4-((5-(naphthalen-1-ylmethyl)-1,3,4-oxadiazol-2-yl)methyl)benzoic acid | 1618095-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-((5-(naphthalen-1-ylmethyl)-1,3,4-oxadiazol-2-yl)methyl)benzoic acid
• CAS: 1618095-44-5
• 化学式: C₂₁H₁₆N₂O₃
• 分子量: 344.37
• InChiKey: ACPCLFTYSSMLPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76.22
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-((5-(naphthalen-1-ylmethyl)-1,3,4-oxadiazol-2-yl)methyl)benzoic acid 在 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 N-hydroxy-4-((5-(naphthalen-1-ylmethyl)-1,3,4-oxadiazol-2-yl)methyl)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
• 作为产物：
  描述：

  methyl 4-((5-(naphthalen-1-ylmethyl)-1,3,4-oxadiazol-2-yl)methyl)benzoate 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以79%的产率得到4-((5-(naphthalen-1-ylmethyl)-1,3,4-oxadiazol-2-yl)methyl)benzoic acid
  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