(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[methyl-[3-(1,3-thiazol-2-ylmethylamino)propyl]amino]oxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one | 654076-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[methyl-[3-(1,3-thiazol-2-ylmethylamino)propyl]amino]oxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
• CAS: 654076-82-1
• 化学式: C₄₃H₇₇N₃O₁₃S
• 分子量: 876.163
• InChiKey: CXYNIEXAKLZPPH-KYTGTITISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  60
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  250
• 氢给体数：
  7
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[methyl-[3-(1,3-thiazol-2-ylmethylamino)propyl]amino]oxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one 在 盐酸 作用下， 以 甲醇 为溶剂， 生成
  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
• 作为产物：
  描述：

  红霉素 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 23.0h， 生成 (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[methyl-[3-(1,3-thiazol-2-ylmethylamino)propyl]amino]oxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
  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.