4"-O-(((4-methoxybenzyl)amino)-4-oxo-butyl)carbamoylclarithromycin | 1235735-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4"-O-(((4-methoxybenzyl)amino)-4-oxo-butyl)carbamoylclarithromycin
• 英文别名: 4''-O-(((4-methoxybenzyl)amino)-4-oxo-butyl)carbamoylclarithromycin；[(2S,3S,4R,6R)-6-[[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-4-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl] N-[4-[(4-methoxyphenyl)methylamino]-4-oxobutyl]carbamate
• CAS: 1235735-98-4
• 化学式: C₅₁H₈₅N₃O₁₆
• 分子量: 996.246
• InChiKey: OVLRTFBILNBXSU-WHOUBXIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  70
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  239
• 氢给体数：
  5
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  克拉霉素 在 甲醇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 120.0h， 生成 4"-O-(((4-methoxybenzyl)amino)-4-oxo-butyl)carbamoylclarithromycin
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of novel clarithromycin derivatives with C-4″ elongated arylalkyl groups against macrolide-resistant strains

  摘要：

  Novel clarithromycin derivatives with C-4 '' elongated arylalkyl groups were designed, synthesized and evaluated to probe the effect of different lengths of their C-4 '' side chains on the activity against resistant bacterial strains. These derivatives had excellent activity against erythromycin-susceptible Streptococcus pneumoniae, Streptococcus aureus or Streptococcus pyogenes and some of them exhibited greatly improved activity against erythromycin-resistant strains. Compounds 18 and 16, which had the C-4 '' elongated arylalkyl groups with eight atoms from the 4 ''-oxygen atom to the terminal benzene ring, were the most effective against S. pneumoniae expressing the erm gene and the erm and me! genes. In contrast, the most potent compounds 3, 5, 9,17 and 18 against S. pneumoniae expressing the mef gene had C-4 '' elongated arylalkyl groups with three to eight atoms between the 4 ''-oxygen atom and the terminal aromatic ring. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.035

文献信息

• Synthesis and antibacterial activity of novel 4″-O-arylalkylcarbamoyl and 4″-O-((arylalkylamino)-4-oxo-butyl)carbamoyl clarithromycin derivatives
  作者：Yongjing Ju、Ruiqing Xian、Ling Zhang、Ruixin Ma、Jichao Cao、Shutao Ma

  DOI：10.1016/j.bmcl.2010.04.051

  日期：2010.6

  Novel series of novel 4 ''-O-arylalkylcarbamoyl and 4 ''-O-((arylalkylamino)-4-oxo-butyl) carbamoyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These derivatives retained excellent activity against the erythromycin-susceptible strains and showed significantly improved activity against all of the tested erythromycin-resistant strains. Among them, compound 4c was the most effective (0.06 mu g/mL) against Streptococcus pneumonia encoded by the erm gene and compound 4a was had the most potent activity (0.25 mu g/mL) against S. pneumonia encoded by the erm and mef genes. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and antibacterial evaluation of novel clarithromycin derivatives with C-4″ elongated arylalkyl groups against macrolide-resistant strains
  作者：Shutao Ma、Bo Jiao、Yongjing Ju、Manjie Zheng、Ruixin Ma、Lin Liu、Ling Zhang、Xuecui Shen、Chenchen Ma、Ya Meng、Hui Wang、Yunkun Qi、Xiaodong Ma、Wenping Cui

  DOI：10.1016/j.ejmech.2010.11.035

  日期：2011.2

  Novel clarithromycin derivatives with C-4 '' elongated arylalkyl groups were designed, synthesized and evaluated to probe the effect of different lengths of their C-4 '' side chains on the activity against resistant bacterial strains. These derivatives had excellent activity against erythromycin-susceptible Streptococcus pneumoniae, Streptococcus aureus or Streptococcus pyogenes and some of them exhibited greatly improved activity against erythromycin-resistant strains. Compounds 18 and 16, which had the C-4 '' elongated arylalkyl groups with eight atoms from the 4 ''-oxygen atom to the terminal benzene ring, were the most effective against S. pneumoniae expressing the erm gene and the erm and me! genes. In contrast, the most potent compounds 3, 5, 9,17 and 18 against S. pneumoniae expressing the mef gene had C-4 '' elongated arylalkyl groups with three to eight atoms between the 4 ''-oxygen atom and the terminal aromatic ring. (C) 2010 Elsevier Masson SAS. All rights reserved.