N-(4-Fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-2-(tetrahydro-2H-pyran-4-yl)-1,6-dihydropyrimidine-4-carboxamide | 1092544-93-8

• 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: N-(4-Fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-2-(tetrahydro-2H-pyran-4-yl)-1,6-dihydropyrimidine-4-carboxamide
• 英文别名: N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-2-tetrahydropyran-4-yl-pyrimidine-4-carboxamide；N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-(oxan-4-yl)-6-oxopyrimidine-4-carboxamide
• CAS: 1092544-93-8
• 化学式: C₁₈H₂₀FN₃O₄
• 分子量: 361.373
• InChiKey: UWLIRALYPQEHMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氰基四氢吡喃 在 sodium carbonate 、 三乙胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-Fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-2-(tetrahydro-2H-pyran-4-yl)-1,6-dihydropyrimidine-4-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of C2-carbon-linked heterocyclic-5-hydroxy-6-oxo-dihydropyrimidine-4-carboxamides as HIV-1 integrase inhibitors

  摘要：

  Integration of viral DNA into the host cell genome is an obligatory process for successful replication of HIV-1. Integrase catalyzes the insertion of viral DNA into the target DNA and is a validated target for drug discovery. Herein, we report the synthesis, antiviral activity and pharmacokinetic profiles of several C2-carbon-linked heterocyclic pyrimidinone-4-carboxamides that inhibit the strand transfer step of the integration process. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.060

文献信息

• HIV Integrase Inhibitors
  申请人：Naidu B. Narasimhulu

  公开号：US20080306051A1

  公开（公告）日：2008-12-11

  The invention encompasses a series 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.

  该发明涵盖了一系列Formula I的嘧啶酮化合物，可以抑制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。该发明还涵盖了治疗HIV感染者的药物组合物和方法。
• US7763630B2
  申请人：——

  公开号：US7763630B2

  公开（公告）日：2010-07-27
• [EN] HIV INTEGRASE INHIBITORS<br/>[FR] INHIBITEURS DE L'INTÉGRASE DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2008154246A1

  公开（公告）日：2008-12-18

  [EN] The invention encompasses a series 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 the use of the compounds on the manufacture of a medicament for the treatment of those infected with HIV. (I).
  [FR] L'invention concerne une série de composés pyrimidinone représentés par la formule I qui inhibent l'intégrase du VIH et préviennent l'intégration du virus dans l'ADN humain. Cette action rend les composés utiles pour le traitement de l'infection au VIH et du SIDA. L'invention concerne également des compositions pharmaceutiques et l'utilisation des composés dans la fabrication d'un médicament destiné au traitement de patients infectés par le VIH. (I).
• Synthesis and evaluation of C2-carbon-linked heterocyclic-5-hydroxy-6-oxo-dihydropyrimidine-4-carboxamides as HIV-1 integrase inhibitors
  作者：B. Narasimhulu Naidu、Margaret E. Sorenson、Manoj Patel、Yasutsugu Ueda、Jacques Banville、Francis Beaulieu、Sagarika Bollini、Ira B. Dicker、Helen Higley、Zeyu Lin、Lori Pajor、Dawn D. Parker、Brian J. Terry、Ming Zheng、Alain Martel、Nicholas A. Meanwell、Mark Krystal、Michael A. Walker

  DOI：10.1016/j.bmcl.2014.11.060

  日期：2015.2

  Integration of viral DNA into the host cell genome is an obligatory process for successful replication of HIV-1. Integrase catalyzes the insertion of viral DNA into the target DNA and is a validated target for drug discovery. Herein, we report the synthesis, antiviral activity and pharmacokinetic profiles of several C2-carbon-linked heterocyclic pyrimidinone-4-carboxamides that inhibit the strand transfer step of the integration process. (C) 2014 Elsevier Ltd. All rights reserved.