7-氨基-N-苯基庚酰胺 | 109127-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 7-氨基-N-苯基庚酰胺
• 英文名称: 7-amino-N-phenylheptanamide
• CAS: 109127-21-1
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: PLCPPAPRLKJLGC-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±28.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-氨基-N-苯基庚酰胺 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 7-(2-mercapto-acetylamino)-heptanoic acid phenylamide
  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 palladium on activated charcoal 二苯基膦叠氮化物 、 氢气 、 三乙胺 作用下， 以 甲醇 、 苯 为溶剂， 生成 7-氨基-N-苯基庚酰胺
  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

• 一种基于伏立诺他骨架的邻氨基苯甲酰胺类化合物及其制备与应用
  申请人：南华大学

  公开号：CN113200885B

  公开（公告）日：2023-01-06

  本发明提供了一种基于伏立诺他骨架的邻氨基苯甲酰胺类化合物及其制备与应用。本发明基于伏立诺他骨架的邻氨基苯甲酰胺类化合物的结构式为，其中，n=1~6；R为甲氨基、二甲氨基、羟基、NH2或。该基于伏立诺他骨架的邻氨基苯甲酰胺类化合物经MTT法测定具有抑制胃癌细胞增殖的作用，可用于制备抗胃癌药物。
• Rational design of metabolically stable HDAC inhibitors: An overhaul of trifluoromethyl ketones
  作者：Banerjee Riddhidev、Karaj Endri、Lamichhane Sabitri、N. Kotsull, Lauren、Kuganesan Nishanth、Isailovic Dragan、Pflum Mary Kay H、Slama James、Taylor William、Tillekeratne L. M. Viranga

  DOI：10.1016/j.ejmech.2022.114807

  日期：2022.12

  regulation of gene expression using histone deacetylase (HDAC) inhibitors is a promising strategy for developing new anticancer agents. The most common HDAC inhibitors are hydroxamates, which, though highly potent, have limitations due to their poor pharmacokinetic properties and lack of isoform selectivity. Trifluoromethylketones (TFMK) developed as alternatives to hydroxamates are rapidly metabolized to inactive

  使用组蛋白脱乙酰酶 (HDAC) 抑制剂对基因表达进行表观遗传调控是开发新型抗癌药物的一种有前景的策略。最常见的 HDAC 抑制剂是异羟肟酸盐，虽然其效力很高，但由于其药代动力学特性较差且缺乏同工型选择性而具有局限性。作为异羟肟酸替代品而开发的三氟甲基酮（TFMK）在体内迅速代谢为无活性的三氟甲醇，这阻碍了它们作为潜在候选药物的进一步发展。为了克服这一限制，我们设计了三氟丙酮酰胺（TFPA）作为 TFMK 替代品。酮羰基旁边额外的吸电子基团的存在使得酮的水合物形式更加稳定，从而防止其在体内代谢还原为醇。此外，这种结构修饰降低了 TFMK 基团作为共价弹头消除脱靶效应的潜力。抑制剂帽基团的额外结构变化使得类似物在细胞毒性测定中的IC 50值范围从高纳摩尔到低微摩尔，并且它们对癌细胞比正常细胞更具选择性。一些最活跃的类似物以低纳摩尔 IC 50值抑制 HDAC 酶，并且被发现对 HDAC8 比
• A critical assessment on stability behaviour of Vorinostat using LC-MS-QTOF with H/D exchange and NMR
  作者：Naveen Chandrasekar、Kalyani Sharma、Sonali Jain、Muktabai Shinde、Girish Patil、Ravi P. Shah

  DOI：10.1016/j.jpba.2023.115687

  日期：2023.11

  degradants were identified as 7-amino-N-phenylheptanamide, 8-hydrazineyl-8-oxo-N-phenyloctanamide, 8-oxo-8-(phenylamino)octanoic acid, 8-oxo-8-(2-(7-oxo-7-(phenylamino)heptyl)hydrazineyl)-N-phenyloctanamide, 8,8′-(1-hydroxyhydrazine-1,2-diyl)bis(8-oxo-N-phenyloctanamide), and N1-((8-oxo-8-(phenylamino)octanoyl)oxy)-N8-phenyloctanediamide. The mechanistic explanation for the formation of each degradant in

  伏立诺他是美国 FDA 批准的第一个用于治疗皮肤 T 细胞淋巴瘤的HDAC 抑制剂。将伏立诺他暴露于 ICH 推荐的水解（酸、碱和中性）、氧化、热和光解应激条件下，以了解降解行为。开发并验证了稳定性指示 LC 方法，用于分离和鉴定强制降解产物。在不同的胁迫条件下，通过 LC-HRMS、MS/MS 和氢-氘交换质量研究鉴定并表征了六种降解物。发现伏立诺他对酸性和碱性环境高度敏感。相反，该药物在热和光解条件下在固态下是稳定的，而当向乙腈-水中溶解状态的伏立诺他提供光解应力时，发现该药物具有适度的稳定性。降解产物被鉴定为7-氨基-N-苯基庚酰胺、8-肼基-8-氧代-N-苯基辛酰胺、8-氧代-8-(苯氨基)辛酸、8-氧代-8-(2-(7-氧代) -7-(苯氨基)庚基)肼基)-N-苯基辛酰胺、8,8′-(1-羟基肼-1,2-二基)双(8-氧代-N-苯基辛酰胺)和N1-((8-氧代) -8-(苯氨基)
• Design, synthesis and biological evaluation of novel o-aminobenzamide derivatives as potential anti-gastric cancer agents in vitro and in vivo
  作者：Yiyue Feng、Yingmei Lu、Junfang Li、Honghua Zhang、Zhao Li、Hanzhong Feng、Xuemei Deng、Dan Liu、Tao Shi、Weifan Jiang、Yongxing He、Jian Zhang、Zhen Wang

  DOI：10.1016/j.ejmech.2021.113888

  日期：2022.1
• 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.