lupanine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 英文名称: lupanine
• 英文别名: (1R,2R,9R,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-6-one
• 化学式: C₁₅H₂₄N₂O
• 分子量: 248.368
• InChiKey: JYIJIIVLEOETIQ-YIYPIFLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  lupanine 在 盐酸 、 sodium tetrahydroborate 、 碘 、 magnesium 、 碘甲烷 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 2-(4’-hlorophenyl)sparteine
  参考文献：
  名称：

  New arylsparteine derivatives as positive inotropic drugs

  摘要：

  Positive inotropic agents are fundamental in the treatment of heart failure; however, their arrhythmogenic liability and the increased myocardial oxygen demand strongly limit their therapeutic utility. Pursuing our study on cardiovascular activities of lupin alkaloid derivatives, several 2-(4-substituted-phenyl)-2-dehydrosparteines and 2-(4-substituted-phenyl) sparteines were prepared and tested for inotropic and chronotropic activities on isolated guinea pig atria. Four compounds (6b, 6e, 7b, and 7f) exhibited significant inotropism that, at the higher concentrations, was followed by negative inotropism or toxicity. Compound 7e (2-(4-tolyl) sparteine) exhibited a steep dose-depending inotropic activity up to the highest concentration tested (300 mu M) with an E-max of 116.5 +/- 3.4% of basal force, proving less potent but much more active in comparison to the highest concentrations tested of digoxin and milrinone having Emax of 87.5 +/- 3.1% and 52.2 +/- 1.1%, respectively. Finally, docking studies suggested that the relevant sparteine derivatives could target the sigma-1 receptor, whose involvement in cardiac activity is well documented.

  DOI：

  10.1080/14756366.2017.1279156

文献信息

• Products of the reactions of sparteine-2-thione with CuBr2 in protic and aprotic solvents
  作者：Urszula Rychlewska、Beata Warżajtis、Beata Jasiewicz、Tomasz Toliński

  DOI：10.1016/j.poly.2010.11.023

  日期：2011.2

  Reactions of copper(II) bromide with racemic sparteine-2-thione (SSp) in a 1:1 M ratio yielded two new complexes, whose structures depend on the solvent used. In acetonitrile, the reaction product is a sulfur-bridged dinuclear [CuBr2(mu-SSp)](2) complex (1) in which sparteine-2-thione acts as a bridging S-ligand, while in methanol it is a CuBr2 complex (2) with sparteine deprived of the A-ring. Compound 1 crystallizes as an acetonitrile solvate in a 1:2 ratio and constitutes one of a few Cu(II) doubly bridged heterocyclic thionato complexes. The disorder of the C/D bisquinolizidine fragment in the crystal of 1 reflects the ease of the conversion from the common trans boat-chair to the unprecedented cis chair-boat stereoisomer. Obtained in methanol, the sparteine surrogate (Sp(surr)), is equally effective as a chelating ligand as sparteine and its isomers, and thus can be used as an alternative diamine ligand in metal complexation. Metal coordination with Sp(surr) brings the diamine nitrogens much closer together than in any other sparteine metal complexes. (C) 2010 Elsevier Ltd. All rights reserved.
• New arylsparteine derivatives as positive inotropic drugs
  作者：Vito Boido、Marcella Ercoli、Michele Tonelli、Federica Novelli、Bruno Tasso、Fabio Sparatore、Elena Cichero、Paola Fossa、Paola Dorigo、Guglielmina Froldi

  DOI：10.1080/14756366.2017.1279156

  日期：2017.1.1

  Positive inotropic agents are fundamental in the treatment of heart failure; however, their arrhythmogenic liability and the increased myocardial oxygen demand strongly limit their therapeutic utility. Pursuing our study on cardiovascular activities of lupin alkaloid derivatives, several 2-(4-substituted-phenyl)-2-dehydrosparteines and 2-(4-substituted-phenyl) sparteines were prepared and tested for inotropic and chronotropic activities on isolated guinea pig atria. Four compounds (6b, 6e, 7b, and 7f) exhibited significant inotropism that, at the higher concentrations, was followed by negative inotropism or toxicity. Compound 7e (2-(4-tolyl) sparteine) exhibited a steep dose-depending inotropic activity up to the highest concentration tested (300 mu M) with an E-max of 116.5 +/- 3.4% of basal force, proving less potent but much more active in comparison to the highest concentrations tested of digoxin and milrinone having Emax of 87.5 +/- 3.1% and 52.2 +/- 1.1%, respectively. Finally, docking studies suggested that the relevant sparteine derivatives could target the sigma-1 receptor, whose involvement in cardiac activity is well documented.