2-butoxy-N-hydroxybenzamide | 31792-00-4

• 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: 2-butoxy-N-hydroxybenzamide
• 英文别名: o-Butoxy-benzhydroxamsaeure；2-Butoxybenzenecarbohydroxamic acid
• CAS: 31792-00-4
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: FKKRLCLPENUECF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-丁氧基苯甲酸 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 20.5h， 以60%的产率得到2-butoxy-N-hydroxybenzamide
  参考文献：
  名称：

  Benzohydroxamic acids as potent and selective anti-HCV agents

  摘要：

  A diverse collection of 40 derivatives of benzohydroxamic acid (BHAs) of various structural groups were synthesized and tested against hepatitis C virus (HCV) in full-genome replicon assay. Some of these compounds demonstrated an exceptional activity, suppressing viral replication at sub-micromolar concentrations. The compounds were inactive against key viral enzymes NS3, and NS5B in vitro assays, suggesting host cell inhibition target(s). The testing results were consistent with metal coordination by the BHAs hydroxamic group in complex with a target(s). Remarkably, this class of compounds did not suppress poliomyelitis virus (PV) propagation in RD cells indicating a specific antiviral activity of BHAs against HCV. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.081

文献信息

• Antimicrobial Activity of Hydroxamic Acids
  作者：JUNICHI HASE、KYOICHI KOBASHI、NOBUO KAWAGUCHI、KIYONORI SAKAMOTO

  DOI：10.1248/cpb.19.363

  日期：——

  o-, m- and p-alkyloxybenzohydroxamic acids were synthesized and subjected to the examination for antibacterial and antifungal activity. All the hydroxamic acids tested were almost ineffective for pathogens examined of Enterobacteriaceae, but some of alkyloxybenzo- and fatty acyl-hydroxamic acid were found to be as highly effective for pathogenic fungi as butyl p-hydroxybenzoate being used as a comparison. The increase of carbon number of p-alkyloxybenzo- and fatty acyl-hydroxamic acid led to the increase in their antifungal activity, reached to the maximum at C6 in alkyloxy moiety and C10 in fatty acyl derivatives, and then the gradual decrease in both series. Considering the inhibitory power of hydroxamic acid on plant and bacterial urease, we discussed the possible correlation between antimicrobial activity and inhibitory powers on urease activity of the compounds.

  o-、m- 和 p-烷氧基苯甲酰羟肟酸被合成并进行了抗菌和抗真菌活性的检测。所有测试的羟肟酸对所检测的肠杆菌科病原体几乎无效，但某些烷氧基苯甲酰和脂肪酸酰基羟肟酸被发现对病原真菌具有与作为比较标准的丁基对羟基苯甲酸酯相当的高效性。随着p-烷氧基苯甲酰和脂肪酸酰基羟肟酸中碳数的增加，其抗真菌活性也随之增强，在烷氧基部分达到C6和脂肪酸酰基衍生物部分达到C10时达到最高，随后在这两系列中逐渐下降。鉴于羟肟酸对植物和细菌脲酶的抑制作用，我们讨论了抗微生物活性与这些化合物对脲酶活性抑制能力之间可能的相关性。
• Benzohydroxamic acids as potent and selective anti-HCV agents
  作者：Maxim V. Kozlov、Alla A. Kleymenova、Lyudmila I. Romanova、Konstantin A. Konduktorov、Olga A. Smirnova、Vladimir S. Prasolov、Sergey N. Kochetkov

  DOI：10.1016/j.bmcl.2013.08.081

  日期：2013.11

  A diverse collection of 40 derivatives of benzohydroxamic acid (BHAs) of various structural groups were synthesized and tested against hepatitis C virus (HCV) in full-genome replicon assay. Some of these compounds demonstrated an exceptional activity, suppressing viral replication at sub-micromolar concentrations. The compounds were inactive against key viral enzymes NS3, and NS5B in vitro assays, suggesting host cell inhibition target(s). The testing results were consistent with metal coordination by the BHAs hydroxamic group in complex with a target(s). Remarkably, this class of compounds did not suppress poliomyelitis virus (PV) propagation in RD cells indicating a specific antiviral activity of BHAs against HCV. (C) 2013 Elsevier Ltd. All rights reserved.