11-O-Me-2'-O-acetyl-azithromycin | 797793-78-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11-O-Me-2'-O-acetyl-azithromycin
• 英文别名: 2'-O-Ac-11-O-methyl-azithromycin；2'-O-Acetyl-11-O-methyl-azithromycin；[(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(2R,3R,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,10-dihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-4-methoxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-1-oxa-6-azacyclopentadec-11-yl]oxy]-6-methyloxan-3-yl] acetate
• CAS: 797793-78-3
• 化学式: C₄₁H₇₆N₂O₁₃
• 分子量: 805.06
• InChiKey: XDOKQVOPJIALOW-BHPMJYKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  56
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  175
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  11-O-Me-2'-O-acetyl-azithromycin 在 platinum(IV) oxide 甲醇 、 氢气 、 sodium hydride 、 叔丁醇 作用下， 以 溶剂黄146 为溶剂， 50.0 ℃ 、500.01 kPa 条件下， 反应 37.0h， 生成 4"-O-(3-aminopropyl)-11-O-methyl-azithromycin
  参考文献：
  名称：

  Macrolides With Anti-Inflammatory Activity

  摘要：

  本发明涉及具有抗炎活性的新型半合成大环内酯类化合物。更具体地说，该发明涉及在4″位置取代的14-和15-环大环内酯类化合物，及其药学上可接受的衍生物，用于其制备的工艺和中间体，含有它们的制剂，以及它们在治疗人类和动物的炎症性疾病和症状中的活性和用途，特别是那些与过度分泌TNF-α、IL-1、IL-8、IL-2或IL-5有关的疾病；和/或抑制过度淋巴细胞增殖；和/或过度粒细胞脱颗粒的抑制剂。

  公开号：

  US20080221046A1
• 作为产物：
  描述：

  11-O-methyl-azithromycin 、 乙酸酐 以 乙酸乙酯 为溶剂， 反应 12.0h， 生成 11-O-Me-2'-O-acetyl-azithromycin
  参考文献：
  名称：

  [EN] MACROLIDES SUBSTITUDED AT THE 4"-POSITION
  [FR] MACROLIDES SUBSTITUES EN POSITION 4''

  摘要：

  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。

  公开号：

  WO2004101585A1

文献信息

• [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。
• Synthesis of macrolones with central piperazine ring in the linker and its influence on antibacterial activity
  作者：Samra Kapić、Hana Čipčić Paljetak、Ivana Palej Jakopović、Andrea Fajdetić、Marina Ilijaš、Vlado Štimac、Karmen Brajša、David J. Holmes、John Berge、Sulejman Alihodžić

  DOI：10.1016/j.bmc.2011.07.010

  日期：2011.12

  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.
• WO2006/106440
  申请人：——

  公开号：——

  公开（公告）日：——
• 6-Alkylquinolone-3-carboxylic acid tethered to macrolides synthesis and antimicrobial profile
  作者：Samra Kapić、Hana Čipčić Paljetak、Sulejman Alihodžić、Roberto Antolović、Vesna Eraković Haber、Richard L. Jarvest、David J. Holmes、John P. Broskey、Eric Hunt

  DOI：10.1016/j.bmc.2010.06.048

  日期：2010.9

  Two series of clarithromycin and azithromycin derivatives with terminal 6-alkylquinolone-3-carboxylic unit with central ether bond in the linker were prepared and tested for antimicrobial activity. Quinolonelinker intermediates were prepared by Sonogashira-type C(6)-alkynylation of 6-iodo-quinolone precursors. In the last step, 400 site-selective acylation of 2'-protected macrolides was completed with the EDC reagent, which selectively activated a terminal, aliphatic carboxylic group in dicarboxylic intermediates. Antimicrobial activity of the new series of macrolones is discussed. The most potent compound, 4"-O-6-[3-(3-carboxy-1-ethyl-4-oxo-1,4-dihydroquinolin-6-yl)-propoxy]-hexanoyl}-azithromycin (10), is highly active against bacterial respiratory pathogens resistant to macrolide antibiotics and represents a promising lead for further investigation. (C) 2010 Elsevier Ltd. All rights reserved.
• US7547679B2
  申请人：——

  公开号：US7547679B2

  公开（公告）日：2009-06-16