8-N-methyl-24-O-benzyl-globomycin | 694528-14-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 8-N-methyl-24-O-benzyl-globomycin
• CAS: 694528-14-8
• 化学式: C₄₀H₆₅N₅O₉
• 分子量: 759.984
• InChiKey: FRZFZHLYHLSDAJ-OXVASHOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  183.68
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  8-N-methyl-24-O-benzyl-globomycin 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以94%的产率得到8-N-methyl-globomycin
  参考文献：
  名称：

  Structure–activity relationships of globomycin analogues as antibiotics

  摘要：

  Globomycin (1a), a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. The hydroxyl group in the L-Ser residue was essential for the antimicrobial activity and the length of the alkyl side chain greatly influenced the activity. In addition, derivatives that had a modified cyclic core exhibited weak activity. One of the analogues showed a wider antimicrobial spectrum, effective against not only Gram-negative but also Gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.055
• 作为产物：
  描述：

  Boc-L-allo-Thr(TBS)-N-Me-Gly-OBn 在 palladium on activated charcoal 、 四(三苯基膦)钯 吗啉 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 8-N-methyl-24-O-benzyl-globomycin
  参考文献：
  名称：

  Structure–activity relationships of globomycin analogues as antibiotics

  摘要：

  Globomycin (1a), a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. The hydroxyl group in the L-Ser residue was essential for the antimicrobial activity and the length of the alkyl side chain greatly influenced the activity. In addition, derivatives that had a modified cyclic core exhibited weak activity. One of the analogues showed a wider antimicrobial spectrum, effective against not only Gram-negative but also Gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.055