2-(3-chloro-4-fluorobenzyl)-4-(ethylthio)octahydro-1H-4,12a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azocine-1,3,5(2H,12bH)-trione | 1310549-06-4

• 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: 2-(3-chloro-4-fluorobenzyl)-4-(ethylthio)octahydro-1H-4,12a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azocine-1,3,5(2H,12bH)-trione
• CAS: 1310549-06-4
• 化学式: C₂₂H₂₄ClFN₂O₄S
• 分子量: 466.961
• InChiKey: VEVPPHZFUQACHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(3-chloro-4-fluorobenzyl)-4-(ethylthio)octahydro-1H-4,12a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azocine-1,3,5(2H,12bH)-trione 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到2-(3-chloro-4-fluorobenzyl)-4-hydroxy-7,8,9,10,11,12-hexahydropyrrolo[3',4':3,4]pyrido[1,2-a]azocine-1,3,5(2H)-trione
  参考文献：
  名称：

  Development of tricyclic hydroxy-1H-pyrrolopyridine-trione containing HIV-1 integrase inhibitors

  摘要：

  New tricyclic HIV-1 integrase (IN) inhibitors were prepared that combined structural features of bicyclic pyrimidinones with recently disclosed 4,5-dihydroxy-1H-isoindole-1,3(2H)-diones. This combination resulted in the introduction of a nitrogen into the aryl ring and the addition of a fused third ring to our previously described inhibitors. The resulting analogues showed low micromolar inhibitory potency in in vitro HIV-1 integrase assays, with good selectivity for strand transfer relative to 3'-processing. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.03.047
• 作为产物：
  描述：

  1-(2-(ethylthio)acetyl)azocan-2-one 在 sodium periodate 、 乙酸酐 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 3.0h， 生成 2-(3-chloro-4-fluorobenzyl)-4-(ethylthio)octahydro-1H-4,12a-epoxypyrrolo[3',4':3,4]pyrido[1,2-a]azocine-1,3,5(2H,12bH)-trione
  参考文献：
  名称：

  Development of tricyclic hydroxy-1H-pyrrolopyridine-trione containing HIV-1 integrase inhibitors

  摘要：

  New tricyclic HIV-1 integrase (IN) inhibitors were prepared that combined structural features of bicyclic pyrimidinones with recently disclosed 4,5-dihydroxy-1H-isoindole-1,3(2H)-diones. This combination resulted in the introduction of a nitrogen into the aryl ring and the addition of a fused third ring to our previously described inhibitors. The resulting analogues showed low micromolar inhibitory potency in in vitro HIV-1 integrase assays, with good selectivity for strand transfer relative to 3'-processing. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.03.047