(Z)-4-((3-(3-(hexyloxy)phenyl)propyl)amino)-2-hydroxy-4-oxobut-2-enoic acid | 1370459-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-4-((3-(3-(hexyloxy)phenyl)propyl)amino)-2-hydroxy-4-oxobut-2-enoic acid
• 英文别名: (2z)-4-({3-[3-(Hexyloxy)phenyl]propyl}amino)-2-Hydroxy-4-Oxobut-2-Enoic Acid；(Z)-4-[3-(3-hexoxyphenyl)propylamino]-2-hydroxy-4-oxobut-2-enoic acid
• CAS: 1370459-38-3
• 化学式: C₁₉H₂₇NO₅
• 分子量: 349.427
• InChiKey: LTXZSLKTHFHDTP-VKAVYKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(3-Hexoxyphenyl)propan-1-amine 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (Z)-4-((3-(3-(hexyloxy)phenyl)propyl)amino)-2-hydroxy-4-oxobut-2-enoic acid
  参考文献：
  名称：

  HIV-1 Integrase Inhibitor-Inspired Antibacterials Targeting Isoprenoid Biosynthesis

  摘要：

  We report the discovery of antibacterial leads, keto- and diketo-acids, targeting two prenyl transferases: undecaprenyl diphosphate synthase (UPPS) and dehydrosqualene synthase (CrtM). The leads were suggested by the observation that keto- and diketo-acids bind to the active site Mg2+/Asp domain in HIV-1 integrase, and similar domains are present in prenyl transferases. We report the X-ray crystallographic structures of one diketo-acid and one keto-acid bound to CrtM, which supports the Mg2+ binding hypothesis, together with the X-ray structure of one diketo-acid bound to UPPS. In all cases, the inhibitors bind to a farnesyl diphosphate substrate-binding site. Compound 45 had cell growth inhibition MIC90 values of similar to 250-500 ng/mL against Staphylococcus aureus, 500 ng/mL against Bacillus anthracis, 4 mu g/mL against Listeria monocytogenes and Enterococcus faecium, and 1 mu g/mL against Streptococcus pyogenes M1 but very little activity against Escherichia coli (DH5 alpha, K12) or human cell lines.

  DOI：

  10.1021/ml300038t

文献信息

• HIV-1 Integrase Inhibitor-Inspired Antibacterials Targeting Isoprenoid Biosynthesis
  作者：Yonghui Zhang、Fu-Yang Lin、Kai Li、Wei Zhu、Yi-Liang Liu、Rong Cao、Ran Pang、Eunhae Lee、Jordan Axelson、Mary Hensler、Ke Wang、Katie J. Molohon、Yang Wang、Douglas A. Mitchell、Victor Nizet、Eric Oldfield

  DOI：10.1021/ml300038t

  日期：2012.5.10

  We report the discovery of antibacterial leads, keto- and diketo-acids, targeting two prenyl transferases: undecaprenyl diphosphate synthase (UPPS) and dehydrosqualene synthase (CrtM). The leads were suggested by the observation that keto- and diketo-acids bind to the active site Mg2+/Asp domain in HIV-1 integrase, and similar domains are present in prenyl transferases. We report the X-ray crystallographic structures of one diketo-acid and one keto-acid bound to CrtM, which supports the Mg2+ binding hypothesis, together with the X-ray structure of one diketo-acid bound to UPPS. In all cases, the inhibitors bind to a farnesyl diphosphate substrate-binding site. Compound 45 had cell growth inhibition MIC90 values of similar to 250-500 ng/mL against Staphylococcus aureus, 500 ng/mL against Bacillus anthracis, 4 mu g/mL against Listeria monocytogenes and Enterococcus faecium, and 1 mu g/mL against Streptococcus pyogenes M1 but very little activity against Escherichia coli (DH5 alpha, K12) or human cell lines.