(S)-N-tert-butoxycarbonyl-4-(ethoxycarbonyl)phenylalaninol | 885022-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-tert-butoxycarbonyl-4-(ethoxycarbonyl)phenylalaninol
• 英文别名: 4-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-benzoic acid ethyl ester；ethyl 4-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]benzoate
• CAS: 885022-30-0
• 化学式: C₁₇H₂₅NO₅
• 分子量: 323.389
• InChiKey: FPBZPPUYZBNJGT-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N-tert-butoxycarbonyl-4-(ethoxycarbonyl)phenylalaninol 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.25h， 生成 (Z)-N-{(1S)-2-hydroxy-1-[[4-(ethoxycarbonyl)phenyl]methyl]ethyl}-9-octadecenamide
  参考文献：
  名称：

  Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake

  摘要：

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.

  DOI：

  10.1021/jm051226l
• 作为产物：
  描述：

  Boc-4-碘-L-苯丙氨酸 在 N-甲基吗啉 、 palladium diacetate 、 三乙胺 、 三苯基膦 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.75h， 生成 (S)-N-tert-butoxycarbonyl-4-(ethoxycarbonyl)phenylalaninol
  参考文献：
  名称：

  Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake

  摘要：

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.

  DOI：

  10.1021/jm051226l

文献信息

• OXAZOLINE DERIVATIVES
  申请人：Galley Guido

  公开号：US20110112080A1

  公开（公告）日：2011-05-12

  The invention relates to compounds of formula I wherein the definitions of X, R and R 1 are as defined herein. The compounds of formula I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds can be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  该发明涉及公式I中的化合物，其中X、R和R1的定义如本文所述。公式I中的化合物对痕量胺相关受体（TAARs）有良好的亲和力，特别是对TAAR1。这些化合物可用于治疗抑郁症、焦虑障碍、躁郁症、注意力缺陷多动障碍（ADHD）、与压力相关的障碍、精神分裂症等精神障碍、帕金森病等神经疾病、阿尔茨海默病等神经退行性疾病、癫痫、偏头痛、高血压、物质滥用和代谢性障碍，如进食障碍、糖尿病、糖尿病并发症、肥胖、血脂异常、能量消耗和吸收障碍、体温稳态障碍、睡眠和昼夜节律障碍以及心血管疾病。
• OXAZOLINE DERIVATIVES FOR TREATMENT OF CNS DISORDERS.
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2499121B1

  公开（公告）日：2015-10-07
• US8354441B2
  申请人：——

  公开号：US8354441B2

  公开（公告）日：2013-01-15
• [EN] OXAZOLINE DERIVATIVES FOR TREATMENT OF CNS DISORDERS<br/>[FR] DÉRIVÉS D'OXAZOLINE POUR LE TRAITEMENT DE TROUBLES DU SYSTÈME NERVEUX CENTRAL (CNS)
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011057973A1

  公开（公告）日：2011-05-19

  The invention relates to compounds of formula (I) wherein the definitions of X, R and R1 are provided in claim 1. It has now been found that the compounds of formula (I) have a good affinity to the trace amine associated receptors (TAARs), especially for TAARl. The compounds may be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.
• Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake
  作者：Aniello Schiano Moriello、Laurence Balas、Alessia Ligresti、Maria Grazia Cascio、Thierry Durand、Enrico Morera、Giorgio Ortar、Vincenzo Di Marzo

  DOI：10.1021/jm051226l

  日期：2006.4.1

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.