(3R,4S,5R,6S,7S,10S,11R,12R,13R,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10,12-dihydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,5,7,11,13,14-hexamethyl-9-methylidene-oxacyclotetradecan-2-one | 1370611-92-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R,6S,7S,10S,11R,12R,13R,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10,12-dihydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,5,7,11,13,14-hexamethyl-9-methylidene-oxacyclotetradecan-2-one
• CAS: 1370611-92-9
• 化学式: C₃₅H₆₃NO₁₁
• 分子量: 673.885
• InChiKey: WHKOVLXQMZDBAS-HBFYLZSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  47
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  8-methylene-oleandomycin 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 反应 6.5h， 以61%的产率得到(3R,4S,5R,6S,7S,10S,11R,12R,13R,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10,12-dihydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,5,7,11,13,14-hexamethyl-9-methylidene-oxacyclotetradecan-2-one
  参考文献：
  名称：

  Impact of stereochemistry on the biological activity of novel oleandomycin derivatives

  摘要：

  A set of 8-methylene-, 8-methyl-, and 8-methyl-9-dihydro-oleandomycin derivatives having different combinations of stereochemistries at positions C-8 and/or C-9 have been prepared in a chemoselective and stereoselective manner and tested in vitro for antibacterial activity and inhibition of IL-6 production. Configurations of the stereocenters at C-8 and C-9 were determined using 2D NMR techniques. We have shown that change of stereochemistry at these positions can exert a major influence on antibacterial activity as well as IL-6 inhibition, providing novel macrolide derivatives with diminished antibacterial and potent anti-inflammatory activity. In addition, the anti-inflammatory activity observed in vitro was confirmed in an in vivo model of lipopolysaccharide-induced inflammation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.013

文献信息

• Impact of stereochemistry on the biological activity of novel oleandomycin derivatives
  作者：Jurica Bauer、Mark Vine、Ilija Čorić、Martina Bosnar、Ivanka Pašalić、Gordana Turkalj、Gorjana Lazarevski、Ognjen Čulić、Goran Kragol

  DOI：10.1016/j.bmc.2012.02.013

  日期：2012.4

  A set of 8-methylene-, 8-methyl-, and 8-methyl-9-dihydro-oleandomycin derivatives having different combinations of stereochemistries at positions C-8 and/or C-9 have been prepared in a chemoselective and stereoselective manner and tested in vitro for antibacterial activity and inhibition of IL-6 production. Configurations of the stereocenters at C-8 and C-9 were determined using 2D NMR techniques. We have shown that change of stereochemistry at these positions can exert a major influence on antibacterial activity as well as IL-6 inhibition, providing novel macrolide derivatives with diminished antibacterial and potent anti-inflammatory activity. In addition, the anti-inflammatory activity observed in vitro was confirmed in an in vivo model of lipopolysaccharide-induced inflammation. (C) 2012 Elsevier Ltd. All rights reserved.