14-O-[(2-chlorobenzamide-2-methylpropane-2-yl)thioacetate] mutilin | 1246738-43-1

• 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: 14-O-[(2-chlorobenzamide-2-methylpropane-2-yl)thioacetate] mutilin
• 英文别名: mutilin 14-O-[1-(2-chloro)benzamide-2-methylpropane-2-yl]thioacetate；(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-Ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl 2-[[2-[(2-chlorobenzoyl)amino]-1,1-dimethylethyl]thio]acetate；[(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[1-[(2-chlorobenzoyl)amino]-2-methylpropan-2-yl]sulfanylacetate
• CAS: 1246738-43-1
• 化学式: C₃₃H₄₆ClNO₅S
• 分子量: 604.251
• InChiKey: LALYLJULHSDFRK-TYFVDVEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  泰妙菌素相关物质A 在 sodium 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 14-O-[(2-chlorobenzamide-2-methylpropane-2-yl)thioacetate] mutilin
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of novel pleuromutilin derivatives

  摘要：

  A series of novel pleuromutilin derivatives possessing thioether moiety has been synthesized via acylation reaction under mild conditions. Their in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis, Escherichia coli, and Streptococcus agalactiae were tested by agar dilution method and Oxford cup assay. Among the 17 compounds screened, 14-O-[(4-methoxybenzamide-2- methylpropane-2-yl) thioacetate] mutilin 4i, 14-O-[(2-aminobenzamide-2-methylpropane-2-yl) thioacetate] mutilin 5a and 14-O-[(4-aminobenzamide-2-methylpropane-2-yl) thioacetate] mutilin 5c were resulted as most active antibacterial agents. Crown Copyright (C) 2013 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.048

文献信息

• Study on the Structure-Activity Relations of Pleuromutilin Derivatives with an Aromatic Amide and a Thioether Group in the C₁₄ side Chain
  作者：Ke-ping Xu、Yuan-yuan Zhang、Juan Luo、Shan-li Chen、Yu-liang Wang

  DOI：10.3184/030823410x12744531851242

  日期：2010.6

  Nine novel pleuromutilin derivatives having benzamide substituents have been synthesised permitting structure-activity relations of pleuromutilin derivatives with aromatic amide and thioether groups in the C₁₄ side chain to be studied. The results showed that the heterocyclic carboxamide group was necessary to enhance bio-activities.

  我们合成了九种带有苯甲酰胺取代基的新型褶菌林衍生物，从而研究了 C14 侧链中带有芳香酰胺和硫醚基团的褶菌林衍生物的结构-活性关系。结果表明，杂环羧酰胺基团是提高生物活性的必要条件。
• Synthesis and antibacterial evaluation of novel pleuromutilin derivatives
  作者：Ruofeng Shang、Yu Liu、Zhijun Xin、Wenzhu Guo、Zhiting Guo、Baocheng Hao、Liang Jianping

  DOI：10.1016/j.ejmech.2013.01.048

  日期：2013.5

  A series of novel pleuromutilin derivatives possessing thioether moiety has been synthesized via acylation reaction under mild conditions. Their in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis, Escherichia coli, and Streptococcus agalactiae were tested by agar dilution method and Oxford cup assay. Among the 17 compounds screened, 14-O-[(4-methoxybenzamide-2- methylpropane-2-yl) thioacetate] mutilin 4i, 14-O-[(2-aminobenzamide-2-methylpropane-2-yl) thioacetate] mutilin 5a and 14-O-[(4-aminobenzamide-2-methylpropane-2-yl) thioacetate] mutilin 5c were resulted as most active antibacterial agents. Crown Copyright (C) 2013 Published by Elsevier Masson SAS. All rights reserved.