[(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-[[(2S)-2-aminopropanoyl]amino]-3-oxo-1H-isoindole-2-carboxylate;hydrochloride | 1357104-79-0

• 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-[[(2S)-2-aminopropanoyl]amino]-3-oxo-1H-isoindole-2-carboxylate;hydrochloride
• CAS: 1357104-79-0
• 化学式: C₃₂H₄₃N₃O₆*ClH
• 分子量: 602.171
• InChiKey: VIHSMKGABLQVTR-KZXDOAJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  42
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (3R,3aS,4R,5R,7S,9R,9aR,12R)-5-hydroxy-3-methoxy-4,7,9,12-tetramethyl-7-vinyloctahydro-4,9a-propanocyclopenta[8]annulen-8(9H)-one 在 吡啶 、 盐酸 、 tin(II) chloride dihdyrate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 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-[[(2S)-2-aminopropanoyl]amino]-3-oxo-1H-isoindole-2-carboxylate;hydrochloride
  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

文献信息

• Design, synthesis, and structure–activity relationship studies of conformationally restricted mutilin 14-carbamates
  作者：Liqiang Fu、Xin Liu、Chenyu Ling、Jianjun Cheng、Xingsheng Guo、Huili He、Shi Ding、Yushe Yang

  DOI：10.1016/j.bmcl.2011.12.063

  日期：2012.1

  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.