acetic acid 4-dimethylamino-2-(3-ethyl-2,7-dihydroxy-2,6,8,10,16,18-hexamethyl-13-methylene-5,17-dioxo-4,11,15-trioxa-bicyclo[8.5.4]nonadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester | 625390-28-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetic acid 4-dimethylamino-2-(3-ethyl-2,7-dihydroxy-2,6,8,10,16,18-hexamethyl-13-methylene-5,17-dioxo-4,11,15-trioxa-bicyclo[8.5.4]nonadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS: 625390-28-5
• 化学式: C₃₅H₅₉NO₁₁
• 分子量: 669.854
• InChiKey: HDTDKNXTTJLEOP-CJLLHTFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  47.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  150.29
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  acetic acid 4-dimethylamino-2-(3-ethyl-2,7-dihydroxy-2,6,8,10,16,18-hexamethyl-13-methylene-5,17-dioxo-4,11,15-trioxa-bicyclo[8.5.4]nonadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 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 (1R,2R,3R,6R,8R,9R,10R,16R,18R)-9-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-2-hydroxy-2,6,8,10,16,18-hexamethyl-13-methylidene-4,11,15-trioxabicyclo[8.5.4]nonadecane-5,7,17-trione
  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：

  在 盐酸 、 4-二甲氨基吡啶 、 甲酸 、 tris(dibenzylideneacetone)dipalladium (0) 、 sodium hydrogensulfite 、 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 、 水 、 异丙醇 为溶剂， 反应 18.0h， 生成 acetic acid 4-dimethylamino-2-(3-ethyl-2,7-dihydroxy-2,6,8,10,16,18-hexamethyl-13-methylene-5,17-dioxo-4,11,15-trioxa-bicyclo[8.5.4]nonadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
  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

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

  公开号：WO2003097659A1

  公开（公告）日：2003-11-27

  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.

  本发明公开了以下式(I)的化合物，或其药学上可接受的盐、酯或前药：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使用。该发明还涉及通过给受试者使用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 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] METHOD FOR THE PRODUCTION OF MACROLIDES<br/>[FR] PROCEDE DE FABRICATION DE MACROLIDES
  申请人：ALPHARMA APS

  公开号：WO2006087238A1

  公开（公告）日：2006-08-24

  (EN) A process for the conversion of 6-11 bridged bicyclic ketolide or erythromycin oximes to 6-11 bridged bicyclic ketolides or erythromycins comprises reacting a 6-11 bridged macrolide with a deoximating agent, preferably an oxidative deoximating agent such as Dess-Martin periodinane. The procedure may comprise deoximation of certain erythromycin A C-9 oxime derivatives with regeneration of the C-9 keto function.(FR) L'invention porte sur un procédé de conversion d'un cétolide bicyclique ou d'oximes d'érythromycine à pontage 6-11 en cétolides bicycliques ou érythromycines à pontage en 6-11, consistant à faire réagir un macrolide à pontage en 6-11 avec un agent de déoxymation, de préférence un agent de déoxymation oxydant tel que du Dess-Martin periodinane. Ce procédé comprend la déoxymation de certains dérivés d'érythromycine A C-9 oxime accompagnée de la régénération de la fonction C-9 céto.

  一种将6-11桥式双环酮酰胺或红霉素肟转化为6-11桥式双环酮酰胺或红霉素的方法包括将6-11桥式大环内酯与去氧化剂反应，优选为氧化去氧化剂，例如Dess-Martin periodinane。该过程可以包括对某些红霉素A C-9肟衍生物进行去氧化处理，并再生C-9酮功能。