11-deoxy-10,11-didehydro-3-de[(2,6-dideoxy-3C-methyl-3O-methyl-α-L-ribohexopyranosyl)oxy]-6O-methyl-3-oxoerythromycin | 153954-86-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11-deoxy-10,11-didehydro-3-de[(2,6-dideoxy-3C-methyl-3O-methyl-α-L-ribohexopyranosyl)oxy]-6O-methyl-3-oxoerythromycin
• 英文别名: (3R,5R,6R,7R,9R,11E,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradec-11-ene-2,4,10-trione
• CAS: 153954-86-0
• 化学式: C₃₀H₅₁NO₉
• 分子量: 569.736
• InChiKey: CESZSCMZQIWLQY-KMBQMOQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  11-deoxy-10,11-didehydro-3-de[(2,6-dideoxy-3C-methyl-3O-methyl-α-L-ribohexopyranosyl)oxy]-6O-methyl-3-oxoerythromycin 在 咪唑 、 N-fluorosulfonimide 、 potassium tert-butylate 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 11-deoxy-10,11-didehydro-3-de[(2,6-dideoxy-3C-methyl-3O-methyl-α-L-ribohexopyranosyl)oxy]-6O-methyl-3-oxoerythromycin-2α-fluoro
  参考文献：
  名称：

  β-Keto-ester chemistry and ketolides. synthesis and antibacterial activity of 2-halogeno, 2-methyl and 2,3 enol-ether ketolides

  摘要：

  The effect of 2,3 modifications on the antibacterial activity of ketolides was evaluated by introducing substituents in position 2 and converting the C-1, C-2, C-3 beta-keto-ester into stable 2,3 enol-ether or 2,3 anhydro derivatives. Introduction of a fluorine in C-2. is beneficial with regard to the overall antibacterial spectrum whereas the enol-ether and 2,3 unsaturated compounds, as well as the bulky gem dimethyl or 2-chloro derivatives, are less active particularly against erythromycin resistant strains. A 2-fluoro ketolide derivative demonstrates good antibacterial activity and in vivo efficacy against multi-resistant Streptococcus pneumoniae. Compared to azithromycin against Haemophilus influenzae, this compound is equivalent in vitro and slightly more active in vivo. These results demonstrate that within the ketolide class, to retain good antibacterial activity, position needs to remain tetrahedral and tolerates only very small substituents such as fluorine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00392-9
• 作为产物：
  描述：

  (2S,3R,4S,6R)-4-(dimethylamino)-2-(((3R,5R,6R,7R,9R,13S,14R,E)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4,10-trioxooxacyclotetradec-11-en-6-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate 在 甲醇 作用下， 反应 44.0h， 生成 11-deoxy-10,11-didehydro-3-de[(2,6-dideoxy-3C-methyl-3O-methyl-α-L-ribohexopyranosyl)oxy]-6O-methyl-3-oxoerythromycin
  参考文献：
  名称：

  2-halogenated derivatives of 5-0 desosaminyl-erythronolide A, their preparation process and their antibiotic use

  摘要：

  该式中的新化合物具有抗生素性质，其中取代基的定义如申请中所述。

  公开号：

  US06352983B1

文献信息

• Ketolide Derivatives as Antibacterial Agents
  申请人：Das Biswajit

  公开号：US20080287376A1

  公开（公告）日：2008-11-20

  The present invention provides ketolide derivatives, which can be used as antibacterial agents. In particular, compounds described herein can be used for treating or preventing conditions caused by or contributed to by Gram-positive, Gram-negative or anaerobic bacteria, more particularly against, for example, Staphylococci, Streptococci, Enterococci, Haemophilus, Moraxalla spp. Chlamydia spp., Mycoplasm, Legionella spp., Mycobacterium, Helicobacter, Clostridium, Bacteroides, Corynebaclerium, Bacillus or Enterobactericeae. Also provided are processes for preparing such ketolide derivatives, pharmaceutical compositions thereof, and methods of treating bacterial infections.

  本发明提供了酮烯类衍生物，可用作抗菌剂。具体而言，本文所描述的化合物可用于治疗或预防由革兰氏阳性菌、革兰氏阴性菌或厌氧菌引起或促成的疾病，更具体地针对例如葡萄球菌、链球菌、肠球菌、衣原体、流感嗜血杆菌属、沙眼衣原体属、支原体、军团菌属、分枝杆菌、幽门螺杆菌、梭状芽孢杆菌、拟杆菌属、芽孢杆菌或肠杆菌科。还提供了制备此类酮烯类衍生物的方法、其制药组合物以及治疗细菌感染的方法。
• WO2006/80954
  申请人：——

  公开号：——

  公开（公告）日：——
• 2-halogenated derivatives of 5-0 desosaminyl-erythronolide A, their preparation process and their antibiotic use
  申请人：Aventis Pharma S.A.

  公开号：US06352983B1

  公开（公告）日：2002-03-05

  Novel compounds of the formula wherein the substituents are defined as in the application having antibiotic properties.

  该式中的新化合物具有抗生素性质，其中取代基的定义如申请中所述。
• β-Keto-ester chemistry and ketolides. synthesis and antibacterial activity of 2-halogeno, 2-methyl and 2,3 enol-ether ketolides
  作者：Alexis Denis、François Bretin、Claude Fromentin、A Bonnet、Alain Bonnefoy、Constantin Agouridas、G Piltan

  DOI：10.1016/s0960-894x(00)00392-9

  日期：2000.9

  The effect of 2,3 modifications on the antibacterial activity of ketolides was evaluated by introducing substituents in position 2 and converting the C-1, C-2, C-3 beta-keto-ester into stable 2,3 enol-ether or 2,3 anhydro derivatives. Introduction of a fluorine in C-2. is beneficial with regard to the overall antibacterial spectrum whereas the enol-ether and 2,3 unsaturated compounds, as well as the bulky gem dimethyl or 2-chloro derivatives, are less active particularly against erythromycin resistant strains. A 2-fluoro ketolide derivative demonstrates good antibacterial activity and in vivo efficacy against multi-resistant Streptococcus pneumoniae. Compared to azithromycin against Haemophilus influenzae, this compound is equivalent in vitro and slightly more active in vivo. These results demonstrate that within the ketolide class, to retain good antibacterial activity, position needs to remain tetrahedral and tolerates only very small substituents such as fluorine. (C) 2000 Elsevier Science Ltd. All rights reserved.