3-decladinose-6,11-O,O-bridged erythromycin A 9-imine acetamide 2'-acetate | 628703-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-decladinose-6,11-O,O-bridged erythromycin A 9-imine acetamide 2'-acetate
• CAS: 628703-03-7
• 化学式: C₃₇H₆₂N₂O₁₁
• 分子量: 710.906
• InChiKey: QDTKWYNEVOYJRY-WSQFDLHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  50.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  162.65
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-decladinose-6,11-O,O-bridged erythromycin A 9-imine acetamide 2'-acetate 在 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 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：

  erythromycin A 9-(E)-oxime 在 乙酸铵 、 盐酸 、 4-二甲氨基吡啶 、 titanium(III) chloride 、 tris(dibenzylideneacetone)dipalladium (0) 、 三乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 3-decladinose-6,11-O,O-bridged erythromycin A 9-imine acetamide 2'-acetate
  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

文献信息

• 6-11 Bicyclic erythromycin derivatives
  申请人：Vo Huu Nha

  公开号：US20050187169A1

  公开（公告）日：2005-08-25

  The present invention discloses compounds of formulaes I, II, III, or IV, or a racemate, enantiomer, regioisomer, salt, ester or prodrug thereof: 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式I、II、III或IV的化合物，或其拉克米特、对映体、位置异构体、盐、酯或前药： 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，用于治疗需要抗生素治疗的受试者。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 ERYTHROMYCIN DERIVATIVES<br/>[FR] DERIVES DE L'ERYTHROMYCINE 6,11 BICYCLIQUE
  申请人：ENANTA PHARM INC

  公开号：WO2003095466A1

  公开（公告）日：2003-11-20

  The present invention discloses compounds of formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof 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.

  本发明公开了具有抗菌性质的化合物(I)的公式，或其药学上可接受的盐、酯或前药。本发明还涉及包含上述化合物的药物组合物，用于治疗需要抗生素治疗的受试者。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。
• 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] PROCESS FOR THE PREPARATION OF T-11 BICYCLIC ERYTHROMYCIN DERIVATIVES<br/>[FR] PROCEDE DE PREPARATION DE DERIVES BICYCLIQUES 6-11 D'ERYTHROMYCINE
  申请人：ENANTA PHARM INC

  公开号：WO2005070918A1

  公开（公告）日：2005-08-04

  The present invention relates to processes and intermediates for the preparation of 6-11 bicyclic erythromycin derivatives. In particular, the presen tinvention relates to processes and intermediates for the preparation of a compound of formula (IX-c).

  本发明涉及用于制备6-11双环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化合物（IX-c）的过程和中间体。