(Z)-2-hydroxy-4-oxo-4-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)amino)but-2-enoic acid | 1370459-63-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-2-hydroxy-4-oxo-4-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)amino)but-2-enoic acid
• CAS: 1370459-63-4
• 化学式: C₁₉H₂₉NO₄
• 分子量: 335.444
• InChiKey: LXCCLGSGOBWSBI-GPZXCRQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  86.63
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (Z)-2-hydroxy-4-oxo-4-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)amino)but-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