6-(6-((3-fluorophenyl)amino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N-hydroxyhexanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(6-((3-fluorophenyl)amino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N-hydroxyhexanamide
• 英文别名: 6-[6-(3-fluoroanilino)-1,3-dioxobenzo[de]isoquinolin-2-yl]-N-hydroxyhexanamide
• 化学式: C₂₄H₂₂FN₃O₄
• 分子量: 435.455
• InChiKey: BBHHBNFCYBGQHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  98.7
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 6-(6-bromo-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)hexanoate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1-羟基苯并三唑 、 caesium carbonate 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 异丙醇 、 乙腈 为溶剂， 反应 88.0h， 生成 6-(6-((3-fluorophenyl)amino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N-hydroxyhexanamide
  参考文献：
  名称：

  Highly fluorescent and HDAC6 selective scriptaid analogues

  摘要：

  Fluorescent scriptaid analogues with excellent HDAC6 selectivity (HDAC1/6 > 500) and potency (HDAC6 IC50 < 5 nM) have been synthesised and evaluated. The highly fluorescent nature of the compounds (up to Phi(F)= 0.83 in DMSO and 038 in aqueous buffer) makes them ideally suited for cellular imaging and visualisation of their cytoplasmic localisation was readily accomplished. Whole organism imaging in zebrafish confirmed both the vascular localisation of the new inhibitors and the impact of HDAC6 inhibition on in vivo development. Crown Copyright (C) 2018 Published by Elsevier Masson SAS. All rights reserved,

  DOI：

  10.1016/j.ejmech.2018.11.020

文献信息

• Highly fluorescent and HDAC6 selective scriptaid analogues
  作者：Cassandra L. Fleming、Anthony Natoli、Jeannette Schreuders、Mark Devlin、Prusothman Yoganantharajah、Yann Gibert、Kathryn G. Leslie、Elizabeth J. New、Trent D. Ashton、Frederick M. Pfeffer

  DOI：10.1016/j.ejmech.2018.11.020

  日期：2019.1

  Fluorescent scriptaid analogues with excellent HDAC6 selectivity (HDAC1/6 > 500) and potency (HDAC6 IC50 < 5 nM) have been synthesised and evaluated. The highly fluorescent nature of the compounds (up to Phi(F)= 0.83 in DMSO and 038 in aqueous buffer) makes them ideally suited for cellular imaging and visualisation of their cytoplasmic localisation was readily accomplished. Whole organism imaging in zebrafish confirmed both the vascular localisation of the new inhibitors and the impact of HDAC6 inhibition on in vivo development. Crown Copyright (C) 2018 Published by Elsevier Masson SAS. All rights reserved,