1-(hydroxymethyl)-10β-acetoxysinomenine | 1240580-85-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(hydroxymethyl)-10β-acetoxysinomenine
• 英文别名: 1-hydroxymethyl-10β-acetoxysinomenine
• CAS: 1240580-85-1
• 化学式: C₂₂H₂₇NO₇
• 分子量: 417.459
• InChiKey: KVKGSZBJWLPJMV-IPYGTTCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105.53
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  甲醇 、 碘苯二乙酸 、 1-hydroxymethyl sinomenine 在 碳酸氢钠 作用下， 以54%的产率得到1-(hydroxymethyl)-10β-methoxysinomenine
  参考文献：
  名称：

  SINOMENINE DERIVATIVES, SYNTHETIC METHODS AND USES THEREOF

  摘要：

  该发明涉及青藤碱衍生物，其合成方法及应用。青藤碱衍生物包括氧化衍生物和C-10取代的青藤碱衍生物。基于青藤碱结构上易氧化的酚基团，可以利用氧化、氧化去芳香化或共轭加成芳香化来引入C-10取代基以合成青藤碱衍生物。该发明的青藤碱衍生物具有以下结构：通过体外TNF-α抑制实验，评估了合成化合物的活性。这些实验结果表明，大多数化合物具有抗炎作用，有些化合物的活性优于青藤碱。这些化合物可用于治疗类风湿性关节炎等免疫性疾病。

  公开号：

  US20120308589A1

文献信息

• Regio- and stereoselective C10β–H functionalization of sinomenine: an access to more potent immunomodulating derivatives
  作者：Yang-Tong Lou、Li-Yan Ma、Meng Wang、Dongsheng Yin、Ting-Ting Zhou、Ai-Zhong Chen、Zhao Ma、Chao Bian、Shaozhong Wang、Zhen-Yu Yang、Bing Sun、Zhu-Jun Yao

  DOI：10.1016/j.tet.2012.01.009

  日期：2012.3

  Regio- and stereoselective C-10 beta-H functionalization of sinomenine, an economically available natural immunomodulating alkaloid, has been studied, developed and successfully applied to the synthesis of new immunosuppressive sinomenine derivatives in a protecting-free fashion. Regioselective oxidation of sinomenine with (diacetoxylodo)benzene (DIB) in water provided a single stable benzoquinone derivative 4, and subsequent 1,6-conjugated addition of 4 with alcohols, amines, and thiols afforded a new series of C-10 beta-H functionalized sinomenine derivatives stereoselectively. Some derivatives with a newly introduced 10 beta-bezenesulfanyl substituent exhibited much higher TNF-alpha inhibitory potency than their natural parent sinomenine. This work opens a convenient access to novel sinomenine derivatives with medicinal interests. (C) 2012 Elsevier Ltd. All rights reserved.