Sinomenin

• 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: Sinomenin
• 英文别名: sinomenine；(1R,9S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: INYYVPJSBIVGPH-MALMCIGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Sinomenin 在 palladium diacetate N-碘代丁二酰亚胺 、 copper(l) iodide 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  An inexpensive fluorescent labeling protocol for bioactive natural products utilizing Cu(I)-catalyzed Huisgen reaction

  摘要：

  Labeling of bioactive small molecules with organic dyes for various applications in cell biology has been emerging as an attractive research field. Using an easily prepared and inexpensive fluorescein derivative 1 and a Cu(I)-catalyzed Huisgen reaction, an efficient fluorescent labeling strategy is developed generally for bioactive natural products. Essentials of a successful labeling include the personalized introduction of an azido functionality to specific targets by a selective and efficient manner, and the strategic adjustment of reaction sequence to avoid possible side reactions under the 'click' reaction conditions. Such a protocol has been successfully applied to the fluorescent labeling of four bioactive small molecules in different chemical categories in this study. Advantages of this labeling protocol include the use of inexpensive reagents, ease of operation, free-of-protections at the 'click' step, and suiting a wide range of bioactive molecules bearing the reactive functionalities. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.069

文献信息

• SINOMENINE DERIVATIVES, SYNTHETIC METHODS AND USES THEREOF
  申请人：Yao Zhujun

  公开号：US20120308589A1

  公开（公告）日：2012-12-06

  The invention relates to sinomenine derivatives, methods for their synthesis and their applications. The sinomenine derivatives include oxidation derivatives, and C-10 substituted sinomenine derivatives. Based on the readily oxidizable phenol group on sinomenine structure, using oxidation, oxidative dearomatization, or conjugated addition aromatization, one can introduce C-10 substitutions to synthesize the sinomenine derivatives. The sinomenine derivatives of the invention have the following structures: Using in vitro TNF-α inhibition assay, the activities of the synthetic compounds are assessed. Results from these assays shown that most compounds have anti-inflammatory effects, and some compounds have better activities than that of sinomenine. These compounds may be used in treating immune diseases such as rheumatoid arthritis (RA).

  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。
• 10.1039/d4sc04461d
  作者：Shi, Haofeng、Zhang, Jingran、Li, Xuemin、He, Jiaxin、Sun, Yuli、Wu, Jialiang、Du, Yunfei

  DOI：10.1039/d4sc04461d

  日期：——

  direct halogenation of certain neutral or unreactive substrates by using solely the regular halogenating reagents has proven challenging. Although various halogenation approaches via activating halogenating reagents or substrates have emerged, a catalytic system enabling broad substrate applicability and diverse halogenation types remains relatively underexplored. Inspired by the halogenation of arenes

  有机卤化物是重要的有机构件，其应用涵盖各个领域。然而，仅使用常规卤化试剂直接卤化某些中性或非反应性底物已被证明具有挑战性。尽管已经出现了通过活化卤化试剂或底物的各种卤化方法，但能够实现广泛的底物适用性和多种卤化类型的催化系统仍然相对未得到充分探索。受芳烃噻蒽醌卤化芳烃的启发，我们在此报道，噻蒽醌与三氟甲磺酸（TfOH）结合使用，可以作为有效的催化系统来激活常规卤化试剂（NXS）。这种新方案可以完成多种类型的有机化合物的卤化，包括芳烃、烯烃、炔烃和酮。机理研究表明，在 TfOH 存在下，NXS 与噻蒽反应原位形成高反应性亲电卤素噻蒽物种，对于有效的卤化过程至关重要。
• WO2007/70703
  申请人：——

  公开号：——

  公开（公告）日：——
• Sinomenine Derivatives and Preparation and Uses Thereof
  申请人：Wang Jie

  公开号：US20080318966A1

  公开（公告）日：2008-12-25

  The present invention relates to the preparation and pharmacological use of sinomenine derivatives of formula I. The approach disclosed herein is the modification of D ring by-substituting for R. Additional substitutions in the other rings are also provided herein. Several of the sinomenine derivatives have significantly greater anti-inflammation activity when compared with the parent compound.
• US7932264B2
  申请人：——

  公开号：US7932264B2

  公开（公告）日：2011-04-26