benzyl 1-[2-oxo-2-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]ethyl]cyclopentane-1-carboxylate | 158738-51-3

• 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: benzyl 1-[2-oxo-2-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]ethyl]cyclopentane-1-carboxylate
• CAS: 158738-51-3
• 化学式: C₂₁H₂₇NO₅
• 分子量: 373.449
• InChiKey: SFZJCUXSRAZLFG-QGZVFWFLSA-N

物化性质

• 沸点：
  517.0±23.0 °C(predicted)
• 密度：
  1.196±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 1-[2-oxo-2-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]ethyl]cyclopentane-1-carboxylate 在 lithium hydroxide 、 2,4,6-三异丙基苯磺酰叠氮化物 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 碳酸氢钠 、 溶剂黄146 、 sodium sulfite 作用下， 反应 0.15h， 生成 (S)-α-azido-1-(benzyloxycarbonyl)cyclopentaneacetic acid
  参考文献：
  名称：

  Peptidomimetic inhibitors of herpes simplex virus ribonucleotide reductase: a new class of antiviral agents

  摘要：

  We have been investigating a new class of antiviral compounds effective against herpes simplex virus (HSV) in vitro and in vivo. Antiviral activity results from inhibition of HSV ribonucleotide reductase (RR). The inhibitors are designed as mimics of the RR small subunit C-terminus, a region essential for RR subunit association and consequently enzymatic activity. Inhibition results from specific binding of the inhibitor to the HSV RR large subunit thereby preventing subunit association. This report details the structure-activity studies that lead to the identification of BILD 1263, a potent inhibitor of HSV RR subunit association (IC50, 0.2 nM) that also inhibits the replication of HSV types 1 and 2 in cell culture (EC(50), 3 and 4 mu M) and reduces the severity of HSV-1-induced keratitis in a murine ocular model. The discovery of inhibitors with in vitro antiviral activity results from a combination of improving inhibitor potency in a RR binding assay and modifying inhibitor physicochemical properties. The importance and possible role of the new structural modifications introduced into this inhibitor series is discussed.

  DOI：

  10.1021/jm00018a022
• 作为产物：
  描述：

  (S)-4-异丙基-2-唑烷酮 在 正丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 49.5h， 生成 benzyl 1-[2-oxo-2-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]ethyl]cyclopentane-1-carboxylate
  参考文献：
  名称：

  Peptidomimetic inhibitors of herpes simplex virus ribonucleotide reductase: a new class of antiviral agents

  摘要：

  We have been investigating a new class of antiviral compounds effective against herpes simplex virus (HSV) in vitro and in vivo. Antiviral activity results from inhibition of HSV ribonucleotide reductase (RR). The inhibitors are designed as mimics of the RR small subunit C-terminus, a region essential for RR subunit association and consequently enzymatic activity. Inhibition results from specific binding of the inhibitor to the HSV RR large subunit thereby preventing subunit association. This report details the structure-activity studies that lead to the identification of BILD 1263, a potent inhibitor of HSV RR subunit association (IC50, 0.2 nM) that also inhibits the replication of HSV types 1 and 2 in cell culture (EC(50), 3 and 4 mu M) and reduces the severity of HSV-1-induced keratitis in a murine ocular model. The discovery of inhibitors with in vitro antiviral activity results from a combination of improving inhibitor potency in a RR binding assay and modifying inhibitor physicochemical properties. The importance and possible role of the new structural modifications introduced into this inhibitor series is discussed.

  DOI：

  10.1021/jm00018a022