING NEURODEGENERATIVE CONDITIONS
  申请人：Oxeia Biopharmaceuticals, Inc.

  公开号：US20170121385A1

  公开（公告）日：2017-05-04

  The present disclosure provides methods for treating a neurodegenerative condition or situation in a subject in need thereof, comprising administering to the subject an effective amount of a compound comprising ghrelin or a ghrelin variant.
• METHODS OF TREATING TRAUMATIC BRAIN INJURY
  申请人：OXEIA BIOPHARMACEUTICALS, INC.

  公开号：US20170266257A1

  公开（公告）日：2017-09-21

  The present disclosure provides methods for treating traumatic brain injury and other neurological disorders in a subject in need thereof, comprising administering to the subject an effective amount of a composition comprising ghrelin or a ghrelin variant. This invention provides for methods for treating a severe or moderate traumatic brain injury in a patient wherein said method comprises administering to the subject suffering from said severe or moderate traumatic brain injury a therapeutic effective amount of ghrelin or a ghrelin variant or a composition comprising ghrelin or a ghrelin variant so as to treat said severe or moderate traumatic brain injury.
• METHODS OF TREATING MILD BRAIN INJURY
  申请人：OXEIA BIOPHARMACEUTICALS, INC.

  公开号：US20170281732A1

  公开（公告）日：2017-10-05

  The present disclosure provides methods for treating mild brain injury and other neurological disorders in a subject in need thereof, comprising administering to the subject an effective amount of a compound comprising a ghrelin or ghrelin variant. This invention provides for methods for treating a mild brain injury or concussion in a patient wherein said method comprises administering to the subject in need thereof suffering from said mild brain injury or concussion an effective amount of a ghrelin variant or a composition comprising a ghrelin variant so as to treat said mild brain injury or concussion.
• US6849597B2
  申请人：——

  公开号：US6849597B2

  公开（公告）日：2005-02-01