[(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxo-10-phenylmethoxyimino-4-[(Z)-3-pyrimidin-5-ylprop-1-enoxy]-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate | 1360059-72-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxo-10-phenylmethoxyimino-4-[(Z)-3-pyrimidin-5-ylprop-1-enoxy]-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate
• CAS: 1360059-72-8
• 化学式: C₄₆H₇₀N₄O₁₁
• 分子量: 855.082
• InChiKey: QSTLXZPJDQPWHU-YEORODGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  61
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxo-10-phenylmethoxyimino-4-[(Z)-3-pyrimidin-5-ylprop-1-enoxy]-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate 在 甲醇 作用下， 反应 3.0h， 以16.9%的产率得到3-O-descladinosyl-3-O-[3-(5-pyrimidyl)-(Z)-prop-1-enyl]-6-O-methylerythromycin A 9-(E)-O-benzyl-oxime
  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
• 作为产物：
  描述：

  2',4''-O-bis(trimethylsilyl)erythromycin A 9-(E)-O-benzyloxime 在 盐酸 、 potassium tert-butylate 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 28.67h， 生成 [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxo-10-phenylmethoxyimino-4-[(Z)-3-pyrimidin-5-ylprop-1-enoxy]-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate
  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