4''-O-[3-({2-[(3-carboxy-7-chloro-1-cyclopropyl-1,4-dihydro-4-oxoquinolin-6-yl)amino]ethyl}amino)propanoyl]-6-O-methyl-8a-aza-8a-homoerythromycin A | 528849-89-0

• 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-[(3-carboxy-7-chloro-1-cyclopropyl-1,4-dihydro-4-oxoquinolin-6-yl)amino]ethyl}amino)propanoyl]-6-O-methyl-8a-aza-8a-homoerythromycin A
• CAS: 528849-89-0
• 化学式: C₅₆H₈₈ClN₅O₁₇
• 分子量: 1138.79
• InChiKey: HAJISKUPMXJGDF-ADWFHHRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  79.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  284.37
• 氢给体数：
  7.0
• 氢受体数：
  20.0

反应信息

• 作为产物：
  描述：

  6-[(2-氨基乙基)氨基]-7-氯-1-环丙基-1,4-二氢-4-氧代-喹啉-3-羧酸 、 4"-O-propenoyl-6-O-methyl-8a-aza-8a-homoerythromycin A 以 异丙醇 为溶剂， 反应 72.0h， 以0.053 g的产率得到4''-O-[3-({2-[(3-carboxy-7-chloro-1-cyclopropyl-1,4-dihydro-4-oxoquinolin-6-yl)amino]ethyl}amino)propanoyl]-6-O-methyl-8a-aza-8a-homoerythromycin A
  参考文献：
  名称：

  4″-O-(ω-Quinolylamino-alkylamino)propionyl derivatives of selected macrolides with the activity against the key erythromycin resistant respiratory pathogens

  摘要：

  Four macrolides-6-O-methyl-8a-aza-8a-homoerythromycin, clarithromycin, azithromycin and azithromycin 11,12-cyclic carbonate, have been selected for the construction of a series of new quinolone derivatives. The quinolone moiety is connected to the macrolide scaffold via a diaminoaklyl 4"-O-propionyl ester chain of varying length. At the terminus the linker is attached via one of the nitrogen atoms in the linker at C(6) or C(7) of the quinolone. Many of compounds described, particularly clarithromycin derivative 37, and azithromycin derivatives 48 and 55, exhibited excellent antibacterial activity against a wide range of clinically relevant macrolide-resistant organisms, with profiles superior to that of telithromycin, an enhanced spectrum ketolide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.049