carbonic acid benzyl ester 4-(benzyloxycarbonyl-methyl-amino)-2-(14-ethyl-12,13-dihydroxy-10-hydroxyimino-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4-dioxo-oxacyclotetradec-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester | 860476-70-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: carbonic acid benzyl ester 4-(benzyloxycarbonyl-methyl-amino)-2-(14-ethyl-12,13-dihydroxy-10-hydroxyimino-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4-dioxo-oxacyclotetradec-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS: 860476-70-6
• 化学式: C₄₅H₆₄N₂O₁₄
• 分子量: 857.008
• InChiKey: ZNSXNKFLULGMKJ-GCQKPGHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  61.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  209.18
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  carbonic acid benzyl ester 4-(benzyloxycarbonyl-methyl-amino)-2-(14-ethyl-12,13-dihydroxy-10-hydroxyimino-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4-dioxo-oxacyclotetradec-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 在 四(三苯基膦)钯 四氢吡咯 、 吡啶 、 草酰氯 、 水 、 sodium hydride 、 N,N-二甲基甲酰胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 2.25h， 生成
  参考文献：
  名称：

  A new type of ketolide bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether: Synthesis and structure–activity relationships (2)

  摘要：

  A new type of ketolide bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether and its analogues were prepared, and their antibacterial activities and pharmacokinetic properties were evaluated. We found that the introduction of all (R)-alkyl group between the amide and iminoether groups could improve the pharmacokinetic properties while maintaining the activity against erythromycin-resistant Streptococcus pneumoniae. Among the ketolides prepared with the (R)-alkyl group, compound 5p with an N-(3-quinoxalin-6-yl-propyl)-propionamide moiety was found to have in vivo efficacy comparable to CAM with potent in vitro antibacterial activities against the key respiratory pathogens including Haemophilus influenzae and erythromycin-resistant S. pneumoniae. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.036
• 作为产物：
  描述：

  carbonic acid 2-(10-allyloxyimino-14-ethyl-4,12,13-trihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxo-oxacyclotetradec-6-yloxy)-4-(benzyloxycarbonyl-methyl-amino)-6-methyl-tetrahydro-pyran-3-yl ester benzyl ester 在 palladium diacetate 甲酸 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 三氟乙酸酐 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 carbonic acid benzyl ester 4-(benzyloxycarbonyl-methyl-amino)-2-(14-ethyl-12,13-dihydroxy-10-hydroxyimino-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4-dioxo-oxacyclotetradec-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  9-Oxime-3-ketolides: Modification at the C-11,12-diol moiety and antibacterial activities against key respiratory pathogens

  摘要：

  In the search for new types of ketolide antibiotics active against key respiratory pathogens including erythromycin-resistant strains, we conducted an extensive study on the modification at the C-11,12-diol moiety of 9-oxime-3-ketolide derivatives. Among the derivatives prepared, compound 6 with carbonate at the C-11, 12 position was found to have potent antibacterial activities against erythromycin-resistant Staphylococcus aureus as well as other erythromycin-susceptible strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.003