(6-Phenylcarbamoyl-hexyl)-carbamic acid benzyl ester | 824970-10-7

• 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: (6-Phenylcarbamoyl-hexyl)-carbamic acid benzyl ester
• 英文别名: Benzyl (7-anilino-7-oxoheptyl)carbamate；benzyl N-(7-anilino-7-oxoheptyl)carbamate
• CAS: 824970-10-7
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: MMTCKKZNOALSKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-Phenylcarbamoyl-hexyl)-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 Thioacetic acid S-[(6-phenylcarbamoyl-hexylcarbamoyl)-methyl] ester
  参考文献：
  名称：

  Identification of a potent non-hydroxamate histone deacetylase inhibitor by mechanism-based drug design

  摘要：

  In order to find novel non-hydroxamate histone deacetylase (HDAC) inhibitors, we synthesized several suberoylanilide hydroxamic acid (SAHA)-based compounds designed on the basis of the catalytic mechanism of HDACs. Among these compounds, 5b was found to be as potent as SAHA. Kinetic enzyme assays and molecular modeling suggested that the mercaptoacetamide moiety of 5b interacts with the zinc in the active site of HDACs and removes a water molecule from the reactive site of the deacetylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.074
• 作为产物：
  描述：

  辛二酸 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 苯 为溶剂， 生成 (6-Phenylcarbamoyl-hexyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Identification of a potent non-hydroxamate histone deacetylase inhibitor by mechanism-based drug design

  摘要：

  In order to find novel non-hydroxamate histone deacetylase (HDAC) inhibitors, we synthesized several suberoylanilide hydroxamic acid (SAHA)-based compounds designed on the basis of the catalytic mechanism of HDACs. Among these compounds, 5b was found to be as potent as SAHA. Kinetic enzyme assays and molecular modeling suggested that the mercaptoacetamide moiety of 5b interacts with the zinc in the active site of HDACs and removes a water molecule from the reactive site of the deacetylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.074

文献信息

• Copper‐Catalyzed Electrophilic Amidation of Organotrifluoroborates with Use of <i>N</i> ‐Methoxyamides
  作者：Shona Banjo、Eiko Nakasuji、Tatsuhiko Meguro、Takaaki Sato、Noritaka Chida

  DOI：10.1002/chem.201901145

  日期：2019.6.12

  A copper‐catalyzed electrophilic amidation of aryltrifluoroborates with use of N‐methoxyamides is reported. The reaction shows high functional group compatibility derived from two distinct features: 1) the high stability of the N‐methoxyamides and 2) the nonbasic mild conditions in the presence of LiCl. The developed method can also be applied to the synthesis of enamides, which are widely distributed

  据报道，使用N-甲氧基酰胺进行了铜催化的芳基三氟硼酸酯的亲电酰胺化反应。该反应显示出源自两个明显特征的高官能团相容性：1）N-甲氧基酰胺的高稳定性，以及2）在LiCl存在下的非碱性温和条件。所开发的方法还可以用于合成广泛分布于天然产物中的烯酰胺。初步的机理研究表明，第一步是在LiCl的协助下对三氟硼酸芳基酯进行金属转移，生成的芳基铜中间体通过非S N 2氧化添加至N-甲氧基酰胺并随后进行还原消除而提供了苯胺。
• Novel histone deacetylase inhibitors: design, synthesis, enzyme inhibition, and binding mode study of SAHA-Based non-hydroxamates
  作者：Takayoshi Suzuki、Yuki Nagano、Azusa Matsuura、Arihiro Kohara、Shin-ichi Ninomiya、Kohfuku Kohda、Naoki Miyata

  DOI：10.1016/j.bmcl.2003.09.048

  日期：2003.12

  In order to find novel non-hydroxamate histone deacetylase (HDAC) inhibitors, a series of compounds modeled after suberoylanilide hydroxamic acid (SAHA) were designed and synthesized as (i) substrate (acetyl lysine) analogues (compounds 3-7), (ii) analogues bearing various functional groups expected to chelate zinc ion (compounds 8-15), and (iii) analogues bearing nucleophilic functional groups which could bind covalently to HDACs (compounds 16-18). In this series, semicarbazide 8b and bromoacetamides 18b,c were found to be potent HDAC inhibitors for non-hydroxamates. (C) 2003 Elsevier Ltd. All rights reserved.
• Identification of a potent non-hydroxamate histone deacetylase inhibitor by mechanism-based drug design
  作者：Takayoshi Suzuki、Azusa Matsuura、Akiyasu Kouketsu、Hidehiko Nakagawa、Naoki Miyata

  DOI：10.1016/j.bmcl.2004.10.074

  日期：2005.1

  In order to find novel non-hydroxamate histone deacetylase (HDAC) inhibitors, we synthesized several suberoylanilide hydroxamic acid (SAHA)-based compounds designed on the basis of the catalytic mechanism of HDACs. Among these compounds, 5b was found to be as potent as SAHA. Kinetic enzyme assays and molecular modeling suggested that the mercaptoacetamide moiety of 5b interacts with the zinc in the active site of HDACs and removes a water molecule from the reactive site of the deacetylation. (C) 2004 Elsevier Ltd. All rights reserved.