N-[(2S,3R,4S,6R)-2-[[(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-3,5,7,9,11,13-hexamethyl-2-oxo-oxacyclotetradec-6-yl]oxy]-3-hydroxy-6-methyloxan-4-yl]-N-methylacetamide | 654076-78-5

• 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: N-[(2S,3R,4S,6R)-2-[[(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-3,5,7,9,11,13-hexamethyl-2-oxo-oxacyclotetradec-6-yl]oxy]-3-hydroxy-6-methyloxan-4-yl]-N-methylacetamide
• CAS: 654076-78-5
• 化学式: C₃₈H₆₉NO₁₄
• 分子量: 763.964
• InChiKey: FJDPTXHWBGHPOP-CASXJEATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  53
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  214
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4S,6R)-2-[[(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-3,5,7,9,11,13-hexamethyl-2-oxo-oxacyclotetradec-6-yl]oxy]-3-hydroxy-6-methyloxan-4-yl]-N-methylacetamide 在 盐酸 作用下， 以 甲醇 为溶剂， 以90%的产率得到(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
• 作为产物：
  描述：

  红霉素 在 sodium tetrahydroborate 、 三乙胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 N-[(2S,3R,4S,6R)-2-[[(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-3,5,7,9,11,13-hexamethyl-2-oxo-oxacyclotetradec-6-yl]oxy]-3-hydroxy-6-methyloxan-4-yl]-N-methylacetamide
  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
• COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING DISEASES AND DISORDERS ASSOCIATED WITH MUTANT KCNJ5
  申请人：The Rockefeller University

  公开号：US20200147113A1

  公开（公告）日：2020-05-14

  The present invention relates to the discovery that mutant KCNJ5 is associated with adrenal diseases and disorders. The invention includes compositions and methods for the diagnosis and treatment of adrenal diseases and disorders, based upon the presence or absence of a KCNJ5 mutation that is associated with an adrenal disease or disorder.
• 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.