4''-O-[3-({2-[(1-cyclopropyl-1,4-dihydro-3-{[(2-hydroxyethyl)amino]carbonyl}-7-chloro-4-oxo-6-quinolyl)amino]ethyl}amino)propanoyl]-9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A | 1350922-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4''-O-[3-({2-[(1-cyclopropyl-1,4-dihydro-3-{[(2-hydroxyethyl)amino]carbonyl}-7-chloro-4-oxo-6-quinolyl)amino]ethyl}amino)propanoyl]-9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A
• 英文别名: [(2S,3S,4R,6R)-6-[[(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-1-oxa-6-azacyclopentadec-13-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl] 3-[2-[[7-chloro-1-cyclopropyl-3-(2-hydroxyethylcarbamoyl)-4-oxoquinolin-6-yl]amino]ethylamino]propanoate
• CAS: 1350922-93-8
• 化学式: C₅₈H₉₅ClN₆O₁₆
• 分子量: 1167.88
• InChiKey: RDZFESNCYMKANI-JSGMXAAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  81
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  280
• 氢给体数：
  8
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  4''-O-[3-({2-[(1-cyclopropyl-1,4-dihydro-3-{[(2-hydroxyethyl)amino]carbonyl}-7-chloro-4-oxo-6-quinolyl)amino]ethyl}amino)propanoyl]-9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 20.0h， 以37%的产率得到4''-O-[3-({2-[(1-cyclopropyl-1,4-dihydro-3-{[(2-hydroxyethyl)amino]carbonyl}-4-oxo-6-quinolyl)amino]ethyl}amino)propanoyl]-9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Synthesis and activity of new macrolones: Conjugates between 6(7)-(2′-aminoethyl)-amino-1-cyclopropyl-3-carboxylic acid (2′-hydroxyethyl) amides and 4″-propenoyl-azithromycin

  摘要：

  A set of novel macrolones containing the flexible C8 basic linker and quinolone 3-(2 '-hydroxyethyl)carboxamido group has been prepared and structurally characterized by NMR and IR spectroscopy, mass spectrometry and molecular modeling. The new compounds were evaluated in vitro against a panel of erythromycin-susceptible and erythromycin-resistant Gram-positive and Gram-negative bacterial strains. Compared to azithromycin, most of the compounds exhibited improved in vitro potency against the key respiratory pathogens. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.011
• 作为产物：
  描述：

  1,1-dimethylethyl {2-[(7-chloro-1-cyclopropyl-3-{[(2-hydroxyethyl)amino]carbonyl}-4-oxo-1,4-dihydro-6-quinolinyl)amino]ethyl}carbamate 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成 4''-O-[3-({2-[(1-cyclopropyl-1,4-dihydro-3-{[(2-hydroxyethyl)amino]carbonyl}-7-chloro-4-oxo-6-quinolyl)amino]ethyl}amino)propanoyl]-9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Synthesis and activity of new macrolones: Conjugates between 6(7)-(2′-aminoethyl)-amino-1-cyclopropyl-3-carboxylic acid (2′-hydroxyethyl) amides and 4″-propenoyl-azithromycin

  摘要：

  A set of novel macrolones containing the flexible C8 basic linker and quinolone 3-(2 '-hydroxyethyl)carboxamido group has been prepared and structurally characterized by NMR and IR spectroscopy, mass spectrometry and molecular modeling. The new compounds were evaluated in vitro against a panel of erythromycin-susceptible and erythromycin-resistant Gram-positive and Gram-negative bacterial strains. Compared to azithromycin, most of the compounds exhibited improved in vitro potency against the key respiratory pathogens. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.011

文献信息

• Synthesis and activity of new macrolones: Conjugates between 6(7)-(2′-aminoethyl)-amino-1-cyclopropyl-3-carboxylic acid (2′-hydroxyethyl) amides and 4″-propenoyl-azithromycin
  作者：Samra Kapić、Andrea Fajdetić、Sanja Koštrun、Ana Čikoš、Hana Čipčić Paljetak、Roberto Antolović、David J. Holmes、Sulejman Alihodžić

  DOI：10.1016/j.bmc.2011.07.011

  日期：2011.12

  A set of novel macrolones containing the flexible C8 basic linker and quinolone 3-(2 '-hydroxyethyl)carboxamido group has been prepared and structurally characterized by NMR and IR spectroscopy, mass spectrometry and molecular modeling. The new compounds were evaluated in vitro against a panel of erythromycin-susceptible and erythromycin-resistant Gram-positive and Gram-negative bacterial strains. Compared to azithromycin, most of the compounds exhibited improved in vitro potency against the key respiratory pathogens. (C) 2011 Elsevier Ltd. All rights reserved.