(3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-2,3-dimethylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureido-4(1H)-pyrimidone | 468071-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-2,3-dimethylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureido-4(1H)-pyrimidone
• CAS: 468071-35-4
• 化学式: C₃₉H₄₇N₉O₉
• 分子量: 785.857
• InChiKey: QJEALVWBAUBLJB-FSRLHOSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  57.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  226.66
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-2,3-dimethylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureido-4(1H)-pyrimidone 在 氢气 、 palladium dichloride 作用下， 以 甲醇 为溶剂， 以90%的产率得到(3'S,5RS)-5-[N-[3-amino-6-[1,2-dimethylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureidopyrimid-4(1H)-one dihydrochloride
  参考文献：
  名称：

  Novel Antibiotics for the Treatment of Gram-Positive Bacterial Infections

  摘要：

  The natural dipeptide antibiotic TAN 1057 A,B displays excellent antibacterial activity against staphylococci including methicillin resistant Staphylococcus aureus. However, the in vitro activity against additional Gram-positive strains, in particular pneumococci and Enterococcus faecalis, proved to be considerably lower. We report the synthesis and pharmacological evaluation of new derivatives of this natural product that displayed increased antibacterial potency against staphylococci and were also active against pneumococci. In particular, the analogues bearing modified beta-homoarginine side chains with methylated guanidine moieties were shown to be significantly more potent than the natural product TAN 1057 A,B.

  DOI：

  10.1021/jm0111191
• 作为产物：
  描述：

  N^β,N^ω,N^ω'-tris(benzyloxycarbonyl)-N^ε-methyl-(S)-β-homoarginine tert-butyl ester 在 三乙基硅烷 、 四丁基溴化铵 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 54.0h， 生成 (3'S,5RS)-5-[N-[3-benzyloxycarbonylamino-6-[2,3-di(benzyloxycarbonyl)-2,3-dimethylguanidin-1-yl]hexanoyl]-N-methylamino]-5,6-dihydro-2-ureido-4(1H)-pyrimidone
  参考文献：
  名称：

  Novel Antibiotics for the Treatment of Gram-Positive Bacterial Infections

  摘要：

  The natural dipeptide antibiotic TAN 1057 A,B displays excellent antibacterial activity against staphylococci including methicillin resistant Staphylococcus aureus. However, the in vitro activity against additional Gram-positive strains, in particular pneumococci and Enterococcus faecalis, proved to be considerably lower. We report the synthesis and pharmacological evaluation of new derivatives of this natural product that displayed increased antibacterial potency against staphylococci and were also active against pneumococci. In particular, the analogues bearing modified beta-homoarginine side chains with methylated guanidine moieties were shown to be significantly more potent than the natural product TAN 1057 A,B.

  DOI：

  10.1021/jm0111191