(2S,3R,4S,6R)-4-(dimethylamino)-2-(((3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-4-(2-(4-fluorophenyl)acetoxy)-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecan-6-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl benzoate | 1355006-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,6R)-4-(dimethylamino)-2-(((3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-4-(2-(4-fluorophenyl)acetoxy)-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecan-6-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl benzoate
• CAS: 1355006-68-6
• 化学式: C₄₅H₆₄FNO₁₂
• 分子量: 830.001
• InChiKey: DUVJZJFSCGARHG-YVGXEYCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  59.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  167.36
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,6R)-4-(dimethylamino)-2-(((3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-4-(2-(4-fluorophenyl)acetoxy)-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecan-6-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl benzoate 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 生成 (2S,3R,4S,6R)-2-(((3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-4-(2-(4-fluorophenyl)acetoxy)-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecan-6-yl)oxy)-6-methyl-4-(methylamino)tetrahydro-2H-pyran-3-yl benzoate
  参考文献：
  名称：

  Synthesis and antibacterial activity of a novel series of acylides active against community acquired respiratory pathogens

  摘要：

  A novel series of acylides 4 were designed to overcome antibacterial resistance and evaluated for in vitro and in vivo activity. This series of acylides was designed from clarithromycin by changing the substitution on the desosamine nitrogen, followed by conversion to 3-O-acyl and 11,12-carbamate. These compounds showed significantly potent antibacterial activity against not only Gram-positive pathogens, including macrolide-lincosamide-streptogramin B (MLSB)-resistant and efflux-resistant strains, but also Gram-negative pathogens such as Haemophilus influenzae. These acylides also showed better activity against telithromycin resistant Streptococcus pneumoniae strains. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.101
• 作为产物：
  描述：

  克拉霉素 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 32.5h， 生成 (2S,3R,4S,6R)-4-(dimethylamino)-2-(((3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-4-(2-(4-fluorophenyl)acetoxy)-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecan-6-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl benzoate
  参考文献：
  名称：

  Synthesis and antibacterial activity of a novel series of acylides active against community acquired respiratory pathogens

  摘要：

  A novel series of acylides 4 were designed to overcome antibacterial resistance and evaluated for in vitro and in vivo activity. This series of acylides was designed from clarithromycin by changing the substitution on the desosamine nitrogen, followed by conversion to 3-O-acyl and 11,12-carbamate. These compounds showed significantly potent antibacterial activity against not only Gram-positive pathogens, including macrolide-lincosamide-streptogramin B (MLSB)-resistant and efflux-resistant strains, but also Gram-negative pathogens such as Haemophilus influenzae. These acylides also showed better activity against telithromycin resistant Streptococcus pneumoniae strains. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.101