ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-methoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate | 868551-49-9

• 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: ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-methoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-methoxy-2-oxoethyl)-[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate；ethyl 4,5-dibromo-1-[(4-fluorophenyl)methyl]-2-[[(2-methoxy-2-oxoethyl)-(4-methylphenyl)sulfonylamino]methyl]pyrrole-3-carboxylate
• CAS: 868551-49-9
• 化学式: C₂₅H₂₅Br₂FN₂O₆S
• 分子量: 660.356
• InChiKey: YQFKHYZHRYZNQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-methoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0 ℃ 、275.8 kPa 条件下， 反应 3.5h， 生成 methyl 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylate
  参考文献：
  名称：

  Design and Synthesis of Novel N-Hydroxy-Dihydronaphthyridinones as Potent and Orally Bioavailable HIV-1 Integrase Inhibitors

  摘要：

  HIV-1 integrase (IN) is one of three enzymes encoded by the HIV genome and is essential for viral replication, and HIV-1 IN inhibitors have emerged as a new promising class of therapeutics. Recently, we reported the synthesis of orally bioavailable azaindole hydroxamic acids that were potent inhibitors of the HIV-1 IN enzyme. Here we disclose the design and synthesis of novel tricyclic N-hydroxy-dihydronaphthyridinones as potent, orally bioavailable HIV-1 integrase inhibitors displaying excellent ligand and lipophilic efficiencies.

  DOI：

  10.1021/jm200208d
• 作为产物：
  描述：

  2-甲基吡咯-3-甲酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 39.0h， 生成 ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-methoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Design and Synthesis of Novel N-Hydroxy-Dihydronaphthyridinones as Potent and Orally Bioavailable HIV-1 Integrase Inhibitors

  摘要：

  HIV-1 integrase (IN) is one of three enzymes encoded by the HIV genome and is essential for viral replication, and HIV-1 IN inhibitors have emerged as a new promising class of therapeutics. Recently, we reported the synthesis of orally bioavailable azaindole hydroxamic acids that were potent inhibitors of the HIV-1 IN enzyme. Here we disclose the design and synthesis of novel tricyclic N-hydroxy-dihydronaphthyridinones as potent, orally bioavailable HIV-1 integrase inhibitors displaying excellent ligand and lipophilic efficiencies.

  DOI：

  10.1021/jm200208d

文献信息

• [EN] INHIBITORS OF THE HIV INTEGRASE ENZYME<br/>[FR] INHIBITEURS DE L'ENZYME INTEGRASE DU VIH
  申请人：PFIZER

  公开号：WO2006027694A1

  公开（公告）日：2006-03-16

  The present invention relates to compounds of formula (I), or a pharmaceutically acceptable salt or solvate thereof, pharmaceutical compositions comprisingm compounds of formula (I), and their methods of use in treating HIV-infected mammals.

  本发明涉及公式(I)的化合物，或其药物可接受的盐或溶剂化物，包含公式(I)化合物的药物组合物，以及它们在治疗HIV感染哺乳动物中的用途方法。
• Inhibitors of the HIV integrase enzyme
  申请人：Dress Ruprecht Klaus

  公开号：US20050277661A1

  公开（公告）日：2005-12-15

  The present invention is directed to compounds of formula (i), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as modulators or inhibitors of the human immunodeficiency virus (“HIV”) integrase enzyme.

  本发明涉及式（i）的化合物及其药学上可接受的盐和溶剂，它们的合成，以及它们作为人类免疫缺陷病毒（“HIV”）整合酶酶的调节剂或抑制剂的用途。
• Inhibitors of the Hiv Integrase Enzyme
  申请人：Dress Ruprecht Klaus

  公开号：US20070232644A1

  公开（公告）日：2007-10-04

  The present invention relates to compounds of formula (I), or a pharmaceutically acceptable salt or solvate thereof, pharmaceutical compositions comprising compounds of formula (I), and their methods of use in treating HIV-infected mammals.

  本发明涉及公式(I)的化合物，或其药学上可接受的盐或溶剂，包括公式(I)的化合物的制药组合物，以及它们在治疗感染HIV的哺乳动物中的使用方法。
• INHIBITORS OF THE HIV INTEGRASE ENZYME
  申请人：Dress Klaus Ruprecht

  公开号：US20100137283A1

  公开（公告）日：2010-06-03

  The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as modulators or inhibitors of the human immunodeficiency virus (“HIV”) integrase enzyme.

  本发明涉及化合物(I)及其药学上可接受的盐和溶剂，其合成以及它们作为人类免疫缺陷病毒（“HIV”）整合酶酶的调节剂或抑制剂的用途。
• [EN] PYRROLOPYRIDINE DERIVATIVES AND THEIR USE AS HIV-INTEGRASE INHIBITORS<br/>[FR] INHIBITEURS DE L'ENZYME INTEGRASE DU VIH
  申请人：PFIZER

  公开号：WO2005103003A3

  公开（公告）日：2006-03-16