(9S)-3-descladinosil-3'-desmethyl-3'-acetyl-9-deoxo-9-dehydro-erythromycin A | 654076-73-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (9S)-3-descladinosil-3'-desmethyl-3'-acetyl-9-deoxo-9-dehydro-erythromycin A
• 英文别名: 5P8VR47M4P；N-[(2S,3R,4S,6R)-2-[[(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-4,7,10,12,13-pentahydroxy-3,5,7,9,11,13-hexamethyl-2-oxo-oxacyclotetradec-6-yl]oxy]-3-hydroxy-6-methyloxan-4-yl]-N-methylacetamide
• CAS: 654076-73-0
• 化学式: C₃₀H₅₅NO₁₁
• 分子量: 605.767
• InChiKey: YYAIHIDSVFXXHN-CIHMTEDYSA-N

物化性质

• 沸点：
  773.2±60.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  186
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  红霉素 在 盐酸 、 sodium tetrahydroborate 、 三乙胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (9S)-3-descladinosil-3'-desmethyl-3'-acetyl-9-deoxo-9-dehydro-erythromycin A
  参考文献：
  名称：

  Design, synthesis and in vivo activity of 9-(S)-dihydroerythromycin derivatives as potent anti-inflammatory agents

  摘要：

  The synthesis of a new class of 9-(S)-dihydroerythromycin derivatives and their anti-inflammatory activity on in vivo PMA assay are described. Modifying the desosamine sugar on the C-3' amino group, it was possible to differentiate between anti-biotic and anti-flammatory action. The compounds are completely devoid of anti-microbial effects but their anti-inflammatory properties are enhanced. These results strongly suggest the potential of macrolides as a new class of anti-inflammatory agents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.076

文献信息

• [EN] MACROLIDE COMPOUNDS ENDOWED WITH ANTIINFLAMMATORY ACTIVITY<br/>[FR] COMPOSES DE MACROLIDES AYANT UNE ACTIVITE ANTI-INFLAMMATOIRE
  申请人：ZAMBON SPA

  公开号：WO2004013153A3

  公开（公告）日：2004-04-08
• Design, synthesis and in vivo activity of 9-(S)-dihydroerythromycin derivatives as potent anti-inflammatory agents
  作者：A. Mereu、E. Moriggi、M. Napoletano、C. Regazzoni、S. Manfredini、T.P. Mercurio、F. Pellacini

  DOI：10.1016/j.bmcl.2006.08.076

  日期：2006.11

  The synthesis of a new class of 9-(S)-dihydroerythromycin derivatives and their anti-inflammatory activity on in vivo PMA assay are described. Modifying the desosamine sugar on the C-3' amino group, it was possible to differentiate between anti-biotic and anti-flammatory action. The compounds are completely devoid of anti-microbial effects but their anti-inflammatory properties are enhanced. These results strongly suggest the potential of macrolides as a new class of anti-inflammatory agents. (c) 2006 Elsevier Ltd. All rights reserved.