(E)-5-(4-O-(4-trifluoromethylphenyl)carbamoyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 9-oxime-11,12-cyclic-carbonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-(4-O-(4-trifluoromethylphenyl)carbamoyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 9-oxime-11,12-cyclic-carbonate
• 英文别名: [(2R,3S,4R,5R,6S)-4-(dimethylamino)-6-[[(1R,2R,5R,7R,8R,9S,11R,12E,13S,14R)-2-ethyl-12-hydroxyimino-9-methoxy-1,5,7,9,11,13-hexamethyl-4,6,16-trioxo-3,15,17-trioxabicyclo[12.3.0]heptadecan-8-yl]oxy]-5-hydroxy-2-methyloxan-3-yl] N-[4-(trifluoromethyl)phenyl]carbamate
• 化学式: C₃₉H₅₆F₃N₃O₁₃
• 分子量: 831.881
• InChiKey: HHFOSUMOAUYJJT-DBLBHWASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  58
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  201
• 氢给体数：
  3
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  克拉霉素 在 吡啶 、 盐酸 、 甲醇 、 草酰氯 、 三氟甲磺酸三甲基硅酯 、 盐酸羟胺 、 sodium acetate 、 三乙胺 、 丙酮 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 55.33h， 生成 (E)-5-(4-O-(4-trifluoromethylphenyl)carbamoyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 9-oxime-11,12-cyclic-carbonate
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel modified 5-O-mycaminose 14-membered ketolides

  摘要：

  A practicable method of introducing a side chain to the C-4' position of 5-O-desosamine in the 14membered ketolides was developed. And using this method, a series of novel modified 5-O-mycaminose ketolides were synthesized. These ketolides containing 5-O-4'-carbamate mycaminose were evaluated for their in vitro antibacterial activities against some respiratory pathogens. 15b and 18e showed comparable activity to telithromycin and clarithromycin. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.023

文献信息

• Synthesis and antibacterial activity of novel modified 5-O-mycaminose 14-membered ketolides
  作者：Yanpeng Xu、Xiaozhuo Chen、Di Zhu、Yi Liu、Zhehui Zhao、Longlong Jin、Chao Liu、Pingsheng Lei

  DOI：10.1016/j.ejmech.2013.08.023

  日期：2013.11

  A practicable method of introducing a side chain to the C-4' position of 5-O-desosamine in the 14membered ketolides was developed. And using this method, a series of novel modified 5-O-mycaminose ketolides were synthesized. These ketolides containing 5-O-4'-carbamate mycaminose were evaluated for their in vitro antibacterial activities against some respiratory pathogens. 15b and 18e showed comparable activity to telithromycin and clarithromycin. (C) 2013 Elsevier Masson SAS. All rights reserved.