3-O-(benzyl)-N-methylcarbamoyl descladinosylazithromycin-11,12-cyclic carbonate | 1223615-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(benzyl)-N-methylcarbamoyl descladinosylazithromycin-11,12-cyclic carbonate
• 英文别名: 3-O-(benzylcarbamoyl)-3-O-decladinosyl-azithromycin 11,12-carbonate；[(1R,2R,5R,6S,7S,8R,9R,11R,14R,15R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-hydroxy-1,5,7,9,11,13,14-heptamethyl-4,17-dioxo-3,16,18-trioxa-13-azabicyclo[13.3.0]octadecan-6-yl] N-benzylcarbamate
• CAS: 1223615-76-6
• 化学式: C₃₉H₆₃N₃O₁₁
• 分子量: 749.943
• InChiKey: PPXJJCLPNIQZJP-VXRZYPEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  53
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  166
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2'-acetyl-3-O-[1-(1H-imidazol-1-yl)-1-carbonyl]-3-O-descladinose azithromycin-11,12-cyclocarbonate 在 吡啶盐酸盐 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 3-O-(benzyl)-N-methylcarbamoyl descladinosylazithromycin-11,12-cyclic carbonate
  参考文献：
  名称：

  新型3-O-癸二糖基阿奇霉素衍生物的合成和抑菌活性。

  摘要：

  具有2'-O-乙酰基和11,12-环状碳酸酯基，11,12-环状碳酸酯基和11-O-芳基烷基氨基甲酰基侧链以及2'-的3-O-芳基烷基氨基甲酰基descladinosylazithromycin衍生物的新系列。设计，合成了具有11,12-环状碳酸酯基的O-芳基烷基氨基甲酰基descladinosylazithromycin，并通过肉汤微量稀释法对其抗菌活性进行了评估。结果表明，大多数目标化合物对六种易感菌株显示出中等至有利的活性，与对三种表达ermB基因S的肺炎链球菌B1耐药菌株相比，几乎所有目标化合物均显示出显着改善的活性。表达ermB和mefA基因的肺炎链球菌AB11和化脓性链球菌R1。特别是，化合物6h对易感枯草芽孢杆菌ATCC9372（0.5μg/ mL），耐青霉素的表皮葡萄球菌（0.125μg/ mL）和抗红霉素的肺炎链球菌B1（1μg/ mL）和沙门氏菌表现出最强的活性。肺炎AB11（1μg/

  DOI：

  10.1016/j.ejmech.2016.10.065

文献信息

• Synthesis and antibacterial activity of novel 3-O-carbamoyl derivatives of clarithromycin and 11,12-cyclic carbonate azithromycin
  作者：Ling Zhang、Linchen Song、Zhaopeng Liu、Hui Li、Yingdong Lu、Zerong Li、Shutao Ma

  DOI：10.1016/j.ejmech.2009.11.032

  日期：2010.3

  Two series of novel 3-O-carbamoyl derivatives of clarithromycin and 11,12-cyclic carbonate azithromycin were designed, synthesized and evaluated for their in vitro antibacterial activities. Compounds 4j and 4k were the most potent activity against erythromycin-susceptible Staphylococcus aureus, Streptococcus pyogenes and Streptococcus pneumoniae, which were comparable to those of clarithromycin and azithromycin. Compounds 4d, 4h and 4i showed potent activity against erythromycin-resistant S. pneumoniae encoded by the mef gene and compounds 4h and 4i displayed greatly improved activity against erythromycin-resistant S. pneumoniae encoded by the erm gene. Compound 7c exhibited improved activity against erythromycin-resistant S. pneumoniae encoded by the erm and mef genes. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Synthesis and antibacterial activity of novel 3- O -descladinosylazithromycin derivatives
  作者：Mi Yan、Ruixin Ma、Li Jia、Henrietta Venter、Shutao Ma

  DOI：10.1016/j.ejmech.2016.10.065

  日期：2017.2

  256-fold better activity than azithromycin, respectively. Additionally, compounds 6f (0.5 μg/mL) and 6g (0.25 μg/mL) were the most active against S. pneumoniae A22072, which were 8- and 16-fold better activity than azithromycin (4 μg/mL). As for erythromycin-resistant S. pyogenes R1, compound 5a presented the most excellent activity (8 μg/mL), showing 32- and 32-fold higher activity than azithromycin

  具有2'-O-乙酰基和11,12-环状碳酸酯基，11,12-环状碳酸酯基和11-O-芳基烷基氨基甲酰基侧链以及2'-的3-O-芳基烷基氨基甲酰基descladinosylazithromycin衍生物的新系列。设计，合成了具有11,12-环状碳酸酯基的O-芳基烷基氨基甲酰基descladinosylazithromycin，并通过肉汤微量稀释法对其抗菌活性进行了评估。结果表明，大多数目标化合物对六种易感菌株显示出中等至有利的活性，与对三种表达ermB基因S的肺炎链球菌B1耐药菌株相比，几乎所有目标化合物均显示出显着改善的活性。表达ermB和mefA基因的肺炎链球菌AB11和化脓性链球菌R1。特别是，化合物6h对易感枯草芽孢杆菌ATCC9372（0.5μg/ mL），耐青霉素的表皮葡萄球菌（0.125μg/ mL）和抗红霉素的肺炎链球菌B1（1μg/ mL）和沙门氏菌表现出最强的活性。肺炎AB11（1μg/