7-(2-mercapto-acetylamino)-heptanoic acid phenylamide | 824970-13-0

• 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: 7-(2-mercapto-acetylamino)-heptanoic acid phenylamide
• 英文别名: N-Phenyl-7-(2-sulfanylacetamido)heptanamide；N-phenyl-7-[(2-sulfanylacetyl)amino]heptanamide
• CAS: 824970-13-0
• 化学式: C₁₅H₂₂N₂O₂S
• 分子量: 294.418
• InChiKey: AYGRCXPEUITUKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  59.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  辛二酸 在 palladium on activated charcoal 二苯基膦叠氮化物 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 苯 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

文献信息

• Mercaptoamides as histone deacetylase inhibitors
  申请人：Ahmed Saleh

  公开号：US20060047123A1

  公开（公告）日：2006-03-02

  Mercaptoamide compounds, represented by Formulas (IA), (IB), (IIA), and (IIB): or a pharmaceutically acceptable salt thereof, inhibit histone deacetylase enzyme and are useful for the treatment and/or prevention of various infections, cancerous diseases, and conditions.

  巯基酰胺化合物，以化学式(IA)、(IB)、(IIA)和(IIB)表示，或其药用盐，抑制组蛋白去乙酰化酶，可用于治疗和/或预防各种感染、癌症疾病和疾病。
• [EN] MERCAPTOAMIDES AS HISTONE DEACETYLASE INHIBITORS<br/>[FR] MERCAPTOAMIDES EN TANT QU'INHIBITEURS D'HISTONE DEACETYLASE
  申请人：OSI PHARM INC

  公开号：WO2006028972A2

  公开（公告）日：2006-03-16

  Mercaptoamide compounds, represented by Formulas (IA), (IB), (IIA), and (IIB): or a pharmaceutically acceptable salt thereof, inhibit histone deacetylase enzyme and are useful for the treatment and/or prevention of various infections, cancerous diseases, and conditions.
• 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.