[(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] 5-[3-(4-methylpiperazin-1-yl)propanoylamino]-3-oxo-1H-isoindole-2-carboxylate | 1357104-77-8

• 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: [(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] 5-[3-(4-methylpiperazin-1-yl)propanoylamino]-3-oxo-1H-isoindole-2-carboxylate
• CAS: 1357104-77-8
• 化学式: C₃₇H₅₂N₄O₆
• 分子量: 648.843
• InChiKey: YARUSIJVVXLEEC-QOHQEKJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  47
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-甲基-5-硝基苯甲酸甲酯 在 吡啶 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 tin(II) chloride dihdyrate 、 氨 、 sodium hydride 、 sodium iodide 、 zinc(II) chloride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 四氯化碳 、 乙醇 、 水 为溶剂， 反应 30.0h， 生成 [(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] 5-[3-(4-methylpiperazin-1-yl)propanoylamino]-3-oxo-1H-isoindole-2-carboxylate
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationship studies of conformationally restricted mutilin 14-carbamates

  摘要：

  We report herein the design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates based on the structure of SB-222734. The antibacterial activities of these newly synthesized compounds were also evaluated and compared with linezolid and retapamulin. Results showed that most of the target compounds exhibit good potency in inhibiting the growth of Gram-positive bacteria including Methicillin-susceptible Staphylococcus aureus MSSA (MIC: 0.0625-2 mu g/mL), Methicillin-resistant S. aureus MRSA (MIC: 0.0625-2 mu g/mL), Methicillin-susceptible Staphylococcus epidermidis MSSE (MIC: 0.0625-2 mu g/mL), Methicillin-resistant S. epidermidis MRSE (MIC: 0.0625-2 mu g/mL), and Streptococcus pneumonia (MIC: 0.0625-4 mu g/mL). In particular, three remarkable compounds of this series (12l, 12m, and 21l) exhibited comparable in vitro antibacterial profiles to that of retapamulin. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.063