Methyl 3-(benzylcarbamoyl)benzoate | 925159-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 3-(benzylcarbamoyl)benzoate
• CAS: 925159-45-1
• 化学式: C₁₆H₁₅NO₃
• mdl: MFCD09234636
• 分子量: 269.3
• InChiKey: KOQCVBMLEWCHQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 3-(benzylcarbamoyl)benzoate 在 羟胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 1-N-benzyl-3-N-hydroxybenzene-1,3-dicarboxamide
  参考文献：
  名称：

  Discovery of the First Histone Deacetylase 6/8 Dual Inhibitors

  摘要：

  We disclose the first small molecule histone deacetylase (HDAC) inhibitor (3, BRD73954) capable of potently and selectively inhibiting both HDAC6 and HDAC8 despite the fact that these isoforms belong to distinct phylogenetic classes within the HDAC family of enzymes. Our data demonstrate that meta substituents of phenyl hydroxamic acids are readily accommodated upon binding to HDAC6 and, furthermore, are necessary for the potent inhibition of HDAC8.

  DOI：

  10.1021/jm400390r
• 作为产物：
  描述：

  间苯二甲酸单甲酯 、 苄胺 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 3-(benzylcarbamoyl)benzoate
  参考文献：
  名称：

  Discovery of the First Histone Deacetylase 6/8 Dual Inhibitors

  摘要：

  We disclose the first small molecule histone deacetylase (HDAC) inhibitor (3, BRD73954) capable of potently and selectively inhibiting both HDAC6 and HDAC8 despite the fact that these isoforms belong to distinct phylogenetic classes within the HDAC family of enzymes. Our data demonstrate that meta substituents of phenyl hydroxamic acids are readily accommodated upon binding to HDAC6 and, furthermore, are necessary for the potent inhibition of HDAC8.

  DOI：

  10.1021/jm400390r

文献信息

• Microwave-assisted N-debenzylation of amides with triflic acid
  作者：Frederik Rombouts、Dennis Franken、Carolina Martínez-Lamenca、Mirielle Braeken、Chiara Zavattaro、Jinsheng Chen、Andrés A. Trabanco

  DOI：10.1016/j.tetlet.2010.07.022

  日期：2010.9

  A new and facile microwave-assisted protocol for the debenzylation of N-benzylamides with triflic acid has been developed. Both secondary and tertiary aliphatic or aromatic amides are obtained in moderate to good yields. (C) 2010 Elsevier Ltd. All rights reserved.
• Discovery of the First Histone Deacetylase 6/8 Dual Inhibitors
  作者：David E. Olson、Florence F. Wagner、Taner Kaya、Jennifer P. Gale、Nadia Aidoud、Emeline L. Davoine、Fanny Lazzaro、Michel Weïwer、Yan-Ling Zhang、Edward B. Holson

  DOI：10.1021/jm400390r

  日期：2013.6.13

  We disclose the first small molecule histone deacetylase (HDAC) inhibitor (3, BRD73954) capable of potently and selectively inhibiting both HDAC6 and HDAC8 despite the fact that these isoforms belong to distinct phylogenetic classes within the HDAC family of enzymes. Our data demonstrate that meta substituents of phenyl hydroxamic acids are readily accommodated upon binding to HDAC6 and, furthermore, are necessary for the potent inhibition of HDAC8.