3-O-descladinosyl-3-O-[3-(4-isoquinolyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2-chlorobenzyl)oxime 11,12-cyclic carbonate | 1229236-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-descladinosyl-3-O-[3-(4-isoquinolyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2-chlorobenzyl)oxime 11,12-cyclic carbonate
• 英文别名: (1R,2R,5R,6S,7S,8R,9R,11R,12E,13S,14R)-12-[(2-chlorophenyl)methoxyimino]-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-6-[(E)-3-isoquinolin-4-ylprop-2-enoxy]-9-methoxy-1,5,7,9,11,13-hexamethyl-3,15,17-trioxabicyclo[12.3.0]heptadecane-4,16-dione
• CAS: 1229236-72-9
• 化学式: C₅₀H₆₈ClN₃O₁₁
• 分子量: 922.556
• InChiKey: CPJVIGXVEMDCOM-QAWBYISISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  65
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  C₃₇H₆₁ClN₂O₁₀ 在 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) 、 四丁基溴化铵 、 sodium acetate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.5h， 生成 3-O-descladinosyl-3-O-[3-(4-isoquinolyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2-chlorobenzyl)oxime 11,12-cyclic carbonate
  参考文献：
  名称：

  Structure–activity relationships of novel alkylides: 3-O-Arylalkyl clarithromycin derivatives with improved antibacterial activities

  摘要：

  A series of novel alkylides, possessing 3-O-arylallcyl group instead of 3-O-cladinose, were designed, synthesized and evaluated for in vitro antibacterial activities. The increased potency clearly ranked by the order of 3-O-(3-aryl-2-propargyl), 3-O-(3-aryl-E-prop-2-enyl), 3-O-(3-aryl-propyl), and 3-O-(3-aryl-Z-prop-1-enyl) groups. Some alkylides, exemplified by 7a, 10a, 21, 22, 26, 27 and 33, showed improved activities against inducible MLSB resistance and efflux resistance compared to the second-generation macrolides. Among them, 26 possessed comparable activities against erythromycin-susceptible Staphylococcus aureus, Streptococcus pneumoniae and Streptococcus pyogenes (MICs of 0.016-0.5 mu g/mL). Moreover, 26 displayed dramatically enhanced potency against both efflux resistant and inducibly MLSB resistant strains (MICs of 0.125-0.5 mu g/mL) resistant to clarithromycin and azithromycin (MICs of 1 >254 mu g/mL), independent of methicillin-susceptible and methicillin-resistant phenotypes. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.023