N¹-hydroxy-N⁷-(5-(4-(methylsulfonyl)phenyl)-1,3,4-thiadiazol-2-yl)heptanediamide

• 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: N¹-hydroxy-N⁷-(5-(4-(methylsulfonyl)phenyl)-1,3,4-thiadiazol-2-yl)heptanediamide
• 英文别名: N'-hydroxy-N-[5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-yl]heptanediamide
• 化学式: C₁₆H₂₀N₄O₅S₂
• 分子量: 412.491
• InChiKey: UGMGJYAYVYWMCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  175
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-甲砜基苯甲酸 在 盐酸羟胺 、 三乙胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 N¹-hydroxy-N⁷-(5-(4-(methylsulfonyl)phenyl)-1,3,4-thiadiazol-2-yl)heptanediamide
  参考文献：
  名称：

  Improved antiproliferative activity of 1,3,4-thiadiazole-containing histone deacetylase (HDAC) inhibitors by introduction of the heteroaromatic surface recognition motif

  摘要：

  A series of 1,3,4-thiadiazole-containing hydroxamic acids, in accord with the common pharmacophore of histone deacetylase (HDAC) inhibitors (a Zn2+ binding moiety-a linker-a surface recognition motif), was identified as submicromolar HDAC inhibitors by our group. In this study, we continued our efforts to develop 1,3,4-thiadiazole bearing hydroxamate analogues by modifying the surface recognition motif. We found that 1,3,4-thiadiazoles having a heteroaromatic substituent showed better HDAC inhibitory activity in enzymatic assay and higher antiproliferative potency in cellular assay compared to SAHA. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.039

文献信息

• Improved antiproliferative activity of 1,3,4-thiadiazole-containing histone deacetylase (HDAC) inhibitors by introduction of the heteroaromatic surface recognition motif
  作者：Peng Guan、Lei Wang、Xuben Hou、Yichao Wan、Wenfang Xu、Weiping Tang、Hao Fang

  DOI：10.1016/j.bmc.2014.09.039

  日期：2014.11

  A series of 1,3,4-thiadiazole-containing hydroxamic acids, in accord with the common pharmacophore of histone deacetylase (HDAC) inhibitors (a Zn2+ binding moiety-a linker-a surface recognition motif), was identified as submicromolar HDAC inhibitors by our group. In this study, we continued our efforts to develop 1,3,4-thiadiazole bearing hydroxamate analogues by modifying the surface recognition motif. We found that 1,3,4-thiadiazoles having a heteroaromatic substituent showed better HDAC inhibitory activity in enzymatic assay and higher antiproliferative potency in cellular assay compared to SAHA. (C) 2014 Elsevier Ltd. All rights reserved.