Boc-D-Ser-D-Ala-OBzl | 92261-75-1

• 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: Boc-D-Ser-D-Ala-OBzl
• 英文别名: benzyl (2R)-2-[[(2R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoate
• CAS: 92261-75-1
• 化学式: C₁₈H₂₆N₂O₆
• 分子量: 366.414
• InChiKey: DWLJTTZAWDGBNE-TZMCWYRMSA-N

物化性质

• 沸点：
  562.2±50.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-D-Ser-D-Ala-OBzl 在 四氯化碳 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 生成 PhO-CH2CO-D-Ala(βCl)-D-Ala-OBzl
  参考文献：
  名称：

  Synthesis of Analogs of D-Ala--D-Ala as Potential Inhibitors of Bacterial Cell Wall Biosynthesis.

  摘要：

  The syntheses of the L,L- and D,D-stereoisomers of N- phenoxyacetyl -X-alanine in which X = Ser, Ala( beta Cl ) or Arg, are described. The antibacterial activity of these peptides and some of their synthetic intermediates has been examined. Four of the intermediates in which X = Ala( beta Cl ) and Arg(NO2), which possess C-terminal benzyl ester groups, were active against viridans streptococci and Streptococcus agalactiae. The D,D-enantiomers were more active than the corresponding L,L-isomers. None of the compounds were active against beta-lactamase producing bacteria or acted as beta-lactamase inhibitors.

  DOI：

  10.3891/acta.chem.scand.38b-0005
• 作为产物：
  描述：

  BOC-D-丝氨酸 、 D-丙氨酸苄酯对甲苯磺酸盐 在 N-乙基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到Boc-D-Ser-D-Ala-OBzl
  参考文献：
  名称：

  Synthesis of Analogs of D-Ala--D-Ala as Potential Inhibitors of Bacterial Cell Wall Biosynthesis.

  摘要：

  The syntheses of the L,L- and D,D-stereoisomers of N- phenoxyacetyl -X-alanine in which X = Ser, Ala( beta Cl ) or Arg, are described. The antibacterial activity of these peptides and some of their synthetic intermediates has been examined. Four of the intermediates in which X = Ala( beta Cl ) and Arg(NO2), which possess C-terminal benzyl ester groups, were active against viridans streptococci and Streptococcus agalactiae. The D,D-enantiomers were more active than the corresponding L,L-isomers. None of the compounds were active against beta-lactamase producing bacteria or acted as beta-lactamase inhibitors.

  DOI：

  10.3891/acta.chem.scand.38b-0005

文献信息

• OXO-SUBSTITUTED COMPOUND
  申请人：Sumitomo Dainippon Pharma Co., Ltd.

  公开号：EP3786168A1

  公开（公告）日：2021-03-03

  Provided is a novel compound that has an excellent β-lactamase inhibitory effect. More specifically, provided is a compound represented by formula (1a), (1b) or (11) having an excellent β-lactamase inhibitory effect or a pharmaceutically acceptable salt thereof. By using this compound either in combination with a β-lactam drug or alone, a useful preventive or therapeutic agent for bacterial infections is provided. Also provided are useful preventive or therapeutic agents for treating various diseases with the combined use of the aforesaid compound and β-lactam drugs.

  本发明提供了一种新型化合物，它具有极佳的β-内酰胺酶抑制效果。更具体地说，本发明提供了一种由式（1a）、（1b）或（11）表示的化合物或其药学上可接受的盐，该化合物具有优异的β-内酰胺酶抑制作用。通过将该化合物与β-内酰胺类药物结合使用或单独使用，可提供一种有效的细菌感染预防或治疗药物。此外，还提供了联合使用上述化合物和β-内酰胺类药物治疗各种疾病的有效预防或治疗剂。
• Oxo-substituted compound
  申请人：SUMITOMO DAINIPPON PHARMA CO., LTD.

  公开号：US11066425B1

  公开（公告）日：2021-07-20

  Provided is a novel compound that has an excellent β-lactamase inhibitory effect. More specifically, provided is a compound represented by formula (1a), (1b) or (11) having an excellent β-lactamase inhibitory effect or a pharmaceutically acceptable salt thereof. By using this compound either in combination with a β-lactam drug or alone, a useful preventive or therapeutic agent for bacterial infections is provided. Also provided are useful preventive or therapeutic agents for treating various diseases with the combined use of the aforesaid compound and β-lactam drugs.

  本发明提供了一种新型化合物，它具有极佳的β-内酰胺酶抑制效果。更具体地说，本发明提供了一种由式（1a）、（1b）或（11）表示的化合物或其药学上可接受的盐，该化合物具有优异的β-内酰胺酶抑制作用。通过将该化合物与β-内酰胺类药物结合使用或单独使用，可提供一种有效的细菌感染预防或治疗药物。此外，还提供了联合使用上述化合物和β-内酰胺类药物治疗各种疾病的有效预防或治疗剂。