[(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-4,6,12,16-tetraoxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-9-yl] N-[(E)-3-(4-pyrimidin-4-ylphenyl)prop-2-enyl]carbamate | 433922-58-8

• 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-4,6,12,16-tetraoxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-9-yl] N-[(E)-3-(4-pyrimidin-4-ylphenyl)prop-2-enyl]carbamate
• CAS: 433922-58-8
• 化学式: C₄₄H₆₀FN₅O₁₁
• 分子量: 853.986
• InChiKey: TVVNQBPSSMFCSK-MRTJGBIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  61
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  205
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  [(2S,3R,4S,6R)-2-[[(1S,2R,5S,7R,8R,9R,11R,13R,14R)-9-carbamoyloxy-2-ethyl-5-fluoro-1,5,7,9,11,13-hexamethyl-4,6,12,16-tetraoxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-8-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate 在 甲醇 、 三乙基硅烷 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 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-4,6,12,16-tetraoxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-9-yl] N-[(E)-3-(4-pyrimidin-4-ylphenyl)prop-2-enyl]carbamate
  参考文献：
  名称：

  Synthesis and antibacterial activity of C2-fluoro, C6-carbamate ketolides, and their C9-oximes

  摘要：

  Novel C6-carbamate ketolides with C2-fluorination and C9-oximation have been synthesized. The best compounds in this series displayed MIC values of 0.03-0.12 mug/mL against streptococci containing erm and mef resistance determinants and 2-4 mug/mL against Haemophilus influenzae. Several compounds also showed measurable activity against erm(B)-containing enterococci with MIC values of 2-8 mug/mL. In vivo activity was adversely affected by fluorination, possibly as a result of increased serum protein binding. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.067

文献信息

• Synthesis and antibacterial activity of C2-fluoro, C6-carbamate ketolides, and their C9-oximes
  作者：Xiaodong Xu、Todd Henninger、Darren Abbanat、Karen Bush、Barbara Foleno、Jamese Hilliard、Mark Macielag

  DOI：10.1016/j.bmcl.2004.12.067

  日期：2005.2

  Novel C6-carbamate ketolides with C2-fluorination and C9-oximation have been synthesized. The best compounds in this series displayed MIC values of 0.03-0.12 mug/mL against streptococci containing erm and mef resistance determinants and 2-4 mug/mL against Haemophilus influenzae. Several compounds also showed measurable activity against erm(B)-containing enterococci with MIC values of 2-8 mug/mL. In vivo activity was adversely affected by fluorination, possibly as a result of increased serum protein binding. (C) 2005 Elsevier Ltd. All rights reserved.