3-(3-isopropoxybenzyl)-5-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-one | 1609009-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 3-(3-isopropoxybenzyl)-5-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-one
• 英文别名: 5-methyl-3-[(3-propan-2-yloxyphenyl)methyl]-6H-triazolo[4,5-d]pyrimidin-7-one
• CAS: 1609009-24-6
• 化学式: C₁₅H₁₇N₅O₂
• 分子量: 299.332
• InChiKey: LYDLYEXIHDJWCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3-Propan-2-yloxyphenyl)methyl methanesulfonate 在 sodium azide 、 sodium 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 14.0h， 生成 3-(3-isopropoxybenzyl)-5-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-one
  参考文献：
  名称：

  Identification of [1,2,3]Triazolo[4,5-d]pyrimidin-7(6H)-ones as Novel Inhibitors of Chikungunya Virus Replication

  摘要：

  Chikungunya virus (CHIKV) is a re-emerging Alphavirus that is transmitted to humans by Aedes mosquitoes. Currently, there are still no drugs or vaccines available for the treatment or prevention of this disease. Although traditionally restricted to Africa and Asia, the adaptation of the virus to Aedes albopictus, a mosquito species with an almost worldwide distribution, has contributed to the geographical spread of this virus in the past decade. Here, we report on a new family of compounds named [1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-ones that inhibit CHIKV replication in the low micromolar range with no toxicity to the host (Vero) cells. The most potent compound in this series has an EC50 value below 1 mu M with no cytotoxicity detected up to 668 mu M, therefore affording a selectivity index greater than 600. Interestingly, the compounds have little or no antiviral activity on the replication of other members of the Togaviridae family. The exploration and study of this class of selective inhibitors of CHIKV replication will contribute to deeper insights into the CHIKV life cycle and may be a first step toward the development of a clinical drug candidate.

  DOI：

  10.1021/jm401844c

文献信息

• [EN] NOVEL ANTIVIRAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIVIRAUX
  申请人：UNIV LEUVEN KATH

  公开号：WO2014170368A1

  公开（公告）日：2014-10-23

  The present invention relates to a series of novel compounds and derivatives thereof, methods to prevent or treat viral infections by using the novel compounds, processes for their preparation, their use to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, preferably infections with viruses belonging to the family of the Togaviridae and more preferably infections with chikungunya virus (CHIKV).

  本发明涉及一系列新化合物及其衍生物，利用这些新化合物预防或治疗病毒感染的方法，以及它们的制备过程，用于治疗或预防病毒感染以及用于制造治疗或预防病毒感染的药物，最好是用于治疗属于Togaviridae家族的病毒，更好地是用于治疗寨卡病毒感染。
• Identification of [1,2,3]Triazolo[4,5-<i>d</i>]pyrimidin-7(6<i>H</i>)-ones as Novel Inhibitors of Chikungunya Virus Replication
  作者：Alba Gigante、María-Dolores Canela、Leen Delang、Eva-María Priego、María-José Camarasa、Gilles Querat、Johan Neyts、Pieter Leyssen、María-Jesús Pérez-Pérez

  DOI：10.1021/jm401844c

  日期：2014.5.22

  Chikungunya virus (CHIKV) is a re-emerging Alphavirus that is transmitted to humans by Aedes mosquitoes. Currently, there are still no drugs or vaccines available for the treatment or prevention of this disease. Although traditionally restricted to Africa and Asia, the adaptation of the virus to Aedes albopictus, a mosquito species with an almost worldwide distribution, has contributed to the geographical spread of this virus in the past decade. Here, we report on a new family of compounds named [1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-ones that inhibit CHIKV replication in the low micromolar range with no toxicity to the host (Vero) cells. The most potent compound in this series has an EC50 value below 1 mu M with no cytotoxicity detected up to 668 mu M, therefore affording a selectivity index greater than 600. Interestingly, the compounds have little or no antiviral activity on the replication of other members of the Togaviridae family. The exploration and study of this class of selective inhibitors of CHIKV replication will contribute to deeper insights into the CHIKV life cycle and may be a first step toward the development of a clinical drug candidate.