(2S)-methyl {[2S-3-(tert-butoxycarbonyl-2-methylpropyl)carbamoyl]-5-[3-N-(2,2,4,6,7-pentamethyl-dihydrobenzofran-5-sulfonyl)]}argininate | 1241384-28-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-methyl {[2S-3-(tert-butoxycarbonyl-2-methylpropyl)carbamoyl]-5-[3-N-(2,2,4,6,7-pentamethyl-dihydrobenzofran-5-sulfonyl)]}argininate
• 英文别名: methyl (2S)-5-[[amino-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-[[(2S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]carbamoylamino]pentanoate
• CAS: 1241384-28-0
• 化学式: C₃₀H₄₉N₅O₈S
• 分子量: 639.814
• InChiKey: FWNXSCNFYJNGMU-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  196
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S)-methyl {[2S-3-(tert-butoxycarbonyl-2-methylpropyl)carbamoyl]-5-[3-N-(2,2,4,6,7-pentamethyl-dihydrobenzofran-5-sulfonyl)]}argininate 在 barium hydroxide octahydrate 、 氯化铵 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 4.67h， 生成
  参考文献：
  名称：

  Mechanistic Analysis of Muraymycin Analogues: A Guide to the Design of MraY Inhibitors

  摘要：

  The systematic structure activity relationship (SAX) of the muraymycins (MRYs) using an Ugi four-component reaction (U4CR) was investigated. The impact of the lipophilic substituent on antibacterial activity was significant, and the analogues 8 and 9 having a lipophilic side chain exhibited good activity against a range of Gram-positive bacterial pathogens, including MRSA and VRE. Further investigation of compounds 8 and 9 revealed these analogues to be selective inhibitors of the MraY transferase and nontoxic to HepG2 cells. The SAX of the accessory urea peptide moiety indicated that it could be simplified. Our SAX study of the MRYs suggests a probable mechanism for inhibition of the MraY, where the inner moiety of the urea dipeptide motif interacts with the carbohydrate recognition domain in the cytoplasmic loop S. The predicted binding model would provide further direction toward the design of potent MraY inhibitors. This study has set the stage for the generation of novel antibacterial "lead" compounds based on MRYs.

  DOI：

  10.1021/jm200906r
• 作为产物：
  描述：

  methyl N^ω-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)-L-argininate 、 L-缬氨酸叔丁酯盐酸盐 、 N,N'-羰基二咪唑 以 二氯甲烷 为溶剂， 反应 1.17h， 以63%的产率得到(2S)-methyl {[2S-3-(tert-butoxycarbonyl-2-methylpropyl)carbamoyl]-5-[3-N-(2,2,4,6,7-pentamethyl-dihydrobenzofran-5-sulfonyl)]}argininate
  参考文献：
  名称：

  Mechanistic Analysis of Muraymycin Analogues: A Guide to the Design of MraY Inhibitors

  摘要：

  The systematic structure activity relationship (SAX) of the muraymycins (MRYs) using an Ugi four-component reaction (U4CR) was investigated. The impact of the lipophilic substituent on antibacterial activity was significant, and the analogues 8 and 9 having a lipophilic side chain exhibited good activity against a range of Gram-positive bacterial pathogens, including MRSA and VRE. Further investigation of compounds 8 and 9 revealed these analogues to be selective inhibitors of the MraY transferase and nontoxic to HepG2 cells. The SAX of the accessory urea peptide moiety indicated that it could be simplified. Our SAX study of the MRYs suggests a probable mechanism for inhibition of the MraY, where the inner moiety of the urea dipeptide motif interacts with the carbohydrate recognition domain in the cytoplasmic loop S. The predicted binding model would provide further direction toward the design of potent MraY inhibitors. This study has set the stage for the generation of novel antibacterial "lead" compounds based on MRYs.

  DOI：

  10.1021/jm200906r