ethyl 6-[3-(4-{[(1,1-dimethylethyl)oxy]carbonyl}-1-piperazinyl)-1-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-3-quinolinecarboxylate | 869353-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 6-[3-(4-{[(1,1-dimethylethyl)oxy]carbonyl}-1-piperazinyl)-1-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-3-quinolinecarboxylate
• 英文别名: 6-[3-(4-tert-butoxycarbinyl-piperazin-1-yl)-prop-1-ynyl]-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester；6-[3-(4-tert-butoxycarbonyl-piperazin-1-yl)-prop-1-ynyl]-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester；Ethyl 1-ethyl-6-[3-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]prop-1-ynyl]-4-oxoquinoline-3-carboxylate
• CAS: 869353-72-0
• 化学式: C₂₆H₃₃N₃O₅
• 分子量: 467.565
• InChiKey: OERLXFPEJHBAGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 6-[3-(4-{[(1,1-dimethylethyl)oxy]carbonyl}-1-piperazinyl)-1-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-3-quinolinecarboxylate 在 甲醇 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 20.0~80.0 ℃ 、500.01 kPa 条件下， 反应 46.5h， 生成 9-deoxo-4''-O-(3-{4-[3-(1-ethyl-3-ethoxycarbonyl-1,4-dihydro-4-oxo-quinolin-6-yl)propyl]piperazin-1-yl}propionyl)-9a,11-O-dimethyl-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Synthesis of macrolones with central piperazine ring in the linker and its influence on antibacterial activity

  摘要：

  Three macrolides, clarithromycin, azithromycin and 11-O-Me-azithromycin have been selected for the construction of a series of new macrolone derivatives. Quinolone-linker intermediates are prepared by Sonogashira-type C(6)-alkynylation of 6-iodoquinolone precursors. The final macrolones, differing by macrolide moiety and substituents at the position N-1 of the quinolone or by the presence of an ethyl ester or free acid on the quinolone unit attached via a linker.The linker comprises of a central piperazine ring bonded to the 4 ''-O position of cladinose by 3-carbon ester or ether functionality. Modifications of the linker did not improve antibacterial properties compared to the previously reported macrolone compounds. Linker flexibility seems to play an important role for potency against macrolide resistant respiratory pathogens. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.010
• 作为产物：
  描述：

  4-(2-丙炔)哌嗪-1-羧酸叔丁酯 在 copper(l) iodide 、 bis-triphenylphosphine-palladium(II) chloride 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.33h， 生成 ethyl 6-[3-(4-{[(1,1-dimethylethyl)oxy]carbonyl}-1-piperazinyl)-1-propyn-1-yl]-1-ethyl-4-oxo-1,4-dihydro-3-quinolinecarboxylate
  参考文献：
  名称：

  [EN] ESTER LINKED MACROLIDES USEFUL FOR THE TREATMENT OF MICROBIAL INFECTIONS
  [FR] MACROLIDES A LIAISON ESTER UTILES POUR LE TRAITEMENT D'INFECTION MICROBIENNES

  摘要：

  本发明涉及在式（I）的4”位置被取代的14-或15-环大环内酯及其药学上可接受的衍生物，以及它们的制备方法和在人体或动物体内治疗或预防全身或局部微生物感染中的用途。

  公开号：

  WO2005108412A1

文献信息

• [EN] CARBAMATE LINKED MACROLIDES USEFUL FOR THE TREATMENT OF MICROBIAL INFECTIONS<br/>[FR] MACROLIDES A LIAISON CARBAMATE UTILISES DANS LE TRAITEMENT DES INFECTIONS MICROBIENNES
  申请人：PLIVA ISTRAZIVACKI INST D O O

  公开号：WO2005108413A1

  公开（公告）日：2005-11-17

  The present invention relates to 14- or 15-membered macrolides substituted at the 4' position of formula (I) and pharmaceutically acceptable derivatives thereof, to processes for their preparation and their use in therapy or prophylaxis of systemic or topical microbial infections in a human or animal body.

  本发明涉及在式(I)的4'位置被取代的14-或15-元大环内酯及其药学上可接受的衍生物，以及它们的制备过程和在人体或动物体内治疗或预防全身或局部微生物感染中的用途。
• [EN] ESTER LINKED MACROLIDES USEFUL FOR THE TREATMENT OF MICROBIAL INFECTIONS<br/>[FR] MACROLIDES A LIAISON ESTER UTILES POUR LE TRAITEMENT D'INFECTION MICROBIENNES
  申请人：PLIVA ISTRAZIVACKI INST D O O

  公开号：WO2005108412A1

  公开（公告）日：2005-11-17

  The present invention relates to 14- or 15-membered macrolides substituted at the 4” position of formula (I) and pharmaceutically acceptable derivatives thereof, to processes for their preparation and their use in therapy or prophylaxis of systemic or topical microbial infoections in a human or animal body.

  本发明涉及在式（I）的4”位置被取代的14-或15-环大环内酯及其药学上可接受的衍生物，以及它们的制备方法和在人体或动物体内治疗或预防全身或局部微生物感染中的用途。
• Carbamate Linked Macrolides Useful For The Treatment Of Microbial Infections
  申请人：Alihodzic Sulejman

  公开号：US20080249033A1

  公开（公告）日：2008-10-09

  The present invention relates to 14- or 15-membered macrolides substituted at the 4″ position of formula (I) and pharmaceutically acceptable derivatives thereof, to processes for their preparation and their use in therapy or prophylaxis of systemic or topical microbial infections in a human or animal body.

  本发明涉及在公式（I）的4″位置取代的14或15元大环内酯及其药学上可接受的衍生物，以及它们的制备过程和在人或动物体内治疗或预防系统性或局部微生物感染的用途。
• Ester Linked Macrolides Useful For The Treatment of Microbial Infections
  申请人：Alihodzic Sulejman

  公开号：US20080255060A1

  公开（公告）日：2008-10-16

  The present invention relates to 14- or 15-membered macrolides substituted at the 4″ position of formula (I) and pharmaceutically acceptable derivatives thereof, to processes for their preparation and their use in therapy or prophylaxis of systemic or topical microbial infections in a human or animal body.

  本发明涉及在式(I)的4"位置取代的14或15元大环内酯及其药学上可接受的衍生物，以及它们的制备方法和在人或动物体内治疗或预防系统性或局部微生物感染的用途。
• 4'' Amino Linked Macrolides Useful for the Treatment of Microbial Infections
  申请人：Alihodzic Sulejman

  公开号：US20080312167A1

  公开（公告）日：2008-12-18

  The present invention relates to 15-membered macrolides substituted at the 4″ position of formula (I) and pharmaceutically acceptable derivatives thereof, to processes for their preparation and their use in therapy or prophylaxis of systemic or topical microbial infections in a human or animal body.

  本发明涉及式(I)中4″位取代的15元大环内酯及其药学上可接受的衍生物，以及它们的制备方法和在人体或动物体内治疗或预防系统性或局部微生物感染中的应用。