(3(2S,3R),4R)-3-<2-Azido-3-(4-methoxyphenyl)butyroyl>-4-phenyl-2-oxazolidinone | 151908-49-5

• 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: (3(2S,3R),4R)-3-<2-Azido-3-(4-methoxyphenyl)butyroyl>-4-phenyl-2-oxazolidinone
• 英文别名: (R)-3-((2S,3R)-2-azido-3-(4-methoxyphenyl)-butanoyl)-4-phenyl-oxazolidin-2-one；(4R)-3-[(2S,3R)-2-azido-3-(4-methoxyphenyl)butanoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 151908-49-5
• 化学式: C₂₀H₂₀N₄O₄
• 分子量: 380.403
• InChiKey: NZFYZLLMZQSARH-BVGQSLNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3(2S,3R),4R)-3-<2-Azido-3-(4-methoxyphenyl)butyroyl>-4-phenyl-2-oxazolidinone 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢溴酸 、 氢气 、 双氧水 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 21.75h， 生成 threo-L-(2S,3R)-β-Methyltyrosine
  参考文献：
  名称：

  Efficient method for the total asymmetric synthesis of the isomers of .beta.-methyltyrosine

  摘要：

  Alpha-Amino acids modified at the beta-carbon atom can provide topographical constraints when incorporated into a peptide. Such modifications can modulate the physical, chemical, and biological properties of the compound. In order to properly evaluate the effect of such modifications, large-scale asymmetric syntheses of the isomers are needed. A method for the stereoselective large-scale synthesis of an four stereoisomers of beta-methyltyrosine is described in this paper. The stereochemistry of both the alpha- and beta-stereocenters was set using 4-phenyl-2-oxazolidinone as a chiral auxiliary. The key reactions were an asymmetric Michael-like addition of an organocuprate to a chiral alpha,beta-unsaturated acyloxazolidinone (beta center) and subsequent stereoselective electrophilic bromination of the resulting product (alpha center). Conversion of the bromide to the azide, catalyzed hydrolysis to the azido acid with simultaneous recovery of the chiral auxiliary, reduction of the azide, and final deprotection of the phenol group afforded the desired amino acids. In general, the reactions were performed in yields over 80 %, and the isomers were obtained in enantiomeric purities of 98:2 to 99:1.

  DOI：

  10.1021/jo00078a042
• 作为产物：
  描述：

  (R)-4-苯基-2-唑烷酮 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三氟甲磺酸二丁硼 、 叠氮化四丁基铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 13.5h， 生成 (3(2S,3R),4R)-3-<2-Azido-3-(4-methoxyphenyl)butyroyl>-4-phenyl-2-oxazolidinone
  参考文献：
  名称：

  Efficient method for the total asymmetric synthesis of the isomers of .beta.-methyltyrosine

  摘要：

  Alpha-Amino acids modified at the beta-carbon atom can provide topographical constraints when incorporated into a peptide. Such modifications can modulate the physical, chemical, and biological properties of the compound. In order to properly evaluate the effect of such modifications, large-scale asymmetric syntheses of the isomers are needed. A method for the stereoselective large-scale synthesis of an four stereoisomers of beta-methyltyrosine is described in this paper. The stereochemistry of both the alpha- and beta-stereocenters was set using 4-phenyl-2-oxazolidinone as a chiral auxiliary. The key reactions were an asymmetric Michael-like addition of an organocuprate to a chiral alpha,beta-unsaturated acyloxazolidinone (beta center) and subsequent stereoselective electrophilic bromination of the resulting product (alpha center). Conversion of the bromide to the azide, catalyzed hydrolysis to the azido acid with simultaneous recovery of the chiral auxiliary, reduction of the azide, and final deprotection of the phenol group afforded the desired amino acids. In general, the reactions were performed in yields over 80 %, and the isomers were obtained in enantiomeric purities of 98:2 to 99:1.

  DOI：

  10.1021/jo00078a042

文献信息

• Urea derivative or pharmacologically acceptable salt thereof
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：US10858314B2

  公开（公告）日：2020-12-08

  The present invention provides a urea compound or a pharmacologically acceptable salt thereof that has a formyl peptide receptor like 1 (hereinafter may be abbreviated as FPRL1) agonist effect, a pharmaceutical composition containing the urea compound or the pharmacologically acceptable salt thereof and a pharmaceutical use thereof. It has been found that a urea derivative represented by the general formula (I) below or a pharmacologically acceptable salt thereof has a superior FPRL1 agonist effect. Compound (I) or a pharmacologically acceptable salt thereof is highly useful for treatment, prevention, or suppression of inflammatory diseases, chronic airway diseases, cancers, septicemia, allergic symptoms, HIV retrovirus infection, circulatory disorders, neuroinflammation, nervous disorders, pains, prion diseases, amyloidosis, immune disorders and the like.

  本发明提供了一种具有类似甲酰肽受体1（以下可简称为FPRL1）激动剂效应的脲化合物或其药理学上可接受的盐、一种含有该脲化合物或其药理学上可接受的盐的药物组合物及其药物用途。研究发现，由以下通式（I）代表的脲衍生物或其药理学上可接受的盐具有优异的 FPRL1 激动剂效果。化合物(I)或其药理学上可接受的盐在治疗、预防或抑制炎症性疾病、慢性气道疾病、癌症、败血症、过敏症状、HIV逆转录病毒感染、循环系统疾病、神经炎症、神经紊乱、疼痛、朊病毒病、淀粉样变性、免疫紊乱等方面非常有用。
• UREA DERIVATIVE OR PHARMACOLOGICALLY ACCEPTABLE SALT THEREOF
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：EP3303284B1

  公开（公告）日：2020-04-08
• Efficient method for the total asymmetric synthesis of the isomers of .beta.-methyltyrosine
  作者：Ernesto Nicolas、K. C. Russell、J. Knollenberg、Victor J. Hruby

  DOI：10.1021/jo00078a042

  日期：1993.12

  Alpha-Amino acids modified at the beta-carbon atom can provide topographical constraints when incorporated into a peptide. Such modifications can modulate the physical, chemical, and biological properties of the compound. In order to properly evaluate the effect of such modifications, large-scale asymmetric syntheses of the isomers are needed. A method for the stereoselective large-scale synthesis of an four stereoisomers of beta-methyltyrosine is described in this paper. The stereochemistry of both the alpha- and beta-stereocenters was set using 4-phenyl-2-oxazolidinone as a chiral auxiliary. The key reactions were an asymmetric Michael-like addition of an organocuprate to a chiral alpha,beta-unsaturated acyloxazolidinone (beta center) and subsequent stereoselective electrophilic bromination of the resulting product (alpha center). Conversion of the bromide to the azide, catalyzed hydrolysis to the azido acid with simultaneous recovery of the chiral auxiliary, reduction of the azide, and final deprotection of the phenol group afforded the desired amino acids. In general, the reactions were performed in yields over 80 %, and the isomers were obtained in enantiomeric purities of 98:2 to 99:1.