4-O-caproylsinomenine | 1351933-01-1

• 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: 4-O-caproylsinomenine
• 英文别名: 4-Caproyl-Sinomenine；[(1R,9S,10S)-4,12-dimethoxy-17-methyl-13-oxo-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-3-yl] hexanoate
• CAS: 1351933-01-1
• 化学式: C₂₅H₃₃NO₅
• 分子量: 427.541
• InChiKey: NLLBOELERZPVJM-FUMQJTLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  己酸 、 青藤碱 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到4-O-caproylsinomenine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel sinomenine derivatives as anti-inflammatory agents

  摘要：

  Sinomenine (1) is clinically available for the treatment of rheumatoid arthritis (RA), however, its efficacy is quite weak. In the present study, a library of novel sinomenine-based homodimers and monomers through variable-length linkers were designed and synthesized, and their bioactivities were evaluated using RAW264.7 cells and mice. Among the compounds, 2f and 3b possessed much more potent inhibitory effects on the production of nitric oxide (NO), interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-alpha) than 1. Preliminary mechanism investigation revealed that 3b inhibited nuclear factor-kappa B (NF-kappa B) signaling pathway specifically, 2f suppressed both NF-kappa B and mitogen-activated protein kinase (MAPK) cascades. Moreover, 3b and 2f significantly alleviated the lipopolysaccharide (LPS)-induced mortality. These two compounds might serve as valuable candidates for anti-inflammatory drug discovery. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.036

文献信息

• Synthesis and biological evaluation of novel sinomenine derivatives as anti-inflammatory agents
  作者：Peng Teng、Hai-Liang Liu、Lei Zhang、Li-Li Feng、Yue Huai、Zhang-Shuang Deng、Yang Sun、Qiang Xu、Jian-Xin Li

  DOI：10.1016/j.ejmech.2012.01.036

  日期：2012.4

  Sinomenine (1) is clinically available for the treatment of rheumatoid arthritis (RA), however, its efficacy is quite weak. In the present study, a library of novel sinomenine-based homodimers and monomers through variable-length linkers were designed and synthesized, and their bioactivities were evaluated using RAW264.7 cells and mice. Among the compounds, 2f and 3b possessed much more potent inhibitory effects on the production of nitric oxide (NO), interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-alpha) than 1. Preliminary mechanism investigation revealed that 3b inhibited nuclear factor-kappa B (NF-kappa B) signaling pathway specifically, 2f suppressed both NF-kappa B and mitogen-activated protein kinase (MAPK) cascades. Moreover, 3b and 2f significantly alleviated the lipopolysaccharide (LPS)-induced mortality. These two compounds might serve as valuable candidates for anti-inflammatory drug discovery. (C) 2012 Elsevier Masson SAS. All rights reserved.