(Z)-5-fluoro-2-(imidazol-1-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one oxime | 1119142-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (Z)-5-fluoro-2-(imidazol-1-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one oxime
• 英文别名: (NZ)-N-[5-fluoro-2-(imidazol-1-ylmethyl)-3,4-dihydro-2H-naphthalen-1-ylidene]hydroxylamine
• CAS: 1119142-90-3
• 化学式: C₁₄H₁₄FN₃O
• 分子量: 259.283
• InChiKey: MZPXAEUBZVDKTJ-VKAVYKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-5-fluoro-2-(imidazol-1-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one oxime 、 3-氯苄溴 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 以73%的产率得到(Z)-5-fluoro-2-(imidazol-1-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one O-(3-chlorobenzyl)oxime
  参考文献：
  名称：

  Tetrahydronaphthyl azole oxime ethers: The conformationally rigid analogues of oxiconazole as antibacterials☆

  摘要：

  A series of novel (Z)- and (E)-2-imidazolo-/triazolo-methyl tetrahydronaphthyl oxime ethers (7-28) were synthesized as conformationally constrained analogues of oxiconazole and evaluated for antifungal and antibacterial activities. Many of these derivatives exhibited potent antibacterial activity and surprisingly none of them was active against fungal strains. The SAR studies showed that imidazole oxime ethers were more active than the corresponding triazole oxime ethers. Imidazole derivatives 8, 11, 12, 15, 18, 19, 21 and 23 exhibited high inhibitory activity with 1.56-0.39 mu g/mL MIC values against Klebsiella pneumoniae, Escherichia coli and Staphylococcus aureus. These compounds represent new structure scaffolds that can be further optimized to give new antibacterial agents with structures significantly different from those of existing classes of antibiotics. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.006
• 作为产物：
  描述：

  5-fluoro-2-imidazol-1-ylmethyl-3,4-dihydro-2H-naphthalen-1-one 在 盐酸羟胺 、 potassium hydrogencarbonate 作用下， 以 乙醇 、 水 为溶剂， 以62%的产率得到(Z)-5-fluoro-2-(imidazol-1-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one oxime
  参考文献：
  名称：

  Tetrahydronaphthyl azole oxime ethers: The conformationally rigid analogues of oxiconazole as antibacterials☆

  摘要：

  A series of novel (Z)- and (E)-2-imidazolo-/triazolo-methyl tetrahydronaphthyl oxime ethers (7-28) were synthesized as conformationally constrained analogues of oxiconazole and evaluated for antifungal and antibacterial activities. Many of these derivatives exhibited potent antibacterial activity and surprisingly none of them was active against fungal strains. The SAR studies showed that imidazole oxime ethers were more active than the corresponding triazole oxime ethers. Imidazole derivatives 8, 11, 12, 15, 18, 19, 21 and 23 exhibited high inhibitory activity with 1.56-0.39 mu g/mL MIC values against Klebsiella pneumoniae, Escherichia coli and Staphylococcus aureus. These compounds represent new structure scaffolds that can be further optimized to give new antibacterial agents with structures significantly different from those of existing classes of antibiotics. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.006

文献信息

• Tetrahydronaphthyl azole oxime ethers: The conformationally rigid analogues of oxiconazole as antibacterials☆
  作者：Kalpana Bhandari、Nagarapu Srinivas、G.B. Shiva Keshava、Praveen K. Shukla

  DOI：10.1016/j.ejmech.2008.01.006

  日期：2009.1

  A series of novel (Z)- and (E)-2-imidazolo-/triazolo-methyl tetrahydronaphthyl oxime ethers (7-28) were synthesized as conformationally constrained analogues of oxiconazole and evaluated for antifungal and antibacterial activities. Many of these derivatives exhibited potent antibacterial activity and surprisingly none of them was active against fungal strains. The SAR studies showed that imidazole oxime ethers were more active than the corresponding triazole oxime ethers. Imidazole derivatives 8, 11, 12, 15, 18, 19, 21 and 23 exhibited high inhibitory activity with 1.56-0.39 mu g/mL MIC values against Klebsiella pneumoniae, Escherichia coli and Staphylococcus aureus. These compounds represent new structure scaffolds that can be further optimized to give new antibacterial agents with structures significantly different from those of existing classes of antibiotics. (C) 2008 Elsevier Masson SAS. All rights reserved.