acetic acid 2-[4-(5-acetoxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-14-ethyl-12,13-dihydroxy-7-(2-hydroxymethyl-allyloxy)-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yloxy]-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester | 625390-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetic acid 2-[4-(5-acetoxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-14-ethyl-12,13-dihydroxy-7-(2-hydroxymethyl-allyloxy)-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yloxy]-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester
• CAS: 625390-16-1
• 化学式: C₄₅H₇₇NO₁₆
• 分子量: 888.103
• InChiKey: JQPUNSRVDBRKMA-GZSDJEQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  62.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  215.28
• 氢给体数：
  3.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  acetic acid 2-[4-(5-acetoxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-14-ethyl-12,13-dihydroxy-7-(2-hydroxymethyl-allyloxy)-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yloxy]-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester 在 盐酸 、 4-二甲氨基吡啶 、 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 16.0h， 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 甲酸 、 sodium hydrogensulfite 作用下， 以 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 9.0h， 生成 acetic acid 2-[4-(5-acetoxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-14-ethyl-12,13-dihydroxy-7-(2-hydroxymethyl-allyloxy)-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yloxy]-4-dimethylamino-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 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。