(2R)-2-[(2R,5S,6R)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,9S,10S,12R,15R)-3-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]-N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]butanamide | 1388822-20-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R)-2-[(2R,5S,6R)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,9S,10S,12R,15R)-3-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]-N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]butanamide
• CAS: 1388822-20-5
• 化学式: C₄₉H₈₅NO₁₃
• 分子量: 896.213
• InChiKey: XGGFQKZVMOXEPW-FOECZUPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  181
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  盐霉素 、 3,6,9-三氧杂-1-氨基癸烷 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 以35%的产率得到(2R)-2-[(2R,5S,6R)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,9S,10S,12R,15R)-3-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]-N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]butanamide
  参考文献：
  名称：

  Synthesis and antimicrobial activity of amide derivatives of polyether antibiotic—salinomycin

  摘要：

  For the first time a direct and practical approach to the synthesis of eight amide derivatives of polyether antibiotic-salinomycin is described. The structure of allyl amide (3a) has been determined using X-ray diffraction. Salinomycin and its amide derivatives have been screened for their in vitro antimicrobial activity against the typical Gram-positive cocci, Gram-negative rods and yeast-like organisms, as well as against a series of clinical isolates of methicillin-resistant Staphylococcus aureus and methicillin-sensitive S. aureus. Amides of salinomycin have been found to show a wide range of activities, from inactive at 256 mu g/mL to active with MIC of 2 mu g/mL, comparable with salinomycin. As a result, phenyl amide (3b) was found to be the most active salinomycin derivative against Gram-positive bacteria, MRSA and MSSA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.081

文献信息

• Synthesis and antimicrobial activity of amide derivatives of polyether antibiotic—salinomycin
  作者：Adam Huczyński、Jan Janczak、Joanna Stefańska、Michał Antoszczak、Bogumil Brzezinski

  DOI：10.1016/j.bmcl.2012.05.081

  日期：2012.7

  For the first time a direct and practical approach to the synthesis of eight amide derivatives of polyether antibiotic-salinomycin is described. The structure of allyl amide (3a) has been determined using X-ray diffraction. Salinomycin and its amide derivatives have been screened for their in vitro antimicrobial activity against the typical Gram-positive cocci, Gram-negative rods and yeast-like organisms, as well as against a series of clinical isolates of methicillin-resistant Staphylococcus aureus and methicillin-sensitive S. aureus. Amides of salinomycin have been found to show a wide range of activities, from inactive at 256 mu g/mL to active with MIC of 2 mu g/mL, comparable with salinomycin. As a result, phenyl amide (3b) was found to be the most active salinomycin derivative against Gram-positive bacteria, MRSA and MSSA. (C) 2012 Elsevier Ltd. All rights reserved.