4-amino-N-[(4-methoxyphenyl)methyl]butanamide;hydrochloride | 1217508-89-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-amino-N-[(4-methoxyphenyl)methyl]butanamide;hydrochloride
• CAS: 1217508-89-8
• 化学式: C₁₂H₁₈N₂O₂*ClH
• 分子量: 258.748
• InChiKey: BFDZIGALVAWQAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,6R)-6-{[(3aR,4R,7R,8S,9S,10R,11R,13R,16R,16aR)-10-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-4-ethyl-11-hydroxy-3a,7,9,11,13,15,16-heptamethyl-2,6-dioxo-tetradecahydro-1H-[1,3]dioxolo[4,5-c]-1-oxa-6-azacyclopentadecan-8-yl]oxy}-4-methoxy-2,4-dimethyloxan-3-yl 1H-imidazole-1-carboxylate 、 4-amino-N-[(4-methoxyphenyl)methyl]butanamide;hydrochloride 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 11,12-cyclic carbonate azithromycin 4″-O-carbamate derivatives

  摘要：

  设计、合成了系列新颖的11,12-环碳酸酯阿奇霉素4'-O-氨基甲酸酯衍生物，并评价了它们的体外抗菌活性。化合物7b和7d对两种红霉素耐药的肺炎链球菌（分别为erm基因和erm及mef基因编码的耐药性）效果最佳（0.5和0.5µg·ml-1）。化合物7a、7e和7g对红霉素敏感菌株（如金黄色葡萄球菌和酿脓链球菌）显示出显著的强大活性。这些结果表明，将延长芳基烷基氨基甲酰基引入C-4"位可显著增强对erm基因或erm和mef基因编码的红霉素耐药细菌的活性。

  DOI：

  10.1038/ja.2009.108
• 作为产物：
  描述：

  tert-butyl N-[4-[(4-methoxyphenyl)methylamino]-4-oxobutyl]carbamate 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 4-amino-N-[(4-methoxyphenyl)methyl]butanamide;hydrochloride
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 11,12-cyclic carbonate azithromycin 4″-O-carbamate derivatives

  摘要：

  设计、合成了系列新颖的11,12-环碳酸酯阿奇霉素4'-O-氨基甲酸酯衍生物，并评价了它们的体外抗菌活性。化合物7b和7d对两种红霉素耐药的肺炎链球菌（分别为erm基因和erm及mef基因编码的耐药性）效果最佳（0.5和0.5µg·ml-1）。化合物7a、7e和7g对红霉素敏感菌株（如金黄色葡萄球菌和酿脓链球菌）显示出显著的强大活性。这些结果表明，将延长芳基烷基氨基甲酰基引入C-4"位可显著增强对erm基因或erm和mef基因编码的红霉素耐药细菌的活性。

  DOI：

  10.1038/ja.2009.108

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.
• Synthesis and antibacterial activity of novel 11,12-cyclic carbonate azithromycin 4″-O-carbamate derivatives
  作者：Chenchen Ma、Zhaopeng Liu、Hualong Song、Rentao Jiang、Fawen He、Shutao Ma

  DOI：10.1038/ja.2009.108

  日期：2010.1

  A series of novel 11,12-cyclic carbonate azithromycin 4″-O-carbamate derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. Compounds 7b and 7d were the most effective (0.5 and 0.5 μg ml−1) against two strains of erythromycin-resistant Streptococcus pneumoniae whose resistance was encoded by the erm gene and the erm and mef genes, respectively. Compounds 7a, 7e and 7g showed significantly potent activity against erythromycin-susceptible strains such as Staphylococcus aureus and S. pyogenes. These results suggest that the introduction of the prolonged arylalkylcarbamoyl group to the C-4″ position can dramatically enhance the activity against erythromycin-resistant bacteria encoded by the erm gene or the erm and mef genes.

  设计、合成了系列新颖的11,12-环碳酸酯阿奇霉素4'-O-氨基甲酸酯衍生物，并评价了它们的体外抗菌活性。化合物7b和7d对两种红霉素耐药的肺炎链球菌（分别为erm基因和erm及mef基因编码的耐药性）效果最佳（0.5和0.5µg·ml-1）。化合物7a、7e和7g对红霉素敏感菌株（如金黄色葡萄球菌和酿脓链球菌）显示出显著的强大活性。这些结果表明，将延长芳基烷基氨基甲酰基引入C-4"位可显著增强对erm基因或erm和mef基因编码的红霉素耐药细菌的活性。