3-decladinose-6,11-O,O-bridged erythromycin A 9-imine | 808765-29-9

• 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
• 英文别名: [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(1R,2R,3R,6R,7S,8S,9R,10R,16S,18R)-3-ethyl-2,7-dihydroxy-17-imino-2,6,8,10,16,18-hexamethyl-13-methylidene-5-oxo-4,11,15-trioxabicyclo[8.5.4]nonadecan-9-yl]oxy]-6-methyloxan-3-yl] acetate
• CAS: 808765-29-9
• 化学式: C₃₅H₆₀N₂O₁₀
• 分子量: 668.869
• InChiKey: ZCQJFKIZZIMUQB-CJLLHTFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  47
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-decladinose-6,11-O,O-bridged erythromycin A 9-imine 在 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 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 盐酸 、 4-二甲氨基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 titanium(III) chloride 、 三乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 生成 3-decladinose-6,11-O,O-bridged erythromycin A 9-imine
  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

• 6, 11-bridged tricyclic macrolides
  申请人：Or Sun Yat

  公开号：US20070082853A1

  公开（公告）日：2007-04-12

  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.

  本发明公开了具有以下结构的化合物I，或其药学上可接受的盐、酯或前药：这些化合物具有抗菌性能。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受试者施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。
• 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。
• PROCESSES FOR THE PREPARATION OF 2 FLUORO 6-11 BICYCLIC ERYTHROMYCIN DERIVATIVES
  申请人：Xu Guoyou

  公开号：US20090281293A1

  公开（公告）日：2009-11-12

  The present invention relates to processes and intermediates for the preparation of 2-fluoro 6-11 bicyclic erythromycin derivatives. In particular, the present invention relates to processes and intermediates for the preparation of a compound of formula (X-c):

  本发明涉及用于制备2-氟-6-11环状红霉素衍生物的过程和中间体。特别地，本发明涉及用于制备式（X-c）化合物的过程和中间体。
• PROCESSES FOR THE PREPARATION OF 2-FLUORO 6-11 BICYCLIC ERYTHROMYCIN DERIVATIVES
  申请人：Enanta Pharmaceuticals, Inc.

  公开号：US20140073797A1

  公开（公告）日：2014-03-13

  The present invention relates to processes and intermediates for the preparation of 2-fluoro 6-11 bicyclic erythromycin derivatives. In particular, the present invention relates to processes and intermediates for the preparation of a compound of formula (X-c):

  本发明涉及用于制备2-氟-6-11环状红霉素衍生物的过程和中间体。特别地，本发明涉及用于制备化合物（X-c）的过程和中间体。