5-acetyl-6-methyl-4-phenyl-1-(prop-2-yn-1-yl)-3,4-dihydropyrimidin-2(1H)-one | 1315320-86-5

• 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: 5-acetyl-6-methyl-4-phenyl-1-(prop-2-yn-1-yl)-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 5-Acetyl-4-methyl-6-phenyl-3-prop-2-ynyl-1,6-dihydropyrimidin-2-one；5-acetyl-4-methyl-6-phenyl-3-prop-2-ynyl-1,6-dihydropyrimidin-2-one
• CAS: 1315320-86-5
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: DJMDZUKOEZWJCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-acetyl-6-methyl-4-phenyl-1-(prop-2-yn-1-yl)-3,4-dihydropyrimidin-2(1H)-one 、 1-(氯甲基)-4-硝基苯 在 copper(l) iodide 、 sodium azide 、 三乙胺 作用下， 反应 0.05h， 以98%的产率得到5-acetyl-6-methyl-1-{[1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Dihydropyrimidinone/1,2,3-triazole hybrid molecules: Synthesis and anti-varicella-zoster virus (VZV) evaluation

  摘要：

  By combining the structural features of dihydropyrimidinone and 1,2,3-triazole heterocycles, novel hybrid compounds were synthesized using a simple and convenient method. A series of novel mono and bis 1,2,3-triazole was synthesized via copper-catalyzed Huisgen azide-alkyne cycloadditions (CuAAC) under microwave irradiation. The newly synthesized compounds were evaluated for their antiviral activity against varicella-zoster virus (VZV). Compounds 6aa, lab, 6ba and 6da showed valuable antiviral activities, with EC50 values ranging from 3.6 to 11.3 mu M against TK+ and TK- VZV and without measurable cell-growth inhibition. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.06.028
• 作为产物：
  描述：

  5-乙酰基-6-甲基-4-苯基-3,4-二氢-1H-嘧啶-2-酮 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 1.5h， 生成 5-acetyl-6-methyl-4-phenyl-1-(prop-2-yn-1-yl)-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Pyridopyrimidinone inhibitors of viruses

  摘要：

  本文提供了一种新型小分子吡啶并嘧啶病毒抑制剂，其化学式为（I），例如4-乙酰基-2,3,7,8-四氢-3-苯基吡啶[1,2-f]嘧啶-1-酮，并提供了使用这种化合物制成药物或治疗组合物来抑制和治疗包括正痘病毒和逆转录病毒在内的病毒感染的方法。本文还提供了合成这种化合物的方法。

  公开号：

  US09567331B2

文献信息

• Pyridopyrimidinone inhibitors of viruses
  申请人：Trustees of Boston University

  公开号：US09567331B2

  公开（公告）日：2017-02-14

  Provided herein are novel small molecule pyridomyrimidone viral inhibitor agents of Formula (I), such as 4-acetyl-2,3,7,8-tetrahydro-3-phenylpyrido[1,2-f]pyrimidin-1-one, and methods of using pharmaceutical or therapeutic compositions comprising such viral inhibitor agents of Formula (I) in inhibiting and treating viral infections including orthopox and retroviral infections. Methods of synthesizing such agents are also provided herein.

  本文提供了一种新型小分子吡啶并嘧啶病毒抑制剂，其化学式为（I），例如4-乙酰基-2,3,7,8-四氢-3-苯基吡啶[1,2-f]嘧啶-1-酮，并提供了使用这种化合物制成药物或治疗组合物来抑制和治疗包括正痘病毒和逆转录病毒在内的病毒感染的方法。本文还提供了合成这种化合物的方法。
• Gold Catalyzed Cyclization of Alkyne-Tethered Dihydropyrimidones
  作者：Lauren E. Brown、Peng Dai、John A. Porco、Scott E. Schaus

  DOI：10.1021/ol2015658

  日期：2011.8.19

  Dihydropyrimidones are an important class of biologically active heterocycles accessible from the multicomponent Biginelli condensation. Further manipulation of the dihydropyrimidone skeleton gives access to unique heterocycles. Presented herein is a Au-catalyzed cyclization of alkyne-tethered dihydropyrimidones to yield pyridopyrimidones.
• Dihydropyrimidinone/1,2,3-triazole hybrid molecules: Synthesis and anti-varicella-zoster virus (VZV) evaluation
  作者：Hanane Kaoukabi、Youssef Kabri、Christophe Curti、Moha Taourirte、Juan C. Rodriguez-Ubis、Robert Snoeck、Graciela Andrei、Patrice Vanelle、Hassan B. Lazrek

  DOI：10.1016/j.ejmech.2018.06.028

  日期：2018.7

  By combining the structural features of dihydropyrimidinone and 1,2,3-triazole heterocycles, novel hybrid compounds were synthesized using a simple and convenient method. A series of novel mono and bis 1,2,3-triazole was synthesized via copper-catalyzed Huisgen azide-alkyne cycloadditions (CuAAC) under microwave irradiation. The newly synthesized compounds were evaluated for their antiviral activity against varicella-zoster virus (VZV). Compounds 6aa, lab, 6ba and 6da showed valuable antiviral activities, with EC50 values ranging from 3.6 to 11.3 mu M against TK+ and TK- VZV and without measurable cell-growth inhibition. (C) 2018 Elsevier Masson SAS. All rights reserved.