N-(6-(2,4-dioxothiazolidin-3-yl)hexyl)benzamide | 1333000-93-3

• 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: N-(6-(2,4-dioxothiazolidin-3-yl)hexyl)benzamide
• 英文别名: N-[6-(2,4-dioxo-1,3-thiazolidin-3-yl)hexyl]benzamide
• CAS: 1333000-93-3
• 化学式: C₁₆H₂₀N₂O₃S
• 分子量: 320.412
• InChiKey: BWZYWMBGIURMSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(6-bromohexyl)-1,3-thiazolidine-2,4-dione 在 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 5.5h， 生成 N-(6-(2,4-dioxothiazolidin-3-yl)hexyl)benzamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 2,4-thiazolidinedione derivatives as histone deacetylase inhibitors targeting liver cancer cell line

  摘要：

  As a part of an ongoing effort to find alternate chemotherapeutic agents for hepatocellular carcinoma, we herein, report the design and synthesis of two novel compounds targeting histone deacetylase (HDAC) with 2,4-thiazolidinedione as zinc chelating group. Further, we demonstrate that these compounds show cytotoxicity that parallels their ability to inhibit HDACs activity in human liver cancer cell line HepG2. The findings obtained in this study indicate that 2,4-thiazolidinedione group may be utilized successfully to inhibit HDAC activity with future potential for lead optimization by chemical derivatization of active compound, N-(6-(2,4-dioxothiazolidin-3- yl)hexyl) benzenesulfonamide.

  DOI：

  10.1007/s00044-011-9623-3

文献信息

• Design, synthesis, and biological evaluation of novel 2,4-thiazolidinedione derivatives as histone deacetylase inhibitors targeting liver cancer cell line
  作者：Rhea Mohan、Ajit K. Sharma、Sanjay Gupta、C. S. Ramaa

  DOI：10.1007/s00044-011-9623-3

  日期：2012.7

  As a part of an ongoing effort to find alternate chemotherapeutic agents for hepatocellular carcinoma, we herein, report the design and synthesis of two novel compounds targeting histone deacetylase (HDAC) with 2,4-thiazolidinedione as zinc chelating group. Further, we demonstrate that these compounds show cytotoxicity that parallels their ability to inhibit HDACs activity in human liver cancer cell line HepG2. The findings obtained in this study indicate that 2,4-thiazolidinedione group may be utilized successfully to inhibit HDAC activity with future potential for lead optimization by chemical derivatization of active compound, N-(6-(2,4-dioxothiazolidin-3- yl)hexyl) benzenesulfonamide.