2-tert-Butyl-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid 4-fluoro-benzylamide | 940315-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-tert-Butyl-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid 4-fluoro-benzylamide
• 英文别名: 2-tert-butyl-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-pyrimidine-4-carboxamide；2-tert-butyl-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide
• CAS: 940315-32-2
• 化学式: C₁₇H₂₀FN₃O₃
• 分子量: 333.363
• InChiKey: FTYLDFCKUWPBJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  82
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 5-(benzoyloxy)-2-(tert-butyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate 、 对氟苄胺 以 甲醇 为溶剂， 生成 2-tert-Butyl-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid 4-fluoro-benzylamide
  参考文献：
  名称：

  Development of 2-tbutyl-N-methyl pyrimidones as potent inhibitors of HIV integrase

  摘要：

  A series of novel 2-tbutyl-N-methyl pyrimidone HIV-1 integrase inhibitors have been identified. Optimization of the initial lead resulted in compounds such as 9d and 14a, which showed high levels of activity in cell culture inhibiting viral replication with CIC95 of 10 nM in the presence of 50% normal human serum. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.017

文献信息

• HIV INTEGRASE INHIBITORS
  申请人：Naidu B. Narasimhulu

  公开号：US20070129379A1

  公开（公告）日：2007-06-07

  The invention encompasses a series bicyclic pyrimidinone compounds of Formula I which inhibit HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV.

  这项发明涵盖了一系列公式I的双环嘧啶酮化合物，这些化合物抑制HIV整合酶并防止病毒整合到人类DNA中。这种作用使得这些化合物对治疗HIV感染和艾滋病有用。该发明还涵盖了用于治疗HIV感染者的药物组合物和方法。
• PROCESS FOR PREPARING N-SUBSTITUTED HYDROXYPYRIMIDINONE CARBOXAMIDES
  申请人：Humphrey Guy R.

  公开号：US20100280244A1

  公开（公告）日：2010-11-04

  Processes for preparing certain N-arylalkyl-1-(alkyl or aralkyl)-2-acylaminoalkyl-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamides are disclosed. In one embodiment, the process comprises acylating the free amine in the corresponding N-arylalkyl-1-(alkyl or aralkyl)-2-aminoalkyl-5-ester protected hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide and then deprotecting the 5-hydroxy by base hydrolysis. The hydroxypyrimidinone carboxamide products of the process are HTV integrase inhibitors which are useful for treating HTV infection, treating AIDS, or delaying the onset or progression of AIDS. Certain esterified N-arylalkyl hydroxypyrimidinone carboxamides that can be employed as process intermediates are also disclosed.

  本发明揭示了制备某些N-芳基烷基-1-(烷基或芳基烷基)-2-酰基氨基烷基-5-羟基-6-氧代-1,6-二氢嘧啶-4-羧酰胺的工艺。在一种实施方式中，该工艺包括酰化相应的N-芳基烷基-1-(烷基或芳基烷基)-2-氨基烷基-5-酯保护羟基-6-氧代-1,6-二氢嘧啶-4-羧酰胺中的游离胺，然后通过碱水解去保护5-羟基。该工艺的羟基嘧啶酮羧酰胺产物是HTV整合酶抑制剂，可用于治疗HTV感染、治疗艾滋病或延缓艾滋病的发作或进展。还揭示了可用作工艺中间体的某些酯化的N-芳基烷基羟基嘧啶酮羧酰胺。
• [EN] PYRIMIDINE DERIVATIVES AS HIV INTEGRASE INHIBITORS<br/>[FR] DERIVES DE LA PYRIMIDINE, INHIBITEURS DE L'INTEGRASE DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2007064619A1

  公开（公告）日：2007-06-07

  [EN] The invention encompasses a series bicyclic pyrimidinone compounds of Formula I which inhibit HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV. Formula (I)
  [FR] L'invention porte sur une série de composés bicycliques de pyrimidinone de formule (I) qui inhibent l'intégrase du VIH et empêchent l'intégration du virus à l'ADN humain. Cette action rend ces composés utiles pour traiter les infections par le VIH et le SIDA. L'invention porte également sur des préparations pharmaceutiques et des méthodes de traitement des patients infectés par le VIH.
• Development of 2-tbutyl-N-methyl pyrimidones as potent inhibitors of HIV integrase
  作者：M. Emilia Di Francesco、Paola Pace、Fabrizio Fiore、Francesca Naimo、Fabio Bonelli、Michael Rowley、Vincenzo Summa

  DOI：10.1016/j.bmcl.2008.03.017

  日期：2008.4

  A series of novel 2-tbutyl-N-methyl pyrimidone HIV-1 integrase inhibitors have been identified. Optimization of the initial lead resulted in compounds such as 9d and 14a, which showed high levels of activity in cell culture inhibiting viral replication with CIC95 of 10 nM in the presence of 50% normal human serum. (C) 2008 Elsevier Ltd. All rights reserved.