N-(2-aminophenyl)-4-(5-(naphthalen-1-ylmethyl)-1,3,4-oxadiazol-2-yl)benzamide | 1618095-33-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-(2-aminophenyl)-4-(5-(naphthalen-1-ylmethyl)-1,3,4-oxadiazol-2-yl)benzamide
• CAS: 1618095-33-2
• 化学式: C₂₈H₂₂N₄O₂
• 分子量: 446.508
• InChiKey: HFZJPVYVYYPCDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  94.04
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  对苯二甲酸单甲酯 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 N-(2-aminophenyl)-4-(5-(naphthalen-1-ylmethyl)-1,3,4-oxadiazol-2-yl)benzamide
  参考文献：
  名称：

  1,3,4-Oxadiazole-Containing Histone Deacetylase Inhibitors: Anticancer Activities in Cancer Cells

  摘要：

  We describe 1,3,4-oxadiazole-containing hydroxamates (2) and 2-aminoanilides (3) as histone deacetylase inhibitors. Among them, 2t, 2x, and 3i were the most potent and selective against HDAC1. In U937 leukemia cells, 2t was more potent than SAHA in inducing apoptosis, and 3i displayed cell differentiation with a potency similar to MS-275. In several acute myeloid leukemia (AML) cell lines, as well as in U937 cells in combination with doxorubicin, 3i showed higher antiproliferative effects than SAHA.

  DOI：

  10.1021/jm500303u

文献信息

• 1,3,4-Oxadiazole-Containing Histone Deacetylase Inhibitors: Anticancer Activities in Cancer Cells
  作者：Sergio Valente、Daniela Trisciuoglio、Teresa De Luca、Angela Nebbioso、Donatella Labella、Alessia Lenoci、Chiara Bigogno、Giulio Dondio、Marco Miceli、Gerald Brosch、Donatella Del Bufalo、Lucia Altucci、Antonello Mai

  DOI：10.1021/jm500303u

  日期：2014.7.24

  We describe 1,3,4-oxadiazole-containing hydroxamates (2) and 2-aminoanilides (3) as histone deacetylase inhibitors. Among them, 2t, 2x, and 3i were the most potent and selective against HDAC1. In U937 leukemia cells, 2t was more potent than SAHA in inducing apoptosis, and 3i displayed cell differentiation with a potency similar to MS-275. In several acute myeloid leukemia (AML) cell lines, as well as in U937 cells in combination with doxorubicin, 3i showed higher antiproliferative effects than SAHA.