7-chloro-1-cyclopropyl-6-[2-[[3-[(2S,3S,4R,6R)-6-[[(1R,2R,5R,6S,7S,8R,9R,11R,14R,15R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-hydroxy-1,5,7,9,11,13,14-heptamethyl-4,17-dioxo-3,16,18-trioxa-13-azabicyclo[13.3.0]octadecan-6-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl]oxy-3-oxopropyl]amino]ethylamino]-4-oxoquinoline-3-carboxylic acid | 528850-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-chloro-1-cyclopropyl-6-[2-[[3-[(2S,3S,4R,6R)-6-[[(1R,2R,5R,6S,7S,8R,9R,11R,14R,15R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-hydroxy-1,5,7,9,11,13,14-heptamethyl-4,17-dioxo-3,16,18-trioxa-13-azabicyclo[13.3.0]octadecan-6-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl]oxy-3-oxopropyl]amino]ethylamino]-4-oxoquinoline-3-carboxylic acid
• CAS: 528850-15-9
• 化学式: C₅₇H₈₈ClN₅O₁₇
• 分子量: 1150.8
• InChiKey: SZHNJFLSYKVFTM-YWBFNEHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  80
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  263
• 氢给体数：
  5
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  7-chloro-1-cyclopropyl-6-[2-[[3-[(2S,3S,4R,6R)-6-[[(1R,2R,5R,6S,7S,8R,9R,11R,14R,15R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-hydroxy-1,5,7,9,11,13,14-heptamethyl-4,17-dioxo-3,16,18-trioxa-13-azabicyclo[13.3.0]octadecan-6-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl]oxy-3-oxopropyl]amino]ethylamino]-4-oxoquinoline-3-carboxylic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 20.0 ℃ 、200.0 kPa 条件下， 反应 16.0h， 生成 1-cyclopropyl-6-[2-[[3-[(2S,3S,4R,6R)-6-[[(1R,2R,5R,6S,7S,8R,9R,11R,14R,15R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-hydroxy-1,5,7,9,11,13,14-heptamethyl-4,17-dioxo-3,16,18-trioxa-13-azabicyclo[13.3.0]octadecan-6-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl]oxy-3-oxopropyl]amino]ethylamino]-4-oxoquinoline-3-carboxylic acid
  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
• 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 、 11,12-carbonate-11,12-dideoxy-4"-O-propenoylazithromycin 以 异丙醇 为溶剂， 生成 7-chloro-1-cyclopropyl-6-[2-[[3-[(2S,3S,4R,6R)-6-[[(1R,2R,5R,6S,7S,8R,9R,11R,14R,15R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-hydroxy-1,5,7,9,11,13,14-heptamethyl-4,17-dioxo-3,16,18-trioxa-13-azabicyclo[13.3.0]octadecan-6-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl]oxy-3-oxopropyl]amino]ethylamino]-4-oxoquinoline-3-carboxylic acid
  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

文献信息

• 4″-O-(ω-Quinolylamino-alkylamino)propionyl derivatives of selected macrolides with the activity against the key erythromycin resistant respiratory pathogens
  作者：A. Fajdetić、H. Čipčić Paljetak、G. Lazarevski、A. Hutinec、S. Alihodžić、M. Đerek、V. Štimac、D. Andreotti、V. Šunjić、J.M. Berge、S. Mutak、M. Dumić、S. Lociuro、D.J. Holmes、N. Maršić、V. Eraković Haber、R. Spaventi

  DOI：10.1016/j.bmc.2010.06.049

  日期：2010.9

  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.