[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-6-yl] (2R)-2-(4-acetamidophenyl)pyrrolidine-1-carboxylate | 1426540-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-6-yl] (2R)-2-(4-acetamidophenyl)pyrrolidine-1-carboxylate
• CAS: 1426540-57-9
• 化学式: C₄₄H₆₈N₄O₁₂
• 分子量: 845.044
• InChiKey: LPYYLMOXOTYMDC-RDDSPYQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  60
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  192
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-6-(2,5-dioxopyrrolidin-1-yl)oxycarbonyloxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-8-yl]oxy]-6-methyloxan-3-yl] acetate 在 甲醇 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 [(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-6-yl] (2R)-2-(4-acetamidophenyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Novel 3-O-carbamoyl erythromycin A derivatives (carbamolides) with activity against resistant staphylococcal and streptococcal isolates

  摘要：

  A novel series of 3-O-carbamoyl erythromycin A derived analogs, labeled carbamolides, with activity versus resistant bacterial isolates of staphylococci (including macrolide and oxazolidinone resistant strains) and streptococci are reported. An (R)-2-aryl substituent on a pyrrolidine carbamate appeared to be critical for achieving potency against resistant strains. Crystal structures showed a distinct aromatic interaction between the (R)-2-aryl (3-pyridyl for 4d) substituent on the pyrrolidine and G2484 (G2505, Escherichia coli) of the Deinococcus radiodurans 50S ribosome (3.2 angstrom resolution). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.067

文献信息

• Novel 3-O-carbamoyl erythromycin A derivatives (carbamolides) with activity against resistant staphylococcal and streptococcal isolates
  作者：Thomas V. Magee、Seungil Han、Sandra P. McCurdy、Thuy-Trinh Nguyen、Karl Granskog、Eric S. Marr、Bruce A. Maguire、Michael D. Huband、Jinshan Michael Chen、Timothy A. Subashi、Veerabahu Shanmugasundaram

  DOI：10.1016/j.bmcl.2013.01.067

  日期：2013.3

  A novel series of 3-O-carbamoyl erythromycin A derived analogs, labeled carbamolides, with activity versus resistant bacterial isolates of staphylococci (including macrolide and oxazolidinone resistant strains) and streptococci are reported. An (R)-2-aryl substituent on a pyrrolidine carbamate appeared to be critical for achieving potency against resistant strains. Crystal structures showed a distinct aromatic interaction between the (R)-2-aryl (3-pyridyl for 4d) substituent on the pyrrolidine and G2484 (G2505, Escherichia coli) of the Deinococcus radiodurans 50S ribosome (3.2 angstrom resolution). (C) 2013 Elsevier Ltd. All rights reserved.