4-n-butoxybenzohydroxamyl chloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-n-butoxybenzohydroxamyl chloride
• 英文别名: (1Z)-4-butoxy-N-hydroxybenzenecarboximidoyl chloride
• 化学式: C₁₁H₁₄ClNO₂
• 分子量: 227.691
• InChiKey: DZKLSBYZIXTTEI-QBFSEMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙炔 、 4-n-butoxybenzohydroxamyl chloride 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.17h， 以57%的产率得到3-(4-Butoxy-phenyl)-isoxazole
  参考文献：
  名称：

  Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors

  摘要：

  In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation of HET0016 was limited by its poor solubility under neutral conditions and instability under acidic conditions. The instability of HET0016 in acidic conditions is due to the N-hydroxyformamidine moiety, which is considered to be essential for the potent and selective activity seen in our previous study. The activity was maintained when the N-hydroxyformamidine moiety was replaced by an imidazole ring (3a; IC50 = 5.7 +/- 1.0 nM), but this was associated with a loss of selectivity for cytochrome P450s (CYPs). However, other azole derivatives such as isoxazole derivative 23 (IC50 value 38 +/- 10 nM) and pyrazole derivative 24 (IC50 value 23 +/- 12 nM) showed potent and selective activities with improved stability.

  DOI：

  10.1021/jm020557k
• 作为产物：
  描述：

  4-丁氧基苯甲醛 在 次氯酸叔丁酯 、 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 17.0h， 生成 4-n-butoxybenzohydroxamyl chloride
  参考文献：
  名称：

  Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors

  摘要：

  In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation of HET0016 was limited by its poor solubility under neutral conditions and instability under acidic conditions. The instability of HET0016 in acidic conditions is due to the N-hydroxyformamidine moiety, which is considered to be essential for the potent and selective activity seen in our previous study. The activity was maintained when the N-hydroxyformamidine moiety was replaced by an imidazole ring (3a; IC50 = 5.7 +/- 1.0 nM), but this was associated with a loss of selectivity for cytochrome P450s (CYPs). However, other azole derivatives such as isoxazole derivative 23 (IC50 value 38 +/- 10 nM) and pyrazole derivative 24 (IC50 value 23 +/- 12 nM) showed potent and selective activities with improved stability.

  DOI：

  10.1021/jm020557k

文献信息

• PEAKE, C. J.;STRICKLAND, J. H., SYNTH. COMMUN., 1986, 16, N 7, 763-765
  作者：PEAKE, C. J.、STRICKLAND, J. H.

  DOI：——

  日期：——
• Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors
  作者：Toshio Nakamura、Masakazu Sato、Hiroyuki Kakinuma、Noriyuki Miyata、Kazuo Taniguchi、Kagumi Bando、Ayumi Koda、Kazuya Kameo

  DOI：10.1021/jm020557k

  日期：2003.12.1

  In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation of HET0016 was limited by its poor solubility under neutral conditions and instability under acidic conditions. The instability of HET0016 in acidic conditions is due to the N-hydroxyformamidine moiety, which is considered to be essential for the potent and selective activity seen in our previous study. The activity was maintained when the N-hydroxyformamidine moiety was replaced by an imidazole ring (3a; IC50 = 5.7 +/- 1.0 nM), but this was associated with a loss of selectivity for cytochrome P450s (CYPs). However, other azole derivatives such as isoxazole derivative 23 (IC50 value 38 +/- 10 nM) and pyrazole derivative 24 (IC50 value 23 +/- 12 nM) showed potent and selective activities with improved stability.