(1S,2R,5S,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-5-fluoro-1,5,7,9,11,13-hexamethyl-9-[3-(3-pyridazin-3-yl-1,2-oxazol-5-yl)prop-2-ynoxy]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone | 865360-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,5S,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-5-fluoro-1,5,7,9,11,13-hexamethyl-9-[3-(3-pyridazin-3-yl-1,2-oxazol-5-yl)prop-2-ynoxy]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
• CAS: 865360-16-3
• 化学式: C₄₀H₅₄FN₅O₁₁
• 分子量: 799.894
• InChiKey: PXQRIOKLJDWFMH-IPSKWSHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  57
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  202
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  3-甲基哒嗪 在 bis-triphenylphosphine-palladium(II) chloride 、 N-氯代丁二酰亚胺 、 potassium tert-butylate 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 55.08h， 生成 (1S,2R,5S,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-5-fluoro-1,5,7,9,11,13-hexamethyl-9-[3-(3-pyridazin-3-yl-1,2-oxazol-5-yl)prop-2-ynoxy]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
  参考文献：
  名称：

  Synthesis and antibacterial activity of 6-O-(heteroaryl-isoxazolyl)propynyl 2-fluoro ketolides

  摘要：

  Macrolide antibiotics are widely prescribed for the treatment of respiratory tract infections; however, the increasing prevalence of macrolide-resistant pathogens is a public health concern. Therefore, the development of new macrolide derivatives with activities against resistant pathogens is urgently needed. A series of novel 6-O-(heteroaryl-isoxazolyl)propynyl 2-fluoro ketolides has been synthesized from erythromycin A. These compounds have shown very promising in vitro and in vivo antibacterial activities against key respiratory pathogens including erythromycin-susceptible/resistant strains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.092

文献信息

• Synthesis and antibacterial activity of 6-O-(heteroaryl-isoxazolyl)propynyl 2-fluoro ketolides
  作者：Tomohiro Sugimoto、Yoichi Shimazaki、Akira Manaka、Tetsuya Tanikawa、Keiko Suzuki、Kayoko Nanaumi、Yoshie Kaneda、Yukiko Yamasaki、Hiroyuki Sugiyama

  DOI：10.1016/j.bmcl.2012.06.092

  日期：2012.9

  Macrolide antibiotics are widely prescribed for the treatment of respiratory tract infections; however, the increasing prevalence of macrolide-resistant pathogens is a public health concern. Therefore, the development of new macrolide derivatives with activities against resistant pathogens is urgently needed. A series of novel 6-O-(heteroaryl-isoxazolyl)propynyl 2-fluoro ketolides has been synthesized from erythromycin A. These compounds have shown very promising in vitro and in vivo antibacterial activities against key respiratory pathogens including erythromycin-susceptible/resistant strains. (C) 2012 Elsevier Ltd. All rights reserved.