2,3,6,7,8,9-hexahydro[1,4]dioxino[2,3-g]isoquinoline | 52759-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2,3,6,7,8,9-hexahydro[1,4]dioxino[2,3-g]isoquinoline
• 英文别名: 2,3,6,7,8,9-Hexahydro-[1,4]dioxino[2,3-g]isochinolin；2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline
• CAS: 52759-01-0
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD08444666
• 分子量: 191.23
• InChiKey: ZWSHCFDCQSLDIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,6,7,8,9-hexahydro[1,4]dioxino[2,3-g]isoquinoline 、 3-氟-4-甲氧基苄基溴 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以60%的产率得到7-(3-fluoro-4-methoxybenzyl)-2,3,6,7,8,9-hexahydro[1,4]dioxino[2,3-g]isoquinoline
  参考文献：
  名称：

  Studies on Dibenzylamines as Inhibitors of Venezuelan Equine Encephalitis Virus

  摘要：

  Alphaviruses are arthropod-transmitted members of the Togaviridae family that can cause severe disease in humans, including debilitating arthralgia and severe neurological complications. Currently, there are no approved vaccines or antiviral therapies directed against the alphaviruses, and care is limited to treating disease symptoms. A phenotypic cell-based high-throughput screen was performed to identify small molecules that inhibit the replication of Venezuelan Equine Encephalitis Virus (VEEV). The compound, 1-(2,3-dihydrobenzo [b] [1,4] dioxin-6-yl)-N-(3-fluoro-4-methoxybenzyl)ethan-1-amine (1), was identified as a highly active, potent inhibitor of VEEV with an effective concentration for 90% inhibition of virus (EC90) of 0.89 mu M and 7.49 log reduction in virus titers at 10 mu M concentration. These data suggest that further investigation of compound 1 as an antiviral therapeutic against VEEV, and perhaps other alphaviruses, is warranted. Experiments suggested that the antiviral activity of compound 1 is directed at an early step in the VEEV replication cycle by blocking viral RNA and protein synthesis.

  DOI：

  10.1021/acsinfecdis.9b00035
• 作为产物：
  描述：

  2,3,8,9-tetrahydro-[1,4]dioxino[2,3-g]isoquinoline 在 乙醇 、 甲烷 、 钯 作用下， 生成 2,3,6,7,8,9-hexahydro[1,4]dioxino[2,3-g]isoquinoline
  参考文献：
  名称：

  Tomita; Takahashi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 478,479

  摘要：

  DOI：

文献信息

• [EN] BROAD SPECTRUM ANTIVIRAL COMPOSITIONS AND METHODS<br/>[FR] COMPOSITIONS ANTIVIRALES À LARGE SPECTRE ET PROCÉDÉS
  申请人：FORGE LIFE SCIENCE LLC

  公开号：WO2019079519A1

  公开（公告）日：2019-04-25

  Novel thiazole- and isoquinoline- containing compounds are presented that are useful for treating and/or preventing broad-spectrum viral infections. Methods of treating and/or preventing broad-specturm viral infections are also presented. These compounds have shown inhibitio of HCMV, influenza viruses, Zika virus, BK Virus and RSV replication in cell-based assays.
• Studies on Dibenzylamines as Inhibitors of Venezuelan Equine Encephalitis Virus
  作者：Theresa H. Nguyen、Nicole N. Haese、Nikhil Madadi、Sanjay Sarkar、Kiley Bonin、Cassilyn E. Streblow、Sharon Taft-Benz、Nichole A. Tower、Lynn Rasmussen、Robert Bostwick、Corinne E. Augelli-Szafran、Mark J. Suto、Thomas E. Morrison、Victor DeFilippis、Mark T. Heise、Daniel N. Streblow、Ashish K. Pathak

  DOI：10.1021/acsinfecdis.9b00035

  日期：2019.12.13

  Alphaviruses are arthropod-transmitted members of the Togaviridae family that can cause severe disease in humans, including debilitating arthralgia and severe neurological complications. Currently, there are no approved vaccines or antiviral therapies directed against the alphaviruses, and care is limited to treating disease symptoms. A phenotypic cell-based high-throughput screen was performed to identify small molecules that inhibit the replication of Venezuelan Equine Encephalitis Virus (VEEV). The compound, 1-(2,3-dihydrobenzo [b] [1,4] dioxin-6-yl)-N-(3-fluoro-4-methoxybenzyl)ethan-1-amine (1), was identified as a highly active, potent inhibitor of VEEV with an effective concentration for 90% inhibition of virus (EC90) of 0.89 mu M and 7.49 log reduction in virus titers at 10 mu M concentration. These data suggest that further investigation of compound 1 as an antiviral therapeutic against VEEV, and perhaps other alphaviruses, is warranted. Experiments suggested that the antiviral activity of compound 1 is directed at an early step in the VEEV replication cycle by blocking viral RNA and protein synthesis.
• Tomita; Takahashi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 478,479
  作者：Tomita、Takahashi

  DOI：——

  日期：——