(E)-3-hydroxy-N'-(1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylidene)-2-naphthohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-3-hydroxy-N'-(1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylidene)-2-naphthohydrazide
• 英文别名: 3-hydroxy-N-[(E)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylideneamino]naphthalene-2-carboxamide
• 化学式: C₂₃H₂₂N₂O₂
• 分子量: 358.44
• InChiKey: APMROBZUPYGXKE-BUVRLJJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-羟基-2-萘甲酸甲酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 (E)-3-hydroxy-N'-(1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylidene)-2-naphthohydrazide
  参考文献：
  名称：

  Exploring naphthyl-carbohydrazides as inhibitors of influenza A viruses

  摘要：

  A library of hydrazide derivatives was synthesized to target non-structural protein 1 of influenza A virus (NS1) as a means to develop anti-influenza drug leads. The lead compound 3-hydroxy-N-[(Z)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylideneamino]naphthalene-2-carboxamide, which we denoted as "HENC", was identified by its ability to increase the melting temperature of the effector domain (ED) of the NS1 protein, as assayed using differential scanning fluorimetry. A library of HENC analogs was tested for inhibitory effect against influenza A virus replication in MDCK cells. A systematic diversification of HENC revealed the identity of the R group attached to the imine carbon atom significantly influenced the antiviral activity. A phenyl or cyclohexyl at this position yielded the most potent antiviral activity. The phenyl containing compound had antiviral activity similar to that of the active form of oseltamivir (Tamiflu), and had no detectable effect on cell viability. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.063

文献信息

• Exploring naphthyl-carbohydrazides as inhibitors of influenza A viruses
  作者：Sanmitra Barman、Lei You、Ran Chen、Vlad Codrea、Grace Kago、Ramakrishna Edupuganti、Jon Robertus、Robert M. Krug、Eric V. Anslyn

  DOI：10.1016/j.ejmech.2013.10.063

  日期：2014.1

  A library of hydrazide derivatives was synthesized to target non-structural protein 1 of influenza A virus (NS1) as a means to develop anti-influenza drug leads. The lead compound 3-hydroxy-N-[(Z)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylideneamino]naphthalene-2-carboxamide, which we denoted as "HENC", was identified by its ability to increase the melting temperature of the effector domain (ED) of the NS1 protein, as assayed using differential scanning fluorimetry. A library of HENC analogs was tested for inhibitory effect against influenza A virus replication in MDCK cells. A systematic diversification of HENC revealed the identity of the R group attached to the imine carbon atom significantly influenced the antiviral activity. A phenyl or cyclohexyl at this position yielded the most potent antiviral activity. The phenyl containing compound had antiviral activity similar to that of the active form of oseltamivir (Tamiflu), and had no detectable effect on cell viability. (C) 2013 Elsevier Masson SAS. All rights reserved.