5-chloro-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde | 524005-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 5-chloro-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde
• CAS: 524005-39-8
• 化学式: C₉H₇ClO₃
• 分子量: 198.606
• InChiKey: PQYISUSRKMGKII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  、 5-chloro-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3R)-3-[[4-[(5-chloro-2,3-dihydro-1,4-benzodioxin-6-yl)methylamino]-2-oxabicyclo[2.2.2]octan-1-yl]methyl]-5-fluoro-3-hydroxy-1,7-diazatricyclo[6.3.1.04,12]dodeca-4(12),5,7,9-tetraen-11-one
  参考文献：
  名称：

  Hydroxy tricyclic 1,5-naphthyridinone oxabicyclooctane-linked novel bacterial topoisomerase inhibitors as broad-spectrum antibacterial agents-SAR of RHS moiety (Part-3)

  摘要：

  Novel bacterial topoisomerase inhibitors (NBTIs) are a new class of broad-spectrum antibacterial agents targeting bacterial Gyrase A and ParC and have potential utility in combating antibiotic resistance. (R)-Hydroxy-1,5-naphthyridinone left-hand side (LHS) oxabicyclooctane linked pyridoxazinone right-hand side (RHS) containing NBTIs showed a potent Gram-positive antibacterial profile. SAR around the RHS moiety, including substitutions around pyridooxazinone, pyridodioxane, and phenyl propenoids has been described. A fluoro substituted pyridoxazinone showed an MIC against Staphylococcus aureus of 0.5 mu g/mL with reduced functional hERG activity (IC50 333 mu M) and good in vivo efficacy [ED90 12 mg/kg, intravenous (iv) and 15 mg/kg, oral (p.o.)]. A pyridodioxane-containing NBTI showed a S. aureus MIC of 0.5 mu g/mL, significantly improved hERG IC50 764 mu M and strong efficacy of 11 mg/kg (iv) and 5 mg/kg (p.o.). A phenyl propenoid series of compounds showed potent antibacterial activity, but also showed potent hERG binding activity. Many of the compounds in the hydroxy-tricyclic series showed strong activity against Acinetobacter baumannii, but reduced activity against Escherichia coli and Pseudomonas aeruginosa. Bicyclic heterocycles appeared to be the best RHS moiety for the hydroxy-tricyclic oxabicyclooctane linked NBTIs. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.063