| 412046-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 412046-92-5
• 化学式: C₄₀H₅₅FN₂O₁₁
• 分子量: 758.882
• InChiKey: MYLHMBNBWKWJSV-VNDMEIGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  54.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  156.0
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 (1S,2R,5S,7R,8R,9R,11R,13R,14R)-9-[3-[3-(2-aminopyrimidin-5-yl)-1,2-oxazol-5-yl]prop-2-ynoxy]-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-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
• 作为产物：
  描述：

  在 盐酸 、 N-氯代丁二酰亚胺 、 二甲基硫 、 potassium tert-butylate 、 氨 、 水 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  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 of 2-Fluoro-6-<i>O</i>-propargyl-11,12-carbamate Ketolides. A Novel Class of Antibiotics
  作者：Ly T. Phan、Richard F. Clark、Michael Rupp、Yat Sun Or、Daniel T. W. Chu、Zhenkun Ma

  DOI：10.1021/ol006226o

  日期：2000.9.1

  [GRAPHICS]A novel class of 2-fluoro-6-O-propargyl-11,12-carbamate ketolide derivatives of erythromycin has been synthesized for antibacterial SAR studies. Replacement of the C2-hydrogen by a fluorine atom allows the synthesis of 6-O-propargylic ketones and electron-deficient 6-O-propargylic aromatic derivatives by preventing intramolecular CS-enolate Michael cyclization.