EM906 | 1313489-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: EM906
• 英文别名: (1S,2S,3R,6R,7S,8S,9R,10R,12R)-3-acetyl-9-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-7-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,6,8,10,12-pentamethyl-4,13-dioxabicyclo[8.2.1]tridecan-5-one
• CAS: 1313489-76-7
• 化学式: C₃₄H₅₉NO₁₁
• 分子量: 657.843
• InChiKey: YLJKDZXDCYUKRR-MTKFTCTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  EM906 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以93%的产率得到EM907
  参考文献：
  名称：

  Novel 12-membered non-antibiotic macrolides from erythromycin A; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents

  摘要：

  Herein, we report the design and synthesis of the novel 12-membered non-antibiotic macrolide (8R,9S)-8,9- dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin A (EM900), which was found to be a potent anti-inflammatory and/or immunomodulatory agent, capable of promoting monocyte to macrophage differentiation. This molecule shows improved acid stability, does not exhibit any anti-bacterial activity and has relatively low cytotoxicity against THP-1 cells. In addition, one of its analogues, (8R, 9S)-4 '',13-O-diacetyl- 8,9-dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin A (EM911), was found to be twice as effective as EM900. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.004
• 作为产物：
  描述：

  (8R,9S)-8,9-dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin 在 lead(IV) tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以75%的产率得到EM906
  参考文献：
  名称：

  Novel 12-membered non-antibiotic macrolides from erythromycin A; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents

  摘要：

  Herein, we report the design and synthesis of the novel 12-membered non-antibiotic macrolide (8R,9S)-8,9- dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin A (EM900), which was found to be a potent anti-inflammatory and/or immunomodulatory agent, capable of promoting monocyte to macrophage differentiation. This molecule shows improved acid stability, does not exhibit any anti-bacterial activity and has relatively low cytotoxicity against THP-1 cells. In addition, one of its analogues, (8R, 9S)-4 '',13-O-diacetyl- 8,9-dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin A (EM911), was found to be twice as effective as EM900. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.004

文献信息

• Novel 12-membered non-antibiotic macrolides from erythromycin A; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents
  作者：Akihiro Sugawara、Akito Sueki、Tomoyasu Hirose、Kenichiro Nagai、Hiroaki Gouda、Shuichi Hirono、Hideaki Shima、Kiyoko S. Akagawa、Satoshi Ōmura、Toshiaki Sunazuka

  DOI：10.1016/j.bmcl.2011.04.004

  日期：2011.6

  Herein, we report the design and synthesis of the novel 12-membered non-antibiotic macrolide (8R,9S)-8,9- dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin A (EM900), which was found to be a potent anti-inflammatory and/or immunomodulatory agent, capable of promoting monocyte to macrophage differentiation. This molecule shows improved acid stability, does not exhibit any anti-bacterial activity and has relatively low cytotoxicity against THP-1 cells. In addition, one of its analogues, (8R, 9S)-4 '',13-O-diacetyl- 8,9-dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin A (EM911), was found to be twice as effective as EM900. (C) 2011 Elsevier Ltd. All rights reserved.