erythromycin A 9-oxime 9,2',4''-triacetate | 625389-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: erythromycin A 9-oxime 9,2',4''-triacetate
• 英文别名: erythromycin A 9-oxime 9,2',4"-triacetate；erythromycina 9-oxime 9,2',4"-triacetate；erythromycin oxime 2',4",9-triacetate；erythromycin A oxime 2',4'',9-triacetate；ery-9-oxime triacetate；[(2S,3R,4S,6R)-2-[[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-acetyloxyimino-4-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-2-oxo-oxacyclotetradec-6-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate
• CAS: 625389-96-0
• 化学式: C₄₃H₇₄N₂O₁₆
• 分子量: 875.064
• InChiKey: BKGWUHRDLVGDBI-HZLGROLTSA-N

物化性质

• 沸点：
  852.3±75.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  61
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  228
• 氢给体数：
  3
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  erythromycin A 9-oxime 9,2',4''-triacetate 在 乙酸铵 、 盐酸 、 titanium(III) chloride 、 tris(dibenzylideneacetone)dipalladium (0) 、 戴斯-马丁氧化剂 、 三乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 EP-001304
  参考文献：
  名称：

  Synthesis of Novel 6,11-O-Bridged Bicyclic Ketolides via a Palladium-Catalyzed Bis-allylation

  摘要：

  A bridging chemistry process was developed to form an ether bridge between 6-O and 11-O of erythromycin A via a tandem or stepwise palladium-catalyzed bis-pi-allylation. By applying this bridging process, new 6,11-O-bridged bicyclic ketolides (BBKs) were synthesized. These BBKs showed good antibacterial activities against the macrolide-susceptible strains as well as mef-resistant strains and served as a good core for further modifications to study the structure-activity relationship (SAR) and to overcome bacterial resistance.

  DOI：

  10.1021/ol048336r
• 作为产物：
  描述：

  乙酸酐 、 erythromycin A 9-(E)-oxime 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以80%的产率得到erythromycin A 9-oxime 9,2',4''-triacetate
  参考文献：
  名称：

  有效的大规模合成EDP-420，一流的桥接双环大环内酯（BBM）抗生素候选药物

  摘要：

  描述了新型桥联双环大环内酯候选药物EDP-420（1）的多步骤，实用且经济高效的合成方法。从廉价且可商购的红霉素A 9-肟开始，当前的化学过程涉及一系列转化：三乙酰化，Pd催化的O，O-双-烯丙基化（桥形成），酸催化的糖裂解，肟还原，乙酰化， Os催化桥烯烃氧化裂解，Corey-Kim氧化，桥肟形成，脱保护和最终纯化。多千克量已合成。

  DOI：

  10.1021/op900228u

文献信息

• [EN] 6-11 BICYCLIC KETOLIDE DERIVATIVES<br/>[FR] DERIVES KETOLIDES BICYCLIQUES 6-11
  申请人：ENANTA PHARM INC

  公开号：WO2005061525A1

  公开（公告）日：2005-07-07

  The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: (I) which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.

  本发明公开了具有以下结构的化合物，或其药学上可接受的盐、酯或前药：(I)，这些化合物具有抗菌性能。本发明还涉及包含上述化合物的药物组合物，用于给需要抗生素治疗的受试者进行治疗。该发明还涉及通过给予包含本发明化合物的药物组合物来治疗受试者的细菌感染的方法。该发明还包括制备本发明化合物的方法。
• [EN] 6-11 BICYCLIC KETOLIDE DRIVATIVES<br/>[FR] DERIVES DE KETOLIDE 6-11 BICYCLIQUES
  申请人：ENANTA PHARM INC

  公开号：WO2005061526A1

  公开（公告）日：2005-07-07

  The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: Formule (I) which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.

  本发明公开了具有以下结构的化合物I，或其药学上可接受的盐、酯或前药：Formule (I)，其具有抗菌性能。本发明还涉及包括上述化合物的药物组合物，用于给需要抗生素治疗的受试者使用。该发明还涉及通过给予包含本发明化合物的药物组合物来治疗受试者的细菌感染的方法。该发明还包括制备本发明化合物的方法。
• [EN] 6, 11-4-CARBON BRIDGED ERYTHROMYCIN DERIVATIVES<br/>[FR] DERIVES D'ERYTHROMYCINE A PONTS CARBONE 6,11-4
  申请人：ENANTA PHARM INC

  公开号：WO2004011009A1

  公开（公告）日：2004-02-05

  Novel 6,11-4-carbon bridged erythromycin derivatives and pharmaceutically-acceptable compositions comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically-acceptable carrier are described. Also described are methods for treating bacterial infections by administering to an animal a pharmaceutical composition containing a therapeutically effective amount of a compound of the invention and processes for the preparation of such compounds.

  描述了一种6,11-4-碳桥联的红霉素衍生物和药学上可接受的组合物，其中包含本发明化合物的治疗有效量，并与药学上可接受的载体结合。还描述了通过向动物投与含有本发明化合物治疗有效量的药物组合物来治疗细菌感染的方法，以及制备这种化合物的方法。
• Processes for the preparation of 0-(2-aminobenzo[d]oxazol-5-yl)methyl hydroxylamine for the synthesis of 6,11-bicyclic erythromycin derivative EDP-182
  申请人：Xu Guoyou

  公开号：US20070207972A1

  公开（公告）日：2007-09-06

  The present invention relates to processes and intermediates for the preparation of 6-11 bicyclic erythromycin derivative known as EDP-182 (IX-a). In particular, the present invention relates to processes and intermediates for the preparation of O-(2-aminobenzo[d]oxazol-5-yl)methyl hydroxylamine:

  本发明涉及用于制备被称为EDP-182（IX-a）的6-11环式红霉素衍生物的过程和中间体。具体而言，本发明涉及用于制备O-(2-氨基苯并[d]噁唑-5-基)甲基羟胺的过程和中间体。
• [EN] BRIDGED MACROCYCLIC COMPOUNDS AND PROCESSES FOR THE PREPARATION THEREOF<br/>[FR] COMPOSES MACROCYCLIQUES PONTES ET PROCEDES DE PREPARATION DESDITS COMPOSES
  申请人：ENANTA PHARM INC

  公开号：WO2005080408A1

  公开（公告）日：2005-09-01

  The present invention provides a method for preparing bridged macrocyclic compounds comprising the step of reacting a macrocyclic compound characterized by having at least two nucleophilic moieties with a bifunctional bridging reagent optionally in the presence of a catalyst, thereby producing a bridged macrocyclic product.

  本发明提供了一种制备桥联大环化合物的方法，包括以下步骤：将至少具有两个亲核基团的大环化合物与双功能桥接试剂反应，可选地在催化剂的存在下进行，从而产生桥联大环产物。