5,5-difluoro-10-(4-(hex-5-yn-1-yloxy)phenyl)-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium | 1202406-11-8

• 英文名称: 5,5-difluoro-10-(4-(hex-5-yn-1-yloxy)phenyl)-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
• CAS: 1202406-11-8
• 化学式: C₂₅H₂₇BF₂N₂O
• 分子量: 420.31
• InChiKey: SOKHNGYUCHOOJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  5,5-difluoro-10-(4-(hex-5-yn-1-yloxy)phenyl)-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium 、 4-azidobenzyl alcohol 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以99%的产率得到5,5-difluoro-10-(4-(4-(1-(4-(hydroxymethyl)phenyl)-1H-1,2,3-triazol-4-yl)butoxy)phenyl)-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
  参考文献：
  名称：

  Design and synthesis of novel histone deacetylase inhibitor derived from nuclear localization signal peptide

  摘要：

  We describe herein the synthesis and characterization of a new class of histone deacetylase (HDAC) inhibitors derived from conjugation of a suberoylanilide hydroxamic acid-like aliphatic-hydroxamate pharmacophore to a nuclear localization signal peptide. We found that these conjugates inhibited the histone deacetylase activities of HDACs 1, 2, 6, and 8 in a manner similar to suberoylanilide hydroxamic acid (SAHA). Notably, compound 7b showed a threefold improvement in HDAC 1/2 inhibition, a threefold increase in HDAC 6 selectivity and a twofold increase in HDAC 8 selectivity when compared to SAHA. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.028
• 作为产物：
  描述：

  2,4-二甲基吡咯 、 4-(hex-5-yn-1-yloxy)benzaldehyde 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以54%的产率得到5,5-difluoro-10-(4-(hex-5-yn-1-yloxy)phenyl)-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
  参考文献：
  名称：

  Design and synthesis of novel histone deacetylase inhibitor derived from nuclear localization signal peptide

  摘要：

  We describe herein the synthesis and characterization of a new class of histone deacetylase (HDAC) inhibitors derived from conjugation of a suberoylanilide hydroxamic acid-like aliphatic-hydroxamate pharmacophore to a nuclear localization signal peptide. We found that these conjugates inhibited the histone deacetylase activities of HDACs 1, 2, 6, and 8 in a manner similar to suberoylanilide hydroxamic acid (SAHA). Notably, compound 7b showed a threefold improvement in HDAC 1/2 inhibition, a threefold increase in HDAC 6 selectivity and a twofold increase in HDAC 8 selectivity when compared to SAHA. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.028