carbonic acid 2-(14-allyloxyimino-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8-trioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-10-yloxy)-4-(benzyloxycarbonyl-methyl-amino)-6-methyl-tetrahydro-pyran-3-yl ester benzyl ester | 860476-68-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: carbonic acid 2-(14-allyloxyimino-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8-trioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-10-yloxy)-4-(benzyloxycarbonyl-methyl-amino)-6-methyl-tetrahydro-pyran-3-yl ester benzyl ester
• CAS: 860476-68-2
• 化学式: C₄₉H₆₆N₂O₁₅
• 分子量: 923.067
• InChiKey: TWHZTCNGRUIKCP-AAGMZIKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.96
• 重原子数：
  66.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  193.25
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  carbonic acid 2-(14-allyloxyimino-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8-trioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-10-yloxy)-4-(benzyloxycarbonyl-methyl-amino)-6-methyl-tetrahydro-pyran-3-yl ester benzyl ester 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 草酰氯 、 臭氧 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 7.75h， 生成
  参考文献：
  名称：

  A new type of ketolides bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether synthesis and structure–activity relationships

  摘要：

  A new type of ketolides, bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether and a cyclic carbonate at the G 11, 12 position was prepared and the antibacterial activities of the compounds were evaluated. Some of the derivatives showed potent antibacterial activity against both Haemophilus influenzae and Streptococcus pneumoniae, which are clinically important respiratory tract pathogens. Among the derivatives prepared, compound 5s with a quinolin-4-yl moiety was found to have potent and well-balanced activity against S. pneumoniae and H. influenzae including erythromycin-resistant strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.041
• 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 吡啶 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 carbonic acid 2-(14-allyloxyimino-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8-trioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-10-yloxy)-4-(benzyloxycarbonyl-methyl-amino)-6-methyl-tetrahydro-pyran-3-yl ester benzyl 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