泰利霉素中间体 (7A) | 160145-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 泰利霉素中间体 (7A)
• 中文别名: 泰利霉素中间体(7A)；泰利中间体(7A)
• 英文名称: (2R,3S,7R,9R,10R,11R,13R,E)-10-(((2S,3R,4S,6R)-3-acetoxy-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-9-methoxy-3,5,7,9,11,13-hexamethyl-6,12,14-trioxooxacyclotetradec-4-en-3-yl 1H-imidazole-1-carboxylate
• 英文别名: 2'-O-acetyl-10,11-didehydro-11-deoxy-12-O-(1H-1-imidazoylcarbonyl)-3-O-descladinosyl-3-oxo-6-O-methyl-erythromycin A；Erythromycin, 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-I+/--L-ribo-hexopyranosyl)oxy]-10,11-didehydro-11-deoxy-6-O-methyl-3-oxo-, 2a(2)-acetate 12-(1H-imidazole-1-carboxylate)；[(2R,3S,4E,7R,9R,10R,11R,13R)-10-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-1-oxacyclotetradec-4-en-3-yl] imidazole-1-carboxylate
• CAS: 160145-83-5
• 化学式: C₃₆H₅₅N₃O₁₁
• 分子量: 705.846
• InChiKey: KXBIFULZQOIGPO-DVYKOBGPSA-N

物化性质

• 沸点：
  784.6±70.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  50
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  泰利霉素中间体 (7A) 在 氨 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Ketolides (6-O-Methyl-3-oxoerythromycin Derivatives):  A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens

  摘要：

  In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called "ketolides". A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.

  DOI：

  10.1021/jm980240d
• 作为产物：
  描述：

  克拉霉素 在 盐酸 、 N-氯代丁二酰亚胺 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 60.08h， 生成 泰利霉素中间体 (7A)
  参考文献：
  名称：

  一种修改 14 元内酯大环内酯类抗生素支架的方法

  摘要：

  通过一种新型乙烯酮缩醛在酸性条件下获得了具有 (12 R ) 构型的酮内酯衍生物。大环体系中这种非典型的 β-酮烯酮缩醛中间体的结构已通过 NMR 和 X 射线方法确定。在高温下使用碱性条件产生了新的双 α,β-不饱和酮大环内酯衍生物，具有 (4 E )-构型作为折叠或折叠构象的两种构象异构体。

  DOI：

  10.1021/acs.joc.1c02799

文献信息

• Synthesis of novel macrolide derivatives with imidazo[4,5-b]pyridinyl sulfur contained alkyl side chains and their antibacterial activity
  作者：Peng Xu、Lu Liu、Xiao-zhuo Chen、Yun Li、Jian Liu、Zhi-ping Jin、Guang-qiang Wang、Ping-sheng Lei

  DOI：10.1016/j.bmcl.2009.06.023

  日期：2009.8

  In an effort to find new antibiotics, a novel series of 14-membered macrolides with imidazo[4,5-b]pyridinyl sulfur contained alkyl side chains has been synthesized based on commercially available clarithromycin. Chemical transformation of hydroxy group at position C-3 afforded range of ketolides and acylides. Compared to telithromycin, compound 15a demonstrated improved in vitro activity against e

  为了寻找新的抗生素，已经基于市售的克拉霉素合成了一系列新的具有咪唑并[4，5- b ]吡啶基硫烷基侧链的14元大环内酯类化合物。在C-3位上的羟基的化学转化提供了酮醇化物和酰化物的范围。与替利霉素相比，化合物15a表现出对红霉素敏感和耐药菌株的体外活性提高。
• [EN] PROCESS FOR THE PRODUCTION OF TELITHROMYCIN<br/>[FR] PROCÉDÉ DE FABRICATION DE TÉLITHROMYCINE
  申请人：SANDOZ AG

  公开号：WO2009053259A1

  公开（公告）日：2009-04-30

  The present invention relates to a process for the preparation of erythromysin derivatives, in particular telithromycin of formula (I) and its pharmaceutically acceptable salts, providing the isolated intermediates in crystalline form of superior stability and purity.

  本发明涉及一种制备红霉素衍生物的方法，特别是制备式(I)的特利霉素及其药学上可接受的盐，提供具有卓越稳定性和纯度的晶体中间体。
• Novel process for the preparation of telithromycin
  申请人：Deshpande Pandurang Balwant

  公开号：US20080051352A1

  公开（公告）日：2008-02-28

  The present invention relates to the process for the preparation of compounds of formula (I) or its pharmaceutically acceptable salts wherein, R is

  本发明涉及制备式(I)化合物或其药学上可接受的盐的过程，其中R为
• Erythromycin compounds
  申请人：Roussel Uclaf

  公开号：US05635485A1

  公开（公告）日：1997-06-03

  An erythromycin compound of Formula I or its non-toxic acid addition salt having antibiotic activity.

  具有抗生素活性的式I的红霉素化合物或其非毒性酸加成盐。
• Eryhromycin derivatives
  申请人：Roussel Uclaf

  公开号：US05614614A1

  公开（公告）日：1997-03-25

  Novel intermediates for the preparation of the compounds of Formula I wherein the substituents are as defined in the specification.

  为制备式I化合物中定义的取代基的新型中间体。