(S)-tert-butyl (2-((1-phenylethyl)amino)ethyl)carbamate | 622373-29-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-tert-butyl (2-((1-phenylethyl)amino)ethyl)carbamate
• 英文别名: [2-(1-phenylethylamino)ethyl]carbamic acid tert-butyl ester；tert-butyl N-[2-[[(1S)-1-phenylethyl]amino]ethyl]carbamate
• CAS: 622373-29-9
• 化学式: C₁₅H₂₄N₂O₂
• 分子量: 264.368
• InChiKey: PLWCYNYUEFZMED-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl (2-((1-phenylethyl)amino)ethyl)carbamate 在 lithium aluminium tetrahydride 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 48.0h， 生成 (R)-tert-butyl 4-(1-phenylethyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis and Separation of the Enantiomers of the Neuropeptide S Receptor Antagonist (9R/S)-3-Oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic Acid 4-Fluoro-benzylamide (SHA 68)

  摘要：

  This study reports the synthesis, chromatographic separation, and pharmacological evaluation of the two enantiomers of the neuropeptide S receptor (NPSR) antagonist (9R/S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (SHA 68). The (9R)-3-oxo-1, 1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (compound 10) and (9S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo [3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (compound 10a) were synthesized and their purity assessed by chiral chromatography. The absolute configuration of the enantiomer 10 has been assigned from the crystal structure of the corresponding (S)-phenyl ethyl amine derivative 8. Calcium mobilization studies performed on cells expressing the recombinant NPSR demonstrated that compound 10 is the active enantiomer while the contribution of 10a to the NPSR antagonist properties of the racemic mixture is negligible.

  DOI：

  10.1021/jm200138r
• 作为产物：
  描述：

  (S)-tert-butyl (2-oxo-2-((1-phenylethyl)amino)ethyl)carbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到(S)-tert-butyl (2-((1-phenylethyl)amino)ethyl)carbamate
  参考文献：
  名称：

  Synthesis and Separation of the Enantiomers of the Neuropeptide S Receptor Antagonist (9R/S)-3-Oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic Acid 4-Fluoro-benzylamide (SHA 68)

  摘要：

  This study reports the synthesis, chromatographic separation, and pharmacological evaluation of the two enantiomers of the neuropeptide S receptor (NPSR) antagonist (9R/S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (SHA 68). The (9R)-3-oxo-1, 1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (compound 10) and (9S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo [3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (compound 10a) were synthesized and their purity assessed by chiral chromatography. The absolute configuration of the enantiomer 10 has been assigned from the crystal structure of the corresponding (S)-phenyl ethyl amine derivative 8. Calcium mobilization studies performed on cells expressing the recombinant NPSR demonstrated that compound 10 is the active enantiomer while the contribution of 10a to the NPSR antagonist properties of the racemic mixture is negligible.

  DOI：

  10.1021/jm200138r

文献信息

• Identification and SAR of Glycine Benzamides as Potent Agonists for the GPR139 Receptor
  作者：Curt A. Dvorak、Heather Coate、Diane Nepomuceno、Michelle Wennerholm、Chester Kuei、Brian Lord、David Woody、Pascal Bonaventure、Changlu Liu、Timothy Lovenberg、Nicholas I. Carruthers

  DOI：10.1021/acsmedchemlett.5b00247

  日期：2015.9.10

  A focused high throughput screening for GPR139 was completed for a select 100K compounds, and new agonist leads were identified. Subsequent analysis and structure-activity relationship studies identified (S)-3-chloro-N-(2-oxo-2-((1-phenylethyl)amino)ethyl)benzamide 7c as a potent and selective agonist of hGPR139 with an EC50 = 16 nM. The compound was found to cross the blood-brain barrier and have good drug-like properties amenable for oral dosing in rat.
• TRIAZOLE DERIVATIVES AS TACHYKININ RECEPTOR ANTAGONISTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1501809B1

  公开（公告）日：2008-01-16
• [EN] PROTEIN KINASE C (PKC) THETA INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE LA PROTÉINE KINASE C (PKC) THÊTA
  申请人：[en]EVOMMUNE, INC.

  公开号：WO2024025896A2

  公开（公告）日：2024-02-01

  Provided are protein kinase C (PKC) theta inhibitor compounds. Also provided are methods of use of such compounds, as well as pharmaceutical compositions thereof.