(6R,7R,13S,16S,19S,21aS)-16-Benzyloxymethyl-19-((R)-sec-butyl)-7-hexyl-13-((S)-1-hydroxy-ethyl)-6-methyl-tetradecahydro-8-oxa-4a,11,14,17,20-pentaaza-benzocyclononadecene-5,9,12,15,18,21-hexaone | 694528-15-9

• 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: (6R,7R,13S,16S,19S,21aS)-16-Benzyloxymethyl-19-((R)-sec-butyl)-7-hexyl-13-((S)-1-hydroxy-ethyl)-6-methyl-tetradecahydro-8-oxa-4a,11,14,17,20-pentaaza-benzocyclononadecene-5,9,12,15,18,21-hexaone
• CAS: 694528-15-9
• 化学式: C₃₈H₅₉N₅O₉
• 分子量: 729.915
• InChiKey: NRIGWHHOXBYGHH-UPBCXAFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  52.0
• 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：

  (6R,7R,13S,16S,19S,21aS)-16-Benzyloxymethyl-19-((R)-sec-butyl)-7-hexyl-13-((S)-1-hydroxy-ethyl)-6-methyl-tetradecahydro-8-oxa-4a,11,14,17,20-pentaaza-benzocyclononadecene-5,9,12,15,18,21-hexaone 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以89%的产率得到(6R,7R,13S,16S,19S,21aS)-19-((R)-sec-Butyl)-7-hexyl-13-((S)-1-hydroxy-ethyl)-16-hydroxymethyl-6-methyl-tetradecahydro-8-oxa-4a,11,14,17,20-pentaaza-benzocyclononadecene-5,9,12,15,18,21-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-hydroxy-2-methylnonanoyl)-L-homo-Pro-L-allo-Ile-L-Ser(Bn)-OAllyl 在 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 、 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 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 (6R,7R,13S,16S,19S,21aS)-16-Benzyloxymethyl-19-((R)-sec-butyl)-7-hexyl-13-((S)-1-hydroxy-ethyl)-6-methyl-tetradecahydro-8-oxa-4a,11,14,17,20-pentaaza-benzocyclononadecene-5,9,12,15,18,21-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