(S)- 1-氧代-1-(2-氧代-2-苯乙胺)丙烷-2-取代氨甲酸苄酯 | 864825-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)- 1-氧代-1-(2-氧代-2-苯乙胺)丙烷-2-取代氨甲酸苄酯
• 中文别名: (S)-1-氧代-1-(2-氧代-2-苯乙胺)丙烷-2-取代氨甲酸苄酯
• 英文名称: N2-[(benzyloxy)carbonyl]-N-(2-oxo-2-phenylethyl)-L-alaninamide
• 英文别名: Benzyl (S)-(1-oxo-1-((2-oxo-2-phenylethyl)amino)propan-2-YL)carbamate；benzyl N-[(2S)-1-oxo-1-(phenacylamino)propan-2-yl]carbamate
• CAS: 864825-19-4
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: YWJXSRRTCSHUAU-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)- 1-氧代-1-(2-氧代-2-苯乙胺)丙烷-2-取代氨甲酸苄酯 在 palladium 10% on activated carbon 、 ammonium acetate 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 (S)-1-(5-苯基-1H-咪唑-2-基)乙胺
  参考文献：
  名称：

  Identification of a dual δ OR antagonist/μ OR agonist as a potential therapeutic for diarrhea-predominant Irritable Bowel Syndrome (IBS-d)

  摘要：

  A small set of acyclic analogs 5 were prepared to explore their structure-activity relationships (SARs) relative to heterocyclic core, opioid receptor (OR) agonists 4. Compound 5l was found to have very favorable OR binding affinities at the δ and μ ORs (r K(i) δ=1.3 nM; r K(i) μ=0.9 nM; h K(i) μ=1.7 nM), with less affinity for the κ OR (gp K(i) κ=55 nM). The OR functional profile for 5l varied from the previously described dual δ/μ OR agonists 4, with 5l being a potent, mixed dual δ OR antagonist/μ OR agonist [δ IC(50)=89 nM (HVD); μ EC(50)=1 nM (GPI); κ EC(50)=1.6 μM (GPC)]. Compound 5l has progressed through a clinical Phase II Proof of Concept study on 800 patients suffering from diarrhea-predominant Irritable Bowel Syndrome (IBS-d). This Phase II study was recently completed successfully, with 5l demonstrating statistically significant efficacy over placebo.

  DOI：

  10.1016/j.bmcl.2012.05.042
• 作为产物：
  描述：

  苄氧羰基-L-丙氨酸 、 2-氨基苯乙酮盐酸盐 在 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 为溶剂， 以1.2 g的产率得到(S)- 1-氧代-1-(2-氧代-2-苯乙胺)丙烷-2-取代氨甲酸苄酯
  参考文献：
  名称：

  [EN] A PROCESS FOR THE PREPARATION OF ELUXADOLINE
  [FR] PROCÉDÉ DE PRÉPARATION DE L'ÉLUXADOLINE .

  摘要：

  本发明涉及一种改进的工艺，用于制备eluxadoline及其中间体，其中包括在制备N2-[(benzyloxy)carbonyl]-N-(2-oxo-2-phenylethyl)-L-alaninamide时使用水性表面活性剂溶液，该中间体是制备eluxadoline的中间体。

  公开号：

  WO2017208156A1

文献信息

• Novel compounds as opioid receptor modulators
  申请人：Breslin J. Henry

  公开号：US20050203143A1

  公开（公告）日：2005-09-15

  The present invention is directed to novel opioid receptor modulators of Formula (I). The invention further relates to methods for preparing such compounds, pharmaceutical compositions containing them, and their use in the treatment of disorders that may be ameliorated or treated by the modulation of opioid receptors.

  本发明涉及式(I)的新型阿片受体调节剂。该发明进一步涉及制备这类化合物的方法、包含它们的药物组合物，以及它们在治疗可通过调节阿片受体得到改善或治疗的疾病中的用途。
• Process for the preparation of opioid modulators
  申请人：Cai Chaozhong

  公开号：US20060211861A1

  公开（公告）日：2006-09-21

  The present invention is directed to novel processes for the preparation of opioid modulators (agonists and antagonists) and intermediates in their synthesis. The opioid modulators are useful for the treatment and prevention of as pain and gastrointestinal disorders.

  本发明涉及用于制备阿片类药物调节剂（激动剂和拮抗剂）及其合成中间体的新工艺。这些阿片类药物调节剂可用于治疗和预防疼痛和胃肠道疾病。
• [EN] PEPTIDOMIMETIC PROTEASOME INHIBITORS<br/>[FR] INHIBITEURS PEPTIDOMIMÉTIQUES DU PROTÉASOME
  申请人：UNIV CORNELL

  公开号：WO2019075252A1

  公开（公告）日：2019-04-18

  The compounds of the present invention are represented by the following compounds having Formula (I) and Formula (I'): where the substituents R, R1, R3 R4, R', W, X, Y, Z, k, and m are as defined herein and where the substituents R, R1, R2, R3, R4, X, Y, Z, and m are as defined herein. These compounds are used in the treatment of bacterial infections, parasite infections, fungal infections, cancer, immunologic disorders, autoimmune disorders, neurodegenerative diseases and disorders, inflammatory disorders, or muscular dystrophy or for providing immunosuppression for transplanted organs or tissues.

  本发明的化合物由具有式（I）和式（I'）的以下化合物表示：其中取代基R、R1、R3、R4、R'、W、X、Y、Z、k和m如本文所定义，取代基R、R1、R2、R3、R4、X、Y、Z和m如本文所定义。这些化合物用于治疗细菌感染、寄生虫感染、真菌感染、癌症、免疫紊乱、自身免疫性疾病、神经退行性疾病和紊乱、炎症性疾病，或肌肉萎缩症，或用于为移植的器官或组织提供免疫抑制。
• NOVEL COMPOUNDS AS OPIOID RECEPTOR MODULATORS
  申请人：Breslin Henry J.

  公开号：US20100324051A1

  公开（公告）日：2010-12-23

  The present invention is directed to novel opioid receptor modulators of Formula (I). The invention further relates to methods for preparing such compounds, pharmaceutical compositions containing them, and their use in the treatment of disorders that may be ameliorated or treated by the modulation of opioid receptors.

  本发明涉及一种新型的阿片受体调节剂，其化学式为(I)。本发明还涉及制备这些化合物的方法、包含它们的药物组合物以及它们在调节阿片受体治疗可能被改善或治疗的疾病方面的应用。
• PROCESS FOR THE PREPARATION OF OPIOD MODULATORS
  申请人：Cai Chaozhong

  公开号：US20100036132A1

  公开（公告）日：2010-02-11

  The present invention is directed to novel processes for the preparation of opioid modulators (agonists and antagonists) and intermediates in their synthesis. The opioid modulators are useful for the treatment and prevention of as pain and gastrointestinal disorders.

  本发明涉及制备阿片类调节剂（激动剂和拮抗剂）及其合成中间体的新型工艺。这些阿片类调节剂可用于治疗和预防疼痛和胃肠道疾病。