2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)propan-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)propan-2-amine
• 英文别名: 2-(2,3-Dihydro-1,4-benzodioxin-6-yl)propan-2-amine
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: YPFDLRYEJXXVQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)propan-2-amine 、 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 12.0h， 以56%的产率得到2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-(3-fluoro-4-methoxybenzyl)propan-2-amine
  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：

  6-乙酰基-1,4-苯并二氧杂环 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、310.27 kPa 条件下， 反应 28.0h， 生成 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)propan-2-amine
  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

文献信息

• Iridium(III)-Catalyzed Benzylic Amine Directed CH Sulfonamidation of Arenes with Sulfonyl Azides
  作者：Heng Chen、Malcolm P. Huestis

  DOI：10.1002/cctc.201402944

  日期：2015.3

  The development of a benzylic amine directed ortho‐sulfonamidation of aryl CH bonds with sulfonyl azides was investigated. The combination of a commercially available iridium(III) complex with a silver salt gave rise to an active manifold capable of promoting efficient CN bond formation for a variety of substrates.

  研究了苄基胺指导的磺酰叠氮化物对芳基CH键的邻位磺酰胺化的研究。商业上可获得的铱（III）配合物与银盐的结合产生了一种活性歧管，该活性歧管能够促进各种底物的有效CN键形成。
• 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.