(2R)-N-benzyl-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]butanamide | 1388822-18-1

• 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)-N-benzyl-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]butanamide
• CAS: 1388822-18-1
• 化学式: C₄₉H₇₇NO₁₀
• 分子量: 840.151
• InChiKey: HGHFFKPZUADDOQ-YFSFDPQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  60
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  153
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  salinomycin sodium salt 在 硫酸 、 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， 生成 (2R)-N-benzyl-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]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

• Ester derivatives of salinomycin efficiently eliminate breast cancer cells via ER-stress-induced apoptosis
  作者：Dominika Kuran、Sylwia Flis、Michał Antoszczak、Marlena Piskorek、Adam Huczyński

  DOI：10.1016/j.ejphar.2020.173824

  日期：2021.2

  action of this class of semi-synthetic products against breast cancer cells are very limited. Therefore, in this work, we confirmed the anti-breast cancer activity of SAL, and further investigated the potential of its selected C1 amide and ester analogs to destroy breast cancer cells, including the highly aggressive triple-negative MDA-MB-231 cells. Importantly, SAL esters were found to be more potent

  已经发现聚醚离子载体盐霉素（SAL）可以选择性地靶向乳腺癌细胞，包括那些具有干样表型的细胞。另一方面，发现通过使离子载体的C1羧基衍生化而获得的SAL酰胺和酯具有抗癌特性，同时减少了在标准化学疗法中经常发生的潜在毒性问题。但是，关于这类半合成产物对乳腺癌细胞的活性特别是对它们的作用机理的研究非常有限。因此，在这项工作中，我们证实了SAL的抗乳腺癌活性，并进一步研究了其选定的C1酰胺和酯类似物破坏包括高侵袭性三阴性MDA-MB-231细胞在内的乳腺癌细胞的潜力。重要的是，发现SAL酯比天然结构及其酰胺对应物更有效。我们的数据显示SAL酯衍生物，特别是化合物5和7（SAL的2,2,2-三氟乙基和苯并三唑酯）分别增加p-eIF2α（Ser51）和IRE1α蛋白的水平。此外，观察到DNA损伤指示剂（例如γH2AX蛋白和修饰的鸟嘌呤（8-oxoG））水平提高。这些发现表明，由SAL衍生的最有希望的酯
• 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.