(1R,9S,10S)-15-methoxy-20-methyl-5-(3-nitrophenyl)-4,6,20-triazapentacyclo[8.7.3.01,9.03,7.012,17]icosa-3(7),5,12(17),13,15-pentaen-16-ol | 902137-68-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: (1R,9S,10S)-15-methoxy-20-methyl-5-(3-nitrophenyl)-4,6,20-triazapentacyclo[8.7.3.01,9.03,7.012,17]icosa-3(7),5,12(17),13,15-pentaen-16-ol
• CAS: 902137-68-2
• 化学式: C₂₅H₂₆N₄O₄
• 分子量: 446.506
• InChiKey: PIGUNZZGSFXUQE-HUJREVKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  间硝基苯甲醛 、 Sinomeninon 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以82%的产率得到(1R,9S,10S)-15-methoxy-20-methyl-5-(3-nitrophenyl)-4,6,20-triazapentacyclo[8.7.3.01,9.03,7.012,17]icosa-3(7),5,12(17),13,15-pentaen-16-ol
  参考文献：
  名称：

  Modification of poorly bioactive sinomenine into more potent immunosuppressive agents by embedding of drug-like fragments

  摘要：

  Embedment of drug-like heterocyclic moieties was Successfully employed in the novel modification of the readily available but poorly bioactive natural alkaloid sinomenine. Application of the newly proposed approach afforded a number of more potent sinomenine-like molecules with a significantly high hit rate. Among these new analogous, up to 500-fold increase of in vitro immunosuppressive activity was achieved. Further biological experiments of representative compound 4b indicated that it might inhibit NF-kappa B activation induced by TNF-alpha in a dose dependent way and showed remarkable in vivo treatment effects against the mouse experimental autoimmune uveoretinitis (EAU) disease models. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.019

文献信息

• Modification of poorly bioactive sinomenine into more potent immunosuppressive agents by embedding of drug-like fragments
  作者：Yang-Tong Lou、Hai-Bin Zhou、Jia Zou、Ling-Chen Yan、En-Guan Bi、Bing Sun、Zhu-Jun Yao

  DOI：10.1016/j.tetlet.2009.11.019

  日期：2010.1

  Embedment of drug-like heterocyclic moieties was Successfully employed in the novel modification of the readily available but poorly bioactive natural alkaloid sinomenine. Application of the newly proposed approach afforded a number of more potent sinomenine-like molecules with a significantly high hit rate. Among these new analogous, up to 500-fold increase of in vitro immunosuppressive activity was achieved. Further biological experiments of representative compound 4b indicated that it might inhibit NF-kappa B activation induced by TNF-alpha in a dose dependent way and showed remarkable in vivo treatment effects against the mouse experimental autoimmune uveoretinitis (EAU) disease models. (C) 2009 Elsevier Ltd. All rights reserved.