(5R,6R,12S,15S,18S,20aS)-15-Benzyloxymethyl-18-((R)-sec-butyl)-6-hexyl-12-((S)-1-hydroxy-ethyl)-5-methyl-tetradecahydro-7-oxa-3a,10,13,16,19-pentaaza-cyclopentacyclononadecene-4,8,11,14,17,20-hexaone | 694527-64-5

• 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: (5R,6R,12S,15S,18S,20aS)-15-Benzyloxymethyl-18-((R)-sec-butyl)-6-hexyl-12-((S)-1-hydroxy-ethyl)-5-methyl-tetradecahydro-7-oxa-3a,10,13,16,19-pentaaza-cyclopentacyclononadecene-4,8,11,14,17,20-hexaone
• CAS: 694527-64-5
• 化学式: C₃₇H₅₇N₅O₉
• 分子量: 715.888
• InChiKey: ZYICHZCURYRMCD-RIDDSDSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  192.47
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (5R,6R,12S,15S,18S,20aS)-15-Benzyloxymethyl-18-((R)-sec-butyl)-6-hexyl-12-((S)-1-hydroxy-ethyl)-5-methyl-tetradecahydro-7-oxa-3a,10,13,16,19-pentaaza-cyclopentacyclononadecene-4,8,11,14,17,20-hexaone 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以98%的产率得到(5R,6R,12S,15S,18S,20aS)-18-((R)-sec-Butyl)-6-hexyl-12-((S)-1-hydroxy-ethyl)-15-hydroxymethyl-5-methyl-tetradecahydro-7-oxa-3a,10,13,16,19-pentaaza-cyclopentacyclononadecene-4,8,11,14,17,20-hexaone
  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：

  N-((2R,3R)-3-[Boc-L-allo-Thr(TBS)-GlyO]-2-methylnonanoyl)-L-Pro-L-allo-Ile-L-Ser(Bn)-OAllyl 在 四(三苯基膦)钯 吗啉 、 四丁基氟化铵 、 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 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 (5R,6R,12S,15S,18S,20aS)-15-Benzyloxymethyl-18-((R)-sec-butyl)-6-hexyl-12-((S)-1-hydroxy-ethyl)-5-methyl-tetradecahydro-7-oxa-3a,10,13,16,19-pentaaza-cyclopentacyclononadecene-4,8,11,14,17,20-hexaone
  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