5-(3,4,6-trideoxy-2-O-acetyl-3-dimethylamino-β-D-xylo-hexopyranosyloxy)-3,6,11,12-tetrahydroxy-9-(2-methoxyethoxy)methoxyimino-2,4,6,8,10,12-hexamethylpentadecan-13-olide | 214902-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(3,4,6-trideoxy-2-O-acetyl-3-dimethylamino-β-D-xylo-hexopyranosyloxy)-3,6,11,12-tetrahydroxy-9-(2-methoxyethoxy)methoxyimino-2,4,6,8,10,12-hexamethylpentadecan-13-olide
• 英文别名: [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-4,7,12,13-tetrahydroxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-2-oxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate
• CAS: 214902-67-7
• 化学式: C₃₅H₆₄N₂O₁₃
• 分子量: 720.899
• InChiKey: AGPMELDULZEQNG-CLNQKJDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  5-(3,4,6-trideoxy-2-O-acetyl-3-dimethylamino-β-D-xylo-hexopyranosyloxy)-3,6,11,12-tetrahydroxy-9-(2-methoxyethoxy)methoxyimino-2,4,6,8,10,12-hexamethylpentadecan-13-olide 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以52%的产率得到(2S,3R,4S,6R)-4-(dimethylamino)-2-(((1R,2R,5R,6S,7R,8S,10R,12R,13R,14R,E)-5-ethyl-1,6,7-trihydroxy-9-(((2-methoxyethoxy)methoxy)imino)-2,6,8,10,12,14-hexamethyl-3-oxo-4,15-dioxabicyclo[10.2.1]pentadecan-13-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Ketolides (6-O-Methyl-3-oxoerythromycin Derivatives):  A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens

  摘要：

  In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called "ketolides". A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.

  DOI：

  10.1021/jm980240d
• 作为产物：
  描述：

  乙酸酐 、 脱克拉定糖罗红霉素 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 以92%的产率得到5-(3,4,6-trideoxy-2-O-acetyl-3-dimethylamino-β-D-xylo-hexopyranosyloxy)-3,6,11,12-tetrahydroxy-9-(2-methoxyethoxy)methoxyimino-2,4,6,8,10,12-hexamethylpentadecan-13-olide
  参考文献：
  名称：

  [EN] MODULATION OF IMMUNE RESPONSES BY ADMINISTRATION OF ROXITHROMYCIN OR ITS DERIVATIVE
  [FR] MODULATION DES RÉPONSES IMMUNES PAR ADMINISTRATION DE ROXITHROMYCINE OU DE SES DÉRIVÉS

  摘要：

  提供的是化合物的公式（III），用于调节免疫反应，包含这些化合物的组合物，以及使用这些组合物治疗涉及免疫反应的疾病或紊乱的方法。在某些实施例中，这些化合物可用于治疗与T细胞和活化T细胞的经内皮迁移以及T细胞和巨噬细胞的促炎细胞因子产生相关的疾病或紊乱。可以治疗的疾病或紊乱包括关节炎和风湿性疾病，如类风湿性关节炎。

  公开号：

  WO2009023196A1